Maui

No. 241

Partial ocean view 1 bedroom condo, AC, beachfront

Vacation Rental

1 bedroom sleeps 4 private pool about $92 a night

Welcome to Nani Kai Hale 403. Make your Maui memories from this 4th floor 1 bedroom partial ocean view beachfront condo. Feel right at home with everything from split AC in both the living room & bedroom, sofa sleeper, fully equipped kitchen, some beach gear, & luxury organic essentials. This condo can accommodate 4 guests with its bedroom, sofa sleeper, and 2 full bathrooms. Situated on a 6 mile stretch of sandy beach in N Kihei the possibilities are endless for ocean activities. This resort features pool, BBQs, & direct beach access. Book today! Partial ocean view updated 1 bedroom, 2 bathroom condo on the 6 mile stretch of sandy Sugar Beach.

Check rates on Whimstay →

No. 242

OceanFront 1BD Amazing Ocean Views - Maalaea Banyans 203

Oceanfront

1 bedroom sleeps 4

Welcome to Your Maui Retreat: Looking for an unbeatable ocean view in a quiet, relaxing location? Maalaea Banyans 203 is oceanfront, and has a great sandy beach within walking-distance.

Check rates on Vrbo →

No. 243

Breathtaking Views and Outdoor Pool - Stunning Oceanfront Oasis

Condo

1 bedroom sleeps 4 private pool about $156 a night

Escape to Island Surf 304, a fully renovated 1-bedroom, 1-bath ocean-view condo in the heart of Kihei. This modern South Maui retreat is designed for comfort, convenience, and easy island living, with a bright open floor plan, clean contemporary finishes, and a private lanai overlooking the ocean. Start your morning with coffee outside, check the surf and ocean conditions from the lanai, then settle into a relaxed Maui day. Inside, the condo comfortably sleeps up to 4 guests with a plush king bed in the bedroom and a sleeper sofa in the living area.

Check rates on Whimstay →

No. 244

Stunning Oceanfront 1bd - Maalaea Kai 315

Oceanfront

1 bedroom

Guests enjoy the stunning beach views at this property.

Check rates on Vrbo →

No. 245

Direct oceanfront condo, AC, 6 mile sandy beach

Vacation Rental

1 bedroom sleeps 4 private pool about $161 a night

Welcome to Sugar Beach 531. This oceanfront 1 bedroom, 1 bathroom condo can accommodate 4 people. Enjoy ocean views throughout this unit & from your private lanai. Feel right at home with everything from central AC to in unit washer/dryer, & essentials. Situated on a 6 mile stretch of white sand beach the possibilities are endless for ocean activities. The resort also features an onsite restaurant/pub, tour/rental bookings, & more. There's no better place to make your Maui memories. Book today! WHY YOU’LL LOVE IT. Direct oceanfront condo with unobstructed views of Maui’s longest beach. Coastal style interior with modern upgrades and open layout.

Check rates on Whimstay →

No. 246

Oceanfront, King Bed, Split AC, WiFi, Hot Tub Pool

Oceanfront

1 bedroom sleeps 3

Escape to Paradise in Maui! Enjoy the solitude of a resort far from the crowded high-rise hotels and traffic.

Check rates on Vrbo →

No. 247

Charming Condo with Modern Amenities - Serene Island Retreat

Condo

1 bedroom sleeps 4 private pool about $162 a night

The new roof project will take place over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building. From the front door, a magical stretch of Maui beach awaits your exploration - and inside, this condo has been beautifully remodeled from top to bottom, with all sparkling new furnishings, surfaces, and fixtures. Kihei Garden Estates B-103, a ground level unit in Building B at Kihei Garden Estates, features a painted and polished concrete flooring and counters set the tone for tasteful, understated elegance, and no expense has been spared to create the ultimate home base for your Maui adventure.

Check rates on Whimstay →

No. 248

Breathtaking Ocean Views and Beachfront Oasis - Stunning Coastal Haven

Condo

1 bedroom sleeps 4 private pool about $170 a night

. Remodeled BeachFront 1BR, 2BA Superb Ocean Views, Split AC, BeachFront Pool BBQ and Loungers. Sandy Beach Walks-Nani Kai Hale 605 Welcome to Your Maui Retreat: Breathe in fresh ocean breezes from your oceanfront lanai and sip on a morning cup of coffee, then take a stroll down the beach. The soft sand beach is walkable year-round. Experience all the comforts of home from our beautifully renovated Nani Kai Hale 605 with comfortable furnishings and full size stainless steel appliances. The perfect oceanfront home for your next Maui vacation!.

Check rates on Whimstay →

No. 249

Luxurious Oceanfront Escape with Stunning Views - Exquisite Maui Retreat

Condo

1 bedroom sleeps 4 private pool about $339 a night

A unit renovation will take place in unit 310, next door to this unit, beginning April 7th through September 15th. Please expect noise as well as the potential for dust and debris during work hours. Royal Mauian 309 is a newly renovated luxury condo for the guest who wants a total immersion in Maui's ultimate beach experience. Sitting less than 50 feet from the pristine Pacific and is flanked by two of Maui's postcard beaches - Kamaole I and Kamaole II. Off the elevator, it's a 30-second walk in either direction to the soft, golden sand and warm-water swimming and snorkeling that only Maui's south shore can offer. Everything is brand new, beautifully done, and totally renovated.

Check rates on Whimstay →

No. 250

Ocean Views and Beachfront Access - Stunning Maui Escape

Condo

1 bedroom sleeps 2 private pool about $357 a night

Enjoy unparalleled ocean views from this top floor unit, Kihei Beach Condominium 606. Beautifully remodeled, beach front, and overlooking Maui's longest golden sand beach. Start and end each Maui day with panoramic views that take in the Pacific far beyond the visible outer islands, watch whales leap from the ocean in season, and enjoy a fully immersed ocean experience for two during your Maui stay. Less than 30 seconds from your feet in the sand at stunning Sugar Beach, which spans six miles, and invites those leisurely morning and sunset beach walks.

Check rates on Whimstay →

No. 251

Tranquil Oceanfront Escape with Heated Pool - Stunning Ocean Views

Condo

1 bedroom sleeps 4 private pool about $122 a night

Welcome to Your Oceanfront Maui Retreat: Nestled along the tranquil shores of Māʻalaea Bay, Island Sands 210 invites you into a front-row seat to Maui's natural beauty, where sweeping ocean views and the gentle sound of the waves create an atmosphere of pure relaxation. Aloha and E Komo Mai! Welcome to your oceanfront sanctuary, where every moment is infused with tranquility and natural splendor. Whether you're seeking a centrally located home base for your Maui adventures or an intimate romantic escape, Island Sands 210 offers the perfect backdrop to explore, reconnect, and create unforgettable memories.

Check rates on Whimstay →

No. 252

Oceanfront Access and Beachfront Bliss - Exquisite Coastal Escape

Condo

1 bedroom sleeps 4 private pool about $88 a night

Welcome to your oceanfront Maui retreat, where breathtaking views, unbeatable convenience, and island comfort come together to create the perfect Hawaiian getaway. Ideally situated on the first floor, this beautifully appointed condo places you just steps from the sparkling pool, sandy beach, and community barbecue area, allowing you to fully embrace Maui's laid-back coastal lifestyle from the moment you arrive. Wake each morning to the soothing sounds of the ocean and spend your days enjoying easy access to the beach, whether you're swimming, snorkeling, paddleboarding, or simply relaxing under the Hawaiian sun.

Check rates on Whimstay →

No. 253

Oceanfront resort 10th floor 1 bedroom condo, AC

Vacation Rental

1 bedroom sleeps 4 private pool about $92 a night

Welcome to Royal Kahana 1009. This spacious (777 square feet with a 150-square-foot lanai) 10th floor 1 bedroom, 1 bathroom condo offers some of the best views on the westside. The private lanai overlooks the beautiful Pacific Ocean & both Islands of Lanai and Molokai. The Master Bedroom has a California king bed & the Living Area has a queen sleeper sofa. The condo accommodates 4 guests. Keep cool with Central Air & ceiling fans throughout the unit. Make you Maui memories here @ RK 1009. WHY YOU’LL LOVE IT. 10th-floor oceanfront views of the Pacific and the islands of Lāna‘i & Moloka‘i. Spacious 1BR / 1BA condo (777 sq ft + 150 sq ft lanai), sleeps 4.

Check rates on Whimstay →

No. 254

Royal Kahana 612

Vacation Rental

1 bedroom sleeps 4 private pool about $92 a night

Welcome to Royal Kahana 612. This oceanfront spacious 6th floor 1 bedroom, 1 bathroom condo offers stunning ocean & surrounding island view. This condo features a remodeled full stocked kitchen with stainless appliances, tastefully decorated, & can accommodate 4 guests. Keep cool year round with central AC & ceiling fans throughout. This resort offers many amenities and located in a great neighborhood close to food truck parks, shops, farmers market, & more. Book this oceanfront gem today! WHY YOU’LL LOVE IT. 6th-floor oceanfront condo with breathtaking views of Moloka‘i and Lāna‘i. Spacious 1BR / 1BA (sleeps 4) with California King bed and queen sofa sleeper.

Check rates on Whimstay →

No. 255

Oceanfront Serenity and Spacious Kitchen - Stunning Maui Escape

Condo

1 bedroom sleeps 4 private pool about $100 a night

Oceanfront 1 bedroom unit with spacious kitchen and tile floors throughout, overlooking the ocean in Kahana. Includes iPhone dock, TV, and free WiFi. Enjoy evening sunset views and lanai dining. Condo features Cal King Bed and Queen Sofa Sleeper. This Maui vacation resort is located just seven miles north of the old whaling capital of Lahaina in West Maui. Set on a quiet, picturesque Kahana Beach, you can unwind as you swim in the cool ocean, and stroll along the beach at sunset. Enjoy the comfort of grilling by the courtyard pool and convenience of walking to dining, shopping, activities and beach rentals at the nearby Kahana Gateway Center.

Check rates on Whimstay →

No. 256

Ocean Views and Heated Pool - Stunning Oceanfront Sanctuary

Condo

1 bedroom sleeps 4 private pool about $102 a night

Oceanfront Tropical 1Bedroom Condo with Heated Pool, AC, Furnished Lanai and Stunning Ocean Views for Year Round Indoor-Outdoor Living - Kaleialoha 309 Welcome to your Maui Retreat: Come stay at the Kaleialoha Oceanfront Condominium! Kaleialoha 309 is a direct oceanfront 1 bedroom, 1 bathroom condo that offers the best of Hawaiian style living just a stone's throw away from the beautiful blue Pacific Ocean. Enjoy the sounds of the waves right off your lanai, while you watch turtles year round, humpback whales playing offshore during Hawaii's whale season, and amazing evening sunsets.

Check rates on Whimstay →

No. 257

Oceanfront Lanai and Heated Pool - Stunning Tropical Paradise

Condo

1 bedroom sleeps 4 private pool about $102 a night

Direct oceanfront 1 Bedroom/1Bath Condo Hawaiian Style Tropical Paradise - Kaleialoha 210 Welcome to your Maui Retreat: Enjoy the view from your private lanai and see the beautiful pacific ocean and the neighboring islands in the near distance. Kaleialoha 210 is a spacious 1 bedroom, 1 bathroom condominium that has all of the comforts of home for you to enjoy while visiting Maui. This condo sleeps up to 4 guests and features AC in the living room and a kitchen with full-sized appliances to make dining easy and comfortable.

Check rates on Whimstay →

No. 258

Oceanfront Escape with Stunning Views and Complimentary Activities - Amazing Retreat

Condo

1 bedroom sleeps 4 private pool about $182 a night

Papakea L108 Remodeled 1BR 1BA Oceanfront Ground Floor Corner Condo Sleeps Up To 4! Papakea L108 is a renovated and updated 1-bedroom, 1-bathroom oceanfront condo that sleeps up to 4 guests. This spacious ground floor corner unit has lots of windows for light and the island breezes. From your private lanai, you have a lovely area to sit and dine or relax with nothing but the crystal blue ocean and the famous Maui sunsets in front. Take just a few steps, and you'll be at the ocean's edge. Your home away from home is waiting! NO RESORT OR PARKING FEES!

Check rates on Whimstay →

No. 259

Ocean View and Gourmet Kitchen - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 private pool about $226 a night

FROM THE MOMENT YOU ENTER, you will be surrounded by the spirit of Aloha. This is not your average 1-bedroom Papakea unit, as F310 is only one of 12 units of its kind, ocean front with extra square footage on the inside, extra space on the wrap around lanai, and a 180-degree view from TWO sides. Your first impression, once you enter and glance to the right, is the deep blue color of the Pacific Ocean and the outer islands of Moloka’i and Lana’i from 3 sides of the room (west window, north window and mirrors on the entire south side of the living area).

Check rates on Whimstay →

No. 260

Panoramic Views and Elegant Kitchen - Spectacular Oceanfront Escape

Condo

1 bedroom sleeps 4 about $415 a night

Oceanfront corner condo with panoramic views from Lanai to Molokai - unobstructed sunset views any time of the year. At dusk, tiki torches light the path to the water where the sun sets between the neighbor isles of Lanai and Molokai. Located on the third floor, this one-bedroom, one-bath unit with wraparound lanai is under new ownership, and is a real gem! Beautifully updated kitchen with maple cabinets and granite countertops, and well-provisioned for cooking and dining in. This unit offers casual elegance and amazing views. the property manager prides itself in providing you the best experience during your stay.

Check rates on Whimstay →

No. 261

Charming Ground-Floor Oasis with Pools and Daily Activities - Gorgeous Retreat

Condo

1 bedroom sleeps 2 private pool about $184 a night

Wailea Ekahi 32B is a gorgeous ground-floor condo that sleeps up to 2 guests, perfect for a romantic getaway. Wailea Ekahi is located on the beautiful south side of Maui. You will love staying at this beachfront resort, near restaurants and shops. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences, plus unbeatable savings on other local favorites! This exclusive benefit is offered in partnership with Xplorie, giving you an easy way to add adventure, relaxation, and local flavor to your stay.

Check rates on Whimstay →

No. 262

Wailea Ekahi Village 18C

Condo

1 bedroom sleeps 4 shared pool about $231 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 18C A spacious 1,000 sq.ft. 1-bedroom condo with 2 full bathrooms, and step-free ground-floor walkout access to a covered wrap-around lanai. Enjoy serene garden views with distant ocean glimpses, 4 resort pools, and a 5 to 10-minute stroll down scenic botanical paths to resort's oceanfront pavilion at Keawakapu Beach. Perfect for small families and couples with a king bed, sleeper sofa, and beach gear provided. WHY OUR GUESTS LOVE IT. Lush Garden Setting: Relax on your private covered wrap-around lanai surrounded by lush grounds and beautiful garden views. Spacious 1,000 sq.ft.

Check rates on Whimstay →

No. 263

Tropical Oasis with Expansive Lanai - Serene Island Retreat

Condo

1 bedroom sleeps 2 private pool about $352 a night

*. *. The Wailea Ekahi main pool area will be closed for renovations from August 10, 2026 to October 15, 2026. The 3 other pools on property will remain open during this time. *. * Welcome to Wailea Ekahi 4E, a serene one-bedroom, one-bathroom retreat nestled in the heart of Maui's lush Wailea coast. Perched on the second floor of a low-rise building, this corner unit offers a private and peaceful setting, surrounded by tropical greenery and just steps away from the soft sands of Keawakapu Beach. Inside, the condo boasts an open floor plan with vaulted, wood-beamed ceilings that enhance the sense of space and light.

Check rates on Whimstay →

No. 264

Lush Landscaped Grounds and Relaxing Pools - Stunning Beachfront Haven

Condo

1 bedroom sleeps 4 private pool about $380 a night

Stay local, not corporate. Wailea Rentals presents: Wailea Ekahi Village - Ekahi means #1 in Hawaiian and that is exactly what Ekahi Village is - 1 of Wailea's top luxury beachfront condominium resorts. Located directly on Keawakapu Beach at the north end of Wailea on Maui's quiet, sunny, south side, Wailea Ekahi features 33 acres of beautiful, mature landscaped grounds in a low-rise, low-density village setting stretching from the beachfront pool up to Wailea Alanui Drive. This is definitely a resort complex you will remember and want to keep returning to year after year. Beach chairs, beach towels and coolers are provided.

Check rates on Whimstay →

No. 265

Oceanfront Retreat with Private Beach Cabana - Stunning Island Sanctuary

Condo

2 bedroom sleeps 8 private pool about $229 a night

This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances. Oceanfront Retreat - Private Beach Cabana, Golf Course Views, and Spacious Lanai E komo mai (welcome) to your island sanctuary, where the rhythm of the kai (ocean) and the warmth of the Hawaiian sun embrace you in true aloha. Nestled in lush gardens with breathtaking views of Nā Kai ʻEwalu (the Pacific Ocean) and the Kāʻanapali Golf Course, this 2-bedroom, 2-bathroom retreat invites you to slow down, reconnect, and create memories that will stay with you forever.

Check rates on Whimstay →

No. 266

Three Incredible Pools and Ocean Access - Luxurious Tropical Sanctuary

Condo

2 bedroom sleeps 6 private pool about $509 a night

Located beach front at North Kaanapali Beach, Honua Kai 934 is the newest and most luxurious vacation resort in West Maui. The concept is a hybrid of a luxury hotel with oversized, private condo living, and this amazing corner-end 9th floor unit showcases one of the best locations on this 32-acre tropical oasis. It's the only beach front resort built in West Maui in the last decade. Three incredible pools, with waterfalls, slides, spas, shallow play pool, and adult relaxation areas create an unmatched ocean front resort atmosphere.

Check rates on Whimstay →

No. 267

Breathtaking Views and Easy Beach Access - Stunning Oceanfront Retreat

Condo

2 bedroom sleeps 4 private pool about $364 a night

Remodeled- 2 BR-Stunning Ocean Views-Great Beach Access OCEANFRONT SUITE with WiFi, A/C, and EASY ACCESS TO TWO OF MAUI'S BEST BEACHES Step into comfort when you stay at this recently remodeled condominium on the top floor of the Royal Mauian where you will be greeted with breathtaking ocean views from your spacious outdoor covered balcony, your ‘lanai’. You are in the perfect spot to experience the beauty of Maui and relax with your friends and family. As you enter the property, you are welcomed by the airy open-plan living space. You will find a fully-equipped kitchen complete with stainless steel appliances and everything needed to prepare your favorite recipes.

Check rates on Whimstay →

No. 268

Beachfront Pool and Spacious Patio - Stunning Oceanfront Retreat

Condo

2 bedroom sleeps 6 private pool about $203 a night

. Spacious OceanFront 2Bedroom Ground Floor Condo with New Split AC System, BeachFront Pool, and Steps to The Ocean. - Lauloa 105 Welcome to your Maui Retreat: Watch the sunset from the comfort of your patio. See the Honu (Sea Turtles) and Humpback Whales play just outside your door or watch the surfers on the legendary surf break "Freight Trains" (the world's fastest surfable wave). Lauloa 105 is a beautiful 2-bedroom, 2-bathroom condo. With two master suites, everyone will be comfortable! This is a ground floor unit, so you can walk right out to the ocean or to the oceanfront pool! Sugar Beach is a 3-5 minute walk away and is the longest stretch of sandy beach on Maui.

Check rates on Whimstay →

No. 269

Oceanfront Serenity and Stunning Views - Exquisite Coastal Retreat

Condo

2 bedroom sleeps 6 private pool about $265 a night

Enjoy direct, forever ocean front views across Maalaea Bay, all the way to the outer islands, and experience a total seaside immersion just steps from the pristine Pacific in this well-maintained and newly renovated shore-front condo, which accommodates up to six guests comfortably. It fronts the longest walking beach on Maui, with protected warm-water swimming and snorkeling: enjoy a full-on beach day or explore a 5-mile beach hike featuring a bird sanctuary, deserted shoreline, and your own private ocean adventure.

Check rates on Whimstay →

No. 270

Oceanfront Lanai and Stunning Views - Exquisite Maui Escape

Condo

2 bedroom sleeps 6 private pool about $203 a night

Welcome to your Maui Retreat: This oceanfront condo is on the 3rd floor and has unobstructed views of Molokai and Lanai and Maui s incredible sunsets. This home away from home has 2-comfortable bedrooms, full kitchen, extra loft, 2-full bathrooms, and an oceanfront covered lanai for that additional indoor-outdoor living. Paradise is waiting at Kulakane 304!. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences plus unbeatable savings on other local favorites!

Check rates on Whimstay →

No. 271

Oceanfront Lawn and Stunning Sunsets - Exquisite Maui Retreat

Condo

2 bedroom sleeps 8 private pool about $242 a night

Papakéa Resort L106 Unbelievable Direct Oceanfront Lawn Location with Stunning Sunsets, Steps to the Pool & Jacuzzi Welcome to your Maui Retreat: This ground-floor, oceanfront two-bedroom, two-bath condo comfortably sleeps up to eight and is located in the coveted L Building of Papakea Resort in Kaanapali. Step from your private lanai onto a palm-studded lawn just a short stroll from the West Maui shoreline, perfect for sunset viewing, seasonal whale watching, and effortless beach days. With cafés, markets, and adventures just minutes away, Papakea L-106 offers the ideal blend of island relaxation and convenience. NO RESORT OR PARKING FEES!

Check rates on Whimstay →

No. 272

Oceanfront Oasis with Spectacular Views - Exquisite Maui Retreat

Condo

2 bedroom sleeps 6 private pool about $262 a night

NEW LISTING Amazing 2 Bedroom, 2 Bathroom, West Maui Beachfront Getaway Steps to the Beach, Pool, and Hot Tub! - Kahana Village 34 Welcome to your Maui Retreat: Wake up to the sound of waves and breathtaking views at this beautifully remodeled two-bedroom, two-bathroom, two-story condo at Kahana Village. This spacious West Maui retreat is the perfect blend of comfort, and location, that creates an inviting space for couples, families, or even friends traveling together. The first floor features a light and airy open-concept layout, seamlessly connecting the living, dining, and kitchen areas.

Check rates on Whimstay →

No. 273

Oceanview Sanctuary with Expansive Lanai and Resort Pools - Luxurious Oasis

Condo

2 bedroom sleeps 6 shared pool about $310 a night

This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances. Oceanfront Oasis - Wraparound Lanai, Chef's Kitchen & Resort Pools Hoʻokipa (hospitality) welcomes you to a luxurious retreat on the serene shores of West Maui. Perched on the 5th floor of a beautifully maintained resort, your two-bedroom, two-bathroom haven offers unobstructed ocean views, modern amenities, and a warm, inviting ambiance that embodies the essence of aloha (love and compassion). Whether you're traveling with your ʻohana (family) or enjoying a romantic escape, this is your gateway to a Hawaiian adventure filled with relaxation, discovery, and unforgettable moments.

Check rates on Whimstay →

No. 274

Ocean View and Resort Amenities - Stunning Beachfront Escape

Condo

1 bedroom sleeps 4 private pool about $95 a night

Spacious Ocean View Studio at Kaanapali Shores BeachFront Resort w/ Pools - Kaanapali Shores 942 Welcome to your Maui Retreat: Kaanapali Shores 942 is a top floor studio situated at an oceanfront resort in West Maui! This condo is fresh, clean, and spacious, sleeping up to 4 guests. You can work on the lanai from our beautiful condo with high-speed internet or take a break and enjoy the beautiful year-round sunshine with a walk on the beach You cannot beat this location, take advantage of all of the resort amenities that Kaanapali Shores has to offer, and you will see all the comforts of home right at your fingertips.

Check rates on Whimstay →

No. 275

Breathtaking Ocean Views and Tropical Bliss - Stunning Beachfront Escape

Condo

1 bedroom sleeps 2 private pool about $156 a night

Enjoy Breathtaking Ocean Views & Tropical Bliss at this Spacious Studio - Mahana 1113 Welcome to your Maui Retreat: When you first open the door at Mahana 1113, you are facing a wall of windows showcasing the panoramic views of endless waves and the islands of Lanai and Molokai in the distance. The Mahana at Kaanapali provides everything you need for your vacation in paradise. From the lanai you will often see turtles in the crystal-clear water, and from December through April watch humpback whales breach from the ocean. Bring your binoculars for a close-up, unobstructed view of the sea life. Watching turtles and whales from this vantage point feels like floating on top of the world.

Check rates on Whimstay →

No. 276

Panoramic Ocean Views and Luxurious Amenities - Exquisite Oceanfront Haven

Condo

1 bedroom sleeps 4 private pool about $211 a night

Beautiful Spacious & Remodeled 1BR 1BA Unit with Amazing Oceanfront Views - Maui Kai 601 Welcome to your Maui Retreat: Enjoy unbeatable panoramic views from this highly desirable 6th floor oceanfront corner unit on the Kaanapali coast. Watch gorgeous sunsets over Moloka'i and Lana'i every day from the comfort of your living room. Enjoy the brand new lanai, luxurious tile throughout the condo, gorgeous granite counters and all new appliances in the kitchen. Your vacation home comes equipped with everything you will need. Just pack your suitcase and that's it!.

Check rates on Whimstay →

No. 277

Charming Oceanfront Retreat with Garden Views - Cozy Island Getaway

Condo

1 bedroom sleeps 4 private pool about $97 a night

Island Style Updated 1Bedroom OceanFront Condo. Ground Floor for Easy Year-Round Indoor-Outdoor Living. Tropical Getaway to Relax and Recharge - Kauhale Makai 131 Welcome to your Maui Retreat: Kauhale Makai 131 has been thoughtfully updated to enhance your stay on the Valley Isle. The kitchen boasts modern stainless steel appliances, ensuring convenience and functionality, and the bathroom features a tastefully tiled shower, adding a touch of elegance to your daily routine. This cozy condo also offers a tranquil escape with a delightful garden view from the private lanai space.

Check rates on Whimstay →

No. 278

Oceanfront Escape and Stunning Views - Serene Island Haven

Condo

1 bedroom sleeps 4 private pool about $110 a night

Welcome to Lahaina Roads #210, your private oceanfront escape. Step into a fully remodeled unit with modern finishes throughout. Perched right above the Pacific, this one-bedroom condo offers uninterrupted views of Molokaʻi and Lānaʻi, Maui’s legendary sunsets, and in winter, incredible whale watching from your lanai. The resort itself is a hidden gem, intimate, relaxing, and full of island charm. Spend your days lounging at the oceanfront pool, grilling fresh island fish on the BBQ grills, or dining outdoors with the sound of the waves as your soundtrack. Inside, #210 is thoughtfully furnished to make you feel at home, with everything you need for a comfortable and memorable stay.

Check rates on Whimstay →

No. 279

Oceanview updated 1 bedroom coastal resort condo

Vacation Rental

1 bedroom sleeps 4 private pool about $92 a night

Welcome to Papakea K301. This updated Papakea Resort 1 bed, 1 bath fully stocked condo is in a great location with beautiful Ocean and Resort Views. This bright & airy condo has coastal vibes throughout & can accommodate 4 people. It comes with all the household items you'll need to make amazing Maui memories. The resort has amenities galore including tropical koi pond, putting greens, tennis and pickle ball courts, pools, spas, BBQ area, cabana, 24 hour front desk, ample parking, & more.

Check rates on Whimstay →

No. 280

Updated Oceanfront 1 bedroom West Maui condo

Vacation Rental

1 bedroom sleeps 4 private pool about $92 a night

Welcome to Hale Ono Loa 212. This freshly painted 1 bedroom, 1 bathroom updated condo will make you feel right at home. From the moment you walk in you'll see the ocean and feel the Maui vibes. This fully equipped unit can comfortably accommodate 4 people, offers a full kitchen, & ocean views from the entire unit, even the bedroom. Admire sunsets, whale watching, sailboats, & the island of Molokai right from your large private shaded lanai. This is the perfect place to make your Maui memories.

Check rates on Whimstay →

No. 281

Oceanfront Patio and Free Activities - Breathtaking Tropical Haven

Condo

1 bedroom sleeps 4 private pool about $95 a night

Welcome to your Maui Retreat: Aloha! Come and enjoy the breathtaking views from Kahana Reef 117! This is the perfect getaway for those that want to enjoy the matchless beauty of the Pacific Ocean while sitting on your patio. Easily watch seabirds flying by and sea turtles in the reef. Prime location for whale watching during season. Drift off to sleep to the sound of the ocean and the sea breeze. You will love this recently remodeled ground floor 1 bedroom, 1 bathroom home!. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences, plus unbeatable savings on other local favorites!

Check rates on Whimstay →

No. 282

Ocean Views and Luxurious Amenities - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 private pool about $107 a night

Welcome to your Maui Retreat! Make Valley Isle 401 your oceanfront home away from home for your next Maui vacation. With new living room and dining area furniture in Summer 2021, and breathtaking direct ocean views from the 4th floor our little slice of paradise creates the perfect place to make memories that will last a lifetime for you and your family or friends. Beautifully Remodeled OceanFront 1Bedroom, 1Bathroom with Amazing Sunset and Ocean Views.

Check rates on Whimstay →

No. 283

Direct Ocean Front and Breathtaking Views - Stunning Coastal Haven

Condo

1 bedroom sleeps 4 private pool about $144 a night

Direct Ocean Front! Sleep to the sound of the waves! West Maui Kaanapali Papakea A309 is a 1 bedroom, 1 bathroom, sleeps 4, third floor corner condo 25 feet from the ocean's edge. Watch the whales, sunsets, and the ocean from the kitchen, living room and lanai. Sleep to the sound of the waves. This condo is truly directly on the ocean. You awake to the sites and sounds of the beautiful surf, dine on your lanai while enjoying the whales and breathtaking sunsets, or simply relax with a refreshing cocktail and enjoy the views of the ocean, Moloka'i and Lana'i. Updated kitchen and bathroom with tile/granite counters. Living room air conditioner. Large stacked washer and dryer.

Check rates on Whimstay →

No. 284

Ocean Views and Cozy Lanai - Charming Oceanfront Retreat

Condo

1 bedroom sleeps 4 private pool about $146 a night

Papakea A108 NEW LISTING Remodeled OceanFront Papakea 1Bedroom with Panoramic Ocean Views for Front Row Sunsets and Year Round Indoor-Outdoor Living Escape to the tranquil beauty of West Maui with a stay in our beautifully furnished ground floor oceanfront 1-bedroom vacation rental at Papakea Resort. This remodeled gem offers a perfect blend of comfort and natural beauty, making it an ideal choice for your getaway. The moment you step inside, you'll be greeted by the soothing sounds of the ocean waves just steps away, and the tastefully decorated living space offers a cozy retreat with all the amenities you need for a relaxing vacation.

Check rates on Whimstay →

No. 285

Oceanfront Escape with Resort Amenities - Serene Tropical Sanctuary

Condo

1 bedroom sleeps 4 private pool about $183 a night

This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances. Oceanfront Escape with Private Lanai, Chef's Kitchen, and Resort Amenities Steps from the Beach Welcome to your puʻuhonua (sanctuary) in paradise, where Maui's serene oceanfront lifestyle becomes your reality. Picture yourself waking up to the sound of the nalu (waves) and stepping onto your private lanai to bask in breathtaking views of Lāna'i and Moloka'i. This is where relaxation and adventure meet, where every sunrise and sunset paints the sky with unforgettable colors just for you. Your condo is steps from the beach, nestled within 13 acres of lush ʻāina aloha (beloved land).

Check rates on Whimstay →

No. 286

Ocean Views and Two Pools - Stunning Oceanfront Haven

Condo

1 bedroom sleeps 4 private pool about $195 a night

Spacious Ground-Floor OceanFront Condo with Ocean Views, AC & Pool - Napili Point B5 Welcome to your Maui Retreat: Spend the day oceanside in the comfort of cool air all year long! This is a coveted oceanfront condo that is right on Napili Point. This one-bedroom, one-bathroom ground floor unit is the perfect place for your vacation. Napili Point B5 was remodeled in 2018 with updated furniture, flooring, split AC system, and a renovated kitchen equipped with all the countertop appliances you need for your stay.

Check rates on Whimstay →

No. 287

Oceanfront Lanai and Scenic Views - Stunning Hawaiian Retreat

Condo

1 bedroom sleeps 4 private pool about $194 a night

Welcome to your Maui Retreat: Dreaming of your next Maui getaway and looking for that perfect spot to relax and let your worries drift away? Kihei Surfside 306 offers just that; with amazing ocean breezes, ocean views and awe-inspiring beach walks. This convenient South Kihei location is steps from the beach and minutes away from all the activities and attractions of South Maui including the Makena and Wailea Resort areas. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences, plus unbeatable savings on other local favorites!

Check rates on Whimstay →

No. 288

Watch Sunsets Over the Ocean

Condo

1 bedroom sleeps 2 shared pool about $252 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 49C At 49C, the private lanai walks straight out to the tropical gardens, step outside and you're already there, the Pacific visible through the palms. A romantic ground-floor 1-bedroom condo meant for two, with a King bed and a walk-in shower. Keawakapu Beach is a short walk through the gardens, where sea turtles glide offshore year-round. Four resort pools, pickleball courts, and an oceanfront BBQ pavilion are close by. WHY OUR GUESTS LOVE IT. Sweeping Ocean Views: The private lanai at 49C frames a proper ocean outlook that earns its billing and sets the tone for your whole stay.

Check rates on Whimstay →

No. 289

Ocean View and Spacious Patio - Stunning Beachfront Escape

Condo

1 bedroom sleeps 4 private pool about $753 a night

Wailea Elua 1201 is perfectly positioned in the coveted interior courtyard, 39 steps to famous Ulua Beach, perennially named as one of the world's top 10 beaches and one of the best snorkeling reefs on Maui. This ground floor condo features an oversized, shaded patio/lanai, a perfect vantage point to keep an eye on the little ones on the beach and grassy area directly in front of the condo. Off your private lanai, you can be in the warm Maui waters in 30 seconds. Enjoy mesmerizing, spectacular ocean views from the spacious living room and beautifully updated kitchen, and enjoy the tropical breezes off the ocean when you are not chilling out with the central AC.

Check rates on Whimstay →

No. 290

Spacious Ground-Floor Condo and Expansive Lanai - Inviting Maui Retreat

Condo

2 bedroom sleeps 6 private pool about $602 a night

Experience the ultimate Maui getaway at Kaanapali Royal L101, a spacious ground-floor condo offering nearly 1,900 square feet of comfort and style. Perfect for families or groups, this beautiful two-bedroom, two-bathroom retreat comfortably accommodates up to six guests. Step out onto the expansive lanai, where you can savor outdoor dining with a large table that seats 6-7 people, a propane grill, and a dry sink for easy meal prep. The double lanai overlooks the lush fairways of the Kaanapali Golf Course, providing a tranquil setting to relax and unwind. Enjoy direct access to a beautifully manicured lawn and take advantage of the condo's proximity to the pool.

Check rates on Whimstay →

No. 291

Spacious Lanai and Modern Amenities - Stunning Oceanfront Villa

Condo

2 bedroom sleeps 6 about $438 a night

Enjoy the sounds of the waves and endless ocean views from this beautifully appointed two-bedroom Bay Villa, perfectly positioned right on the ocean. Bay Villas #25G2 2 Bedroom 3 Bath Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 25G2 has a large oceanfront patio off the living area with direct lawn access. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Master bedroom has 1 king bed. Second bedroom has 1 king bed.

Check rates on Whimstay →

No. 292

Coastal Sophistication and Chic Comfort - Exquisite Beachfront Retreat

Condo

2 bedroom sleeps 6 private pool about $213 a night

*. *. * Important Property Notice: Please be aware that there is active construction and a sinkhole repair zone located directly in front of the property. This may cause daytime noise and temporary changes to building access and travel routes. We appreciate your patience and flexibility as our community completes these necessary infrastructure repairs. *. *. Experience the best of South Kihei's beachfront lifestyle with Kihei Akahi D-515 - now under new ownership and new management, this renovated vacation rental is set to impress. With a comprehensive full renovation underway, every detail is being reimagined for modern comfort and island elegance.

Check rates on Whimstay →

No. 293

Oceanfront Swimming Pool and Jacuzzi - Charming Tropical Escape

Condo

2 bedroom sleeps 8 private pool about $294 a night

Enjoy being lulled to sleep by the sounds of the surf and the palm leaves swaying in the cool tropical breezes in this charming ocean front condo. Private lanai showcases a beautiful view that can be seen from the living room and kitchen. Also found here is an open air loft, with sleeping accommodations for up to four additional people. the property manager prides itself in providing you the best experience during your stay. As a thank you for staying with us you will receive one complimentary admission to popular local attractions every day.

Check rates on Whimstay →

No. 294

Hale Mahina B403

Vacation Rental

2 bedroom sleeps 4 private pool about $147 a night

Welcome to Hale Mahina B403. This beautifully remodeled top floor beachfront 2 bedroom, 2 bath condo boasts expansive ocean views & classic Hawaiiana decor. This condo features a remodeled kitchen with stainless appliances, office desk, & breathtaking views. Hale Mahina is a very special smaller resort as it's one of the only resorts in the Honokowaii with useable sandy beach. Located in close proximity to farmers market, food truck park, shops, beach, dining, & farmers market. Book today! WHY YOU’LL LOVE IT. Remodeled top-floor 2BR / 2BA beachfront condo (sleeps up to 6). Panoramic ocean views from nearly every room. Classic Hawaiiana décor with upgraded kitchen & finishes.

Check rates on Whimstay →

No. 295

Oceanfront Lanai and Stunning Views - Exquisite Tropical Sanctuary

Condo

2 bedroom sleeps 6 private pool about $156 a night

Welcome to your Maui Retreat: Sea turtles (“Honu”) routinely hang out on this seasonal beach directly in front of our condo, Hale Mahina B401. Enjoy the large, private lanai to watch sunsets where you will have unobstructed views of the neighboring islands. Spacious open living and kitchen area with views from galore. Beautiful 2 bedrooms and 2 bathrooms corner unit that sleeps up to 6 guests comfortably. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences, plus unbeatable savings on other local favorites!

Check rates on Whimstay →

No. 296

Ocean Front Escape and Stunning Sunsets - Charming Family Haven

Condo

2 bedroom sleeps 5 private pool about $184 a night

Welcome to Aloha Crush Maui, a true oceanfront escape at Maui Sands in beautiful West Maui. From your private lanai, enjoy uninterrupted Pacific views, seasonal whale watching, sea turtles in the surf, and unforgettable Hawaiian sunsets. This oceanfront condo places you just steps from the shoreline and offers access to a refreshing swimming pool, lush tropical landscaping, and a relaxed boutique-style setting that feels peaceful yet perfectly located. Spend your mornings with coffee overlooking the water, afternoons snorkeling at nearby beaches like Napili Bay and Kaanapali Beach, and evenings unwinding by the pool or listening to waves under the stars.

Check rates on Whimstay →

No. 297

Wailea Condo Great for Families

Condo

2 bedroom sleeps 6 shared pool about $320 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 20H This spacious 1,505 sq.ft. second-floor condo, offers captivating ocean views over tropical resort gardens from 3 private balconies. It's indoor-outdoor layout sleeps up to 6 comfortably and offers all the comforts of the home: from fully equipped kitchen to in-unit laundry. Take advantage of 4 resort pools, oceanfront pavilion at the thought-after Keawakapu Beach and easy walkable access to Wailea's best dining and shopping. WHY OUR GUESTS LOVE IT. Elevated Ocean Views: Relax on 3 separate balconies and take in lovely, elevated ocean views over the resort gardens.

Check rates on Whimstay →

No. 298

Stunning Ocean Views and Relaxing Amenities - Charming Oceanfront Haven

Condo

1 bedroom sleeps 4 private pool about $117 a night

Enjoy Unbeatable Ocean Views at this Adorable OceanFront Condo for Front Row Sunsets and Whale Watching - Maalaea Banyans 203 Welcome to Your Maui Retreat: Looking for an unbeatable ocean view in a quiet, relaxing location? Maalaea Banyans 203 is oceanfront, and has a great sandy beach within walking-distance. Enjoy the easy access to all the areas/activities the island has to offer!. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences, plus unbeatable savings on other local favorites!

Check rates on Whimstay →

No. 299

Oceanfront Studio with Pool and Daily Activities - Charming Island Sanctuary

Condo

1 bedroom sleeps 3 private pool about $86 a night

Royal Kahana 104 Spacious Oceanfront Studio with Pool in West Maui Only steps from the ocean on an incredible oceanfront resort on the west Maui coast. This studio makes a relaxing vacation for a couple or family of three. Enjoy your morning cup of coffee or enjoy fabulous sunsets while gazing out at the neighboring islands of Molokai & Lanai. This is the perfect island getaway, with a fully equipped kitchen, full bathroom (no tub) and washer/dryer, Royal Kahana 104 will have you enjoying all of the comforts of home while on your Maui vacation.

Check rates on Whimstay →

No. 300

Ocean Views and Tropical Living - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 private pool about $155 a night

Papakea #F108: Begin your day on your private lanai, where you will enjoy ocean views and taste-test locally brewed coffee. During the evening, delight in romantic sunsets and views towards neighboring islands Molokai and Lanai. You'll appreciate the stunning bamboo cabinets and Malibu gold granite countertops as you channel your inner MasterChef and prepare meals from your fully equipped kitchen. Stainless steel kitchen appliances include an oven/stove, refrigerator, dishwasher, disposal, microwave, and toaster. Ceiling fans will circulate the Pacific breeze in your tropical-themed living room decorated in neutral colors.

Check rates on Whimstay →

No. 301

Wailea Ekahi 17B - Professionally Managed

Condo

1 bedroom sleeps 4 shared pool about $243 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 17B A spacious 1,000-sq.ft. 1-bedroom condo with 2 full bathrooms, offering step-free ground-floor walkout access and an extra large covered lanai. Enjoy distant ocean views over 34 acres of tropical gardens, 4 resort pools, and an 8-minute walk down shaded paths to Keawakapu Beach along lush resort grounds. Perfect for families, sleeping 4 with a king bed, double sleeper sofa, and beach essentials like wagon and chairs provided. WHY OUR GUESTS LOVE IT. Elevated Ocean Views: The exceptionally large private lanai offers beautiful, distant views of the ocean and neighboring islands.

Check rates on Whimstay →

No. 302

Expansive Lanai and Chef’s Kitchen - Stunning Oceanfront Villa

Condo

2 bedroom sleeps 6 about $463 a night

This stunning two-bedroom Bay Villa offers panoramic oceanfront views and a prime location closest to the ocean, ideal for a serene and relaxing Maui getaway. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 19G2 has a large oceanfront patio with direct lawn access. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Master bedroom has 1 king bed. Second bedroom has 1 king bed. Master bathroom with a free-standing shower.

Check rates on Whimstay →

No. 303

Ocean View and Rooftop BBQ - Gorgeous Beachfront Oasis

Condo

2 bedroom sleeps 6 private pool about $150 a night

Remodeled 2Bedroom BeachFront Condo with Ocean Views, Split AC, Pool, Rooftop BBQ. Idyllic Winter Family Getaway - Menehune Shores 403 Welcome to Your Maui Retreat: Menehune Shores 403 is the perfect spot for your next Maui family vacation. Beautifully remodeled and updated with modern furnishings and decor, our Maui condo offers all the comforts of home with wonderful ocean, beach and sunset views and plenty of space for your entire family to enjoy. With easy elevator access to the tropical grounds, beach, pool, BBQs and other resort amenities you'll have to make amazing Maui memories.

Check rates on Whimstay →

No. 304

Beachfront & Modern. Makena Surf A102

Condo

2 bedroom sleeps 6 private pool about $714 a night

Welcome to the Makena Surf A102 Beachfront Resort, your perfect oasis in Wailea, HI. This stunning 2-bedroom, 2-bathroom oceanfront condo sleeps up to six guests and offers a luxurious retreat with breathtaking views of the Pacific Ocean. Step inside to find a spacious, open-concept living area with a fully equipped kitchen, perfect for preparing meals while enjoying the ocean breeze. The living room features a cozy seating area with a flat-screen TV, ideal for relaxing after a day of exploration. The master bedroom boasts a king-sized bed, en-suite bathroom with a bathtub, and direct access to the private balcony, where you can sip your morning coffee while watching the sunrise.

Check rates on Whimstay →

No. 305

Spacious Lanai and Modern Kitchen - Exquisite Oceanfront Haven

Condo

1 bedroom sleeps 4 about $351 a night

Enjoy the best of both worlds in this spacious oceanfront Bay Villa featuring one bedroom plus a versatile bonus bedroom. It offers stunning ocean views, comfortable living spaces, and the perfect setup for families or groups seeking a relaxed Maui getaway. Bay Villas #27G3 1 Bedroom 2 Bath + Bonus Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 27G3 is 2 levels with a unique bonus bedroom and views of the ocean and the island of Molokai. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware.

Check rates on Whimstay →

No. 306

Oceanfront Lanai and Breathtaking Sunset Views - Exquisite Maui Retreat

Condo

2 bedroom sleeps 4 private pool about $146 a night

Welcome to your Maui Retreat: At Waiohuli Beach Hale, the ocean is your backyard! This 2-bedroom, 2-bathroom condo is located in South Kihei, steps from a long stretch of golden sand, perfect for sunset strolls or dipping your toes in the water. The outdoor lanai is where most days seem to begin and end, enjoy ocean views and a front-row seat to the fiery sky as the sun slides behind the neighboring island of Lanai. Inside, the condo feels comfortable and easygoing. The primary bedroom offers peace and privacy with its own ensuite bathroom, while the second bedroom is perfect for family or friends traveling together.

Check rates on Whimstay →

No. 307

Luxury Oceanfront Mana Kai Resort Condo

Entire condo

2 bedroom sleeps 4 private pool about $667 a night

Plan your ideal Hawaiian escape and book a stay at this 2-bedroom, 2-bath vacation rental located in Mana Kai Maui Resort. Nestled on the shores of Keawakapu Beach, this ocean-front condo provides luxury furnishings, panoramic ocean and pool views throughout it’s interior space, and everything you’ll need for an unforgettable getaway. Spend your days lounging by the pool, snorkeling in the crystal blue waters, teeing off at local golf courses, or perusing The Shops at Wailea! The space TA-099-0958-6304-01. GE-099-0958-6304-01. Keyless Entry.

Check rates on Whimstay →

No. 308

Oceanfront Lanai and Breathtaking Views - Relaxing Maui Retreat

Condo

2 bedroom sleeps 4 shared pool about $193 a night

FLASH SUMMER SALE! We're offering exclusive discounts on all summer stays booked this week, don't miss out on these updated lower rates. Welcome to your Maui Retreat: This 2-bedroom, 2-bathroom oceanfront condo at Lauloa Resort offers the kind of Maui stay that's both relaxing and convenient. Set right on Maalaea Bay, the condo features a spacious furnished lanai where you can take in sweeping views of the ocean, the resort pool below, and even Molokini crater in the distance. Whether you're enjoying your morning coffee or winding down at sunset, this outdoor space is likely where you'll spend much of your time.

Check rates on Whimstay →

No. 309

Oceanfront Lanais and Panoramic Views - Luxurious Coastal Retreat

Condo

2 bedroom sleeps 6 about $676 a night

Indulge in luxury in this newly renovated condo, offering 1,287 sq ft of living space and breathtaking wrap-around lanais. Located in a premier beachfront spot between Kaanapali and Kapalua. The expansive living and dining area, seating up to six, showcases panoramic ocean views through expansive windows. Relax in the oceanfront master bedroom with a king bed and private bath, or enjoy the guest bedroom with its own king bed and bath. Additional amenities include a fully equipped kitchen, spacious living room with flat screen TV and free WiFi, queen sleeper sofa, central AC, washer/dryer, and complimentary daily admissions to local attractions. Your dream Maui vacation awaits!

Check rates on Whimstay →

No. 310

Makena Surf A204 Beachfront Resort

Condo

2 bedroom sleeps 6 shared pool about $552 a night

CORALTREE RESIDENCE COLLECTION presents. Makena Surf A204 Experience an intimate Hawaiian retreat at this 2-bedroom second-floor condo on Po'olenalena Beach. Perfect for families or couples, this quiet escape offers spectacular ocean, mountain, and pool views on three sides. Enjoy instant access to a secluded stretch of sand, world-class sea turtle snorkeling directly in front of the property, and 32 acres of lush tropical gardens. WHY OUR GUESTS LOVE IT. Unmatched 3-Sided Views: Guests rave about the unique vantage point from this second-floor unit, offering sweeping views of the ocean, mountains, and resort pool.

Check rates on Whimstay →

No. 311

Recently Renovated at Wailea Beach Villas

Condo

2 bedroom sleeps 6 private pool about $1180 a night

Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of your delight. Open up your lanai doors and head outside to look for whales or watch the snorkel boats heading to Molokini Crater. This two-bedroom, two-bathroom Maui retreat will comfortably accommodate families or friend groups while optimizing space, privacy and comfort for all guests. The open floorplan blends the living room, dining room, and kitchen into one great room perfect for socializing with your traveling companions.

Check rates on Whimstay →

No. 312

Oceanfront Studio with Lanai, Sunset & Island Views - Lahaina Shores 515

Condo

1 bedroom sleeps 2 private pool about $112 a night

Breathtaking Ocean and Sunset Views from this Beautifully Remodeled Studio Condo Just an Elevator Ride from the Beach, Pool and Hot Tub - Lahaina Shores 515 Welcome to your Maui Retreat: Wake up to the soothing sounds of the ocean at Lahaina Shores 515, a remodeled 5th floor studio right on the beach. Enjoy your morning coffee on the private lanai while looking out at the turquoise water and the neighbor islands of Lāna'i and Moloka'i. This bright, updated space features a full bathroom, and a modern kitchen with a handy breakfast bar for meals on the go, plus a small dining table for two. At night, relax in the comfortable king bed and fall asleep to the gentle sounds of the waves.

Check rates on Whimstay →

No. 313

Remodeled BeachFront 2BD Whale Watching-Menehune Shores 402

Condo

2 bedroom sleeps 6 private pool about $158 a night

Come and Enjoy South Maui from this Remodeled Kihei Condo on the Beach with Ocean Views Steps from the Sand-Menehune Shores 402 Welcome to Your Maui Retreat: Experience stunning ocean views, direct beach access, and remodeled interiors at this updated 2-bedroom Kihei condo. With split AC throughout, brand-new furnishings, and a prime North Kihei location close to world-class beaches, snorkeling, Maui attractions, and dining, this home is the ideal destination for your next island getaway.

Check rates on Whimstay →

No. 314

Beachfront Kihei Sanctuary w/ Lanai & Ocean Views!

Entire condo

2 bedroom sleeps 6 private pool about $277 a night

Let this alluring beachfront Kihei vacation rental serve as your own personal oasis in beautiful Maui! With 2 bedrooms, 2 bathrooms, a private lanai, and sensational ocean views, this condo leaves nothing to be desired. Wake up early to catch the morning surfing waves, plan snorkeling adventures during the day, and attend a luau by night for some local fare and entertainment. If you prefer to stay on-site, take advantage of the amazing community amenities and sunbathe by the pool all day long! The space License #: GE- -01. License #: TA - -01. Furnished Balcony. On-Site Beach Access.

Check rates on Whimstay →

No. 315

Oceanfront Polo Beach 407 - Professionally Managed

Condo

2 bedroom sleeps 6 private pool about $556 a night

Welcome to the Polo Beach Club 407, your perfect oasis in Wailea, Hawaii. This stunning two-bedroom, oceanfront condo offers a luxurious retreat for up to six guests. Step inside to find a spacious, open-concept living area with a cozy sofa bed, perfect for unwinding after a day at the beach. The master bedroom features a plush king bed, while the second bedroom offers two comfortable double beds, ensuring a restful night's sleep for everyone. Both bathrooms are fully equipped with modern amenities, providing convenience and comfort. The fully-stocked kitchen includes everything you need for a home-cooked meal, and the dining area overlooks the serene ocean view.

Check rates on Whimstay →

No. 316

Direct Ocean Views and Beach Access - Stunning Oceanfront Retreat

Condo

2 bedroom sleeps 6 private pool about $256 a night

This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances. Mahana 1111 - Your Oceanfront Paradise on Kaanapali Beach Welcome to your stunning, direct oceanfront 2-bedroom, 2-bathroom luxury condominium located on the pristine Kaanapali Beach. This upgraded retreat offers breathtaking panoramic views of the Pacific Ocean and neighboring islands, ensuring your Maui vacation is unforgettable. Key Features of Your Oceanfront Retreat: Spacious Layout: Enjoy a beautifully designed space that offers plenty of room for relaxation and gathering with family or friends.

Check rates on Whimstay →

No. 317

Spacious Lanai and Gourmet Kitchen - Stunning Oceanfront Loft

Condo

2 bedroom sleeps 6 about $429 a night

Nestled directly on the ocean, this two-bedroom Bay Villa boasts incredible ocean views and spacious living areas, making it the perfect coastal retreat in Kapalua Resort. Bay Villas #27B2 2 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 27B2 is a split-level loft style villa with a large oceanfront patio off the living area. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent.

Check rates on Whimstay →

No. 318

Wailea Beach Villas PH306

Condo

2 bedroom sleeps 6 private pool about $1135 a night

Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed with cool turquoise and cinnamon accents, original Hawaiian artwork, and modern finishes, this vacation residence is perfect for a family or two couples. The open floorplan gracefully extends to the outdoor lanai through sliding doors, securing an added layer of ambiance and flow to your stay. Catch the game or a movie from the 60” HDTV in your spacious living room.

Check rates on Whimstay →

No. 319

Direct Access to Pool and BBQs - Charming Oceanfront Retreat

Condo

1 bedroom sleeps 4 private pool about $100 a night

Located ground floor and on the oceanfront in Kahana, this 1-bedroom/1-bath fully equipped condo has all you will want and need for the quiet Maui vacation. A portable A/C unit was recently installed in the living room. Walk right out to the oceanfront pool, BBQs, and a sea wall and enjoy the cool West Maui trade winds. Guests will enjoy watching sunsets year-round and whales in the winter. Walk into Kahana for shopping and dining or 5 minutes in either direction to white sandy beaches. Nearby Beaches to Kahana Reef: 1. Kahekili Beach Park (Airport Beach): Generally calm conditions, excellent snorkeling and swimming, public restrooms, BBQ grills, and a large grassy area. 2.

Check rates on Whimstay →

No. 320

Oceanfront Lanai and Pool - Stunning Tropical Escape

Condo

2 bedroom sleeps 6 private pool about $146 a night

Welcome to your Maui Retreat: Enjoy this recently remodeled 2bedroom oceanfront condo with a sprawling ocean view and lookout to the islands of Molokai and Lanai in the distance. Kulakane 306 is perfect for a large family or group of friends, this home has an oceanfront covered lanai for indoor-outdoor living. Complimentary Activities, Every Day of Your Stay Every reservation with includes one free ticket per activity, each day to some of our favorite Maui experiences plus unbeatable savings on other local favorites! This exclusive benefit is offered in partnership with Xplorie, giving you an easy way to add adventure, relaxation, and local flavor to your stay.

Check rates on Whimstay →

No. 321

SUMMER SALE! Remodeled Oceanfront 2-bedroom Condo See Turtles & Whales - NP C15

Apartment

2 bedroom sleeps 6 private pool about $296 a night

Napili Point C15 Breathtaking Direct Oceanfront Views from Napili and Honokeana Cove, Watch Turtles and Whales from the Lanai Welcome to your Maui Retreat: This two-story oceanfront condo at Napili Point, Unit C15, offers a front-row seat to the natural beauty that makes West Maui so special. From the moment you step inside the views pull you in, with wide open ocean, rugged coastline, and neighboring islands off in the distance. It's a bright, spacious retreat with a relaxed feel, perfect for travelers who want to unwind in a setting that feels close to nature yet comfortably updated.

Check rates on Whimstay →

No. 322

Spacious Villa with Modern Amenities - Spectacular Coastal Retreat

Condo

1 bedroom sleeps 4 about $311 a night

Experience Maui’s finest coastal living in this oceanfront one-bedroom Bay Villa, featuring nearby beach access and stunning views of the sparkling Pacific Ocean. Bay Villas #36B3 1 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 36B3 is split-level and overlooks the Pacific Ocean, a bird sanctuary and the island of Molokai. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Bedroom has 1 king bed.

Check rates on Whimstay →

No. 323

Oceanfront Escape with Panoramic Views - Stunning Island Retreat

Condo

1 bedroom sleeps 2 private pool about $112 a night

NEW LISTING Experience Your Next Maui Oceanfront Escape in this Studio with Sweeping Views of the Pacific! - Lahaina Shores 413 Welcome to your Maui Retreat: Located directly on the beach, this Island retreat features unobstructed views of the Pacific Ocean and the neighboring islands of Lanai and Molokai and overlooks the resort's sparkling pool and hot tub. Step out onto your private furnished lanai to take in breathtaking sunsets, watch the waves roll in, and feel the gentle island breeze. Inside, a cozy King bed offers the perfect place to rest after a day of island adventures, while the open layout creates a light and airy atmosphere.

Check rates on Whimstay →

No. 324

Ocean View and Swimming Pool Access - Elegant Oceanfront Haven

Condo

1 bedroom sleeps 4 private pool about $264 a night

Wake up to breathtaking ocean views in this cozy one-bedroom unit near beaches and ideal for families, romantic couples, or solo travelers. Unit 615 Ocean View 1 Bedroom 1 Bath. 6th floor condo with nice views of ocean and the island of Molokai. Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, toaster, blender, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, tea, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Bedroom has 1 king bed. Bathroom with free-standing shower. Bath amenities include shampoo/conditioner, soap, lotion & hair dryer. Dining room table with seating for 4.

Check rates on Whimstay →

No. 325

Kahana Reef 215

Condo

1 bedroom sleeps 4 private pool about $289 a night

Your Oceanfront Escape Begins at Kahana Reef 215 Step into paradise the moment you arrive. Kahana Reef 215 sits directly on the water’s edge, so close you’ll fall asleep to the lull of the waves and wake to stunning, unobstructed ocean views. Enjoy your morning coffee or a sunset cocktail on the private, furnished lanai as the sky paints itself in colors over Lanai and Molokai. During whale season, the magic unfolds right in front of you. Inside, this beautifully updated condo blends island charm with modern comfort. The fully equipped kitchen features granite countertops and sleek appliances, perfect for preparing meals to enjoy indoors or alfresco.

Check rates on Whimstay →

No. 326

Balcony and Open Kitchen with BBQ Grills - Stylish Coastal Retreat

Condo

1 bedroom sleeps 4 about $308 a night

This oceanfront one-bedroom offers direct access to Maui’s pristine beaches, perfect for couples, small groups, or travelers craving relaxation by the sea. Unit 208 Oceanfront 1 Bedroom 1 Bath. 2nd floor condo with oceanfront views and views of the island of Molokai. Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, toaster, blender, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, tea, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Bedroom has 1 king bed. Bathroom with free-standing shower. Bath amenities include shampoo/conditioner, soap, lotion & hair dryer. Dining room table with seating for 4.

Check rates on Whimstay →

No. 327

Wailea Ekahi Village 7A

Condo

1 bedroom sleeps 4 shared pool about $263 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 7A A spacious 1,090 sq.ft. 1-bedroom ground-floor condo offering step-free access and a private tropical garden view lanai with BBQ. Located just steps from resort pool and an easy 2-minute walk to the newly renovated oceanfront pavilion and reknown Keawakapu Beach. Perfect for families, sleeping up to 4 with resort perks like pickleball, Wailea shopping and dining within easy walking distance, and world-class golfing nearby. WHY OUR GUESTS LOVE IT. Outstanding Beach Proximity: Enjoy an exceptionally short 2-minute stroll down gentle garden pathways straight to the sand of Keawakapu Beach. Spacious 1,090 sq.ft.

Check rates on Whimstay →

No. 328

Top-Floor Elegance and Premium Amenities - Stunning Retreat

Condo

1 bedroom sleeps 4 private pool about $309 a night

At Wailea Ekahi Village 20G, you and your guests will enjoy premier accommodations, furnishings and holiday experiences at this top-floor Wailea Ekahi vacation home. New paint, carpet, air-conditioning, and electronics, plus next-level furnishings and personal touches make this vacation condominium is perfect for your Wailea getaway. You are only steps away from world-famous Keawakapu Beach, pickleball courts and a select pool just for your section of Ekahi Village. Just around the corner is the Wailea Ekahi beachfront pavilion with the main pool and shuffleboard courts. Be sure to take a look at our virtual tour of the condo and the Ekahi property!

Check rates on Whimstay →

No. 329

Expansive Balcony and Luxurious Amenities - Stunning Oceanfront Retreat

Condo

2 bedroom sleeps 6 about $475 a night

This oceanfront two-bedroom unit provides a serene setting with spectacular ocean views. Great for groups, families, or couples looking to enjoy Maui’s coastal beauty. Unit 310 Oceanfront 2 Bedroom 2.5 Bath. 3rd floor condo with large wraparound balcony with views of ocean and the islands of Lanai and Molokai. Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, toaster, blender, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, tea, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Master bedroom has 1 king bed and ensuite bathroom. Second bedroom has 1 double bed and 1 twin bed.

Check rates on Whimstay →

No. 330

Spacious Lanai and Modern Kitchen - Stunning Oceanfront Haven

Condo

1 bedroom sleeps 4 about $306 a night

Wake up to the ocean breeze and sparkling waves in this beachfront one-bedroom Bay Villa, perfectly situated for easy access to Kapalua’s pristine Oneloa Beach. Bay Villas #19G4 1 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 19G4 is a short walk to Oneloa Beach via the Kapalua Coastal Trail. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Bedroom has 1 king bed. Bathroom with a free-standing shower and soaking tub.

Check rates on Whimstay →

No. 331

Oceanfront Studio on the Beach with Lanai & Stunning Island Views - Lahaina Shores 517

Condo

1 bedroom sleeps 2 private pool about $112 a night

Stunning Beachfront Views from this Beautifully Updated West Maui Studio Elevator Ride to the Beach, Pool and Jacuzzi - Lahaina Shores 517 Welcome to your Maui Retreat: Wake up to the calming sound of waves and unforgettable ocean views at Lahaina Shores 517, a beautifully remodeled oceanfront studio located right on the beach. Enjoy your morning coffee on the private lanai while watching the turquoise water and neighboring islands of Lāna'i and Moloka'i shimmer in the distance. Inside, you'll find a fully equipped kitchen with a convenient breakfast bar, or you can dine at the intimate table for two with the ocean as your backdrop.

Check rates on Whimstay →

No. 332

Oceanfront Retreat with Panoramic Views & Beachfront Lanai -Mahana

Condo

2 bedroom sleeps 6 private pool about $282 a night

Direct Oceanfront 2 Bedroom Condo with Bright Interiors and Panoramic Ocean Views - Mahana 109 Welcome to your Maui Retreat: Located just steps from the shoreline, this bright and airy 2-bedroom, 2-bathroom condo features floor-to-ceiling windows that perfectly frame panoramic views of the Pacific Ocean and neighboring islands. The open-concept living area flows effortlessly onto a private lanai, making it easy to enjoy your morning coffee with the sound of the waves or unwind while watching the sunset over the Pacific.

Check rates on Whimstay →

No. 333

Oceanfront Lanai and Gourmet Kitchen Retreat - Elegant Oasis

Condo

2 bedroom sleeps 6 about $448 a night

Wake up to breathtaking ocean vistas in this inviting two-bedroom Bay Villa, where coastal beauty meets comfort and style. Bay Villas #19B2 2 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 19B2 is a single level with ocean views from every room. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Master bedroom has 1 king bed. Second bedroom has 2 twin beds. Master bathroom with a shower/tub combination.

Check rates on Whimstay →

No. 334

Spacious Lanai and Chef’s Kitchen - Stunning Oceanfront Retreat

Condo

2 bedroom sleeps 4 about $573 a night

Experience unmatched oceanfront living in this spacious two-bedroom Bay Villa, just steps from the beach with sweeping views of the Pacific. Perfect for families or groups seeking a luxurious Maui escape. Bay Villas #18B2 2 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 18B2 is split-level with views from almost every window. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Master bedroom is loft style with 1 king bed.

Check rates on Whimstay →

No. 335

Direct Oceanfront 2BR with Spectacular Sunset Views -Kamaole Nalu 604

Condo

2 bedroom sleeps 4 private pool about $156 a night

Spectacular Ocean and Beach Views and from this Direct Oceanfront 2 Bedroom South Maui Condo - Kamaole Nalu 604 Welcome to your Maui Retreat: Welcome to Kamaole Nalu 604, a remodeled 2-bedroom, 2-bathroom oceanfront condo in the heart of Kihei, South Maui. Perched directly above the shoreline, this South Maui retreat offers spectacular ocean views, unforgettable sunsets, and the soothing sound of the waves just outside your doors.

Check rates on Whimstay →

No. 336

SUMMER SALE! Experience Oceanfront luxury in West Maui! - Polynesian Shores 224

Condo

2 bedroom sleeps 6 private pool about $135 a night

Welcome to Your Maui Retreat: This 2-bedroom, 2-bathroom second-floor condo at the Polynesian Shores Oceanfront Condominiums offers relaxing ocean views overlooking the swimming pool, hot tub, and the resort's lush tropical lawn and gardens. The spacious furnished lanai is a great place to start the day with coffee or wind down in the evening while enjoying the sound of the ocean. Inside, the condo has an open and airy floor plan with comfortable living and dining spaces that connect easily to the outdoor lanai. The fully equipped remodeled kitchen provides everything needed for preparing meals during your stay.

Check rates on Whimstay →

No. 337

2 Ensuites. Top Floor Oceanfront. Big Lanai. Work Station w. View

Condo

2 bedroom sleeps 6 about $328 a night

Guests must sign rental terms. $500 deposit held for damages, released 3 days post-checkout. Strictly non-smoking. EXHIBIT A - RENTAL RULES Throughout the Rental Period, the Guest shall, and shall ensure that the Rental Party and any visitors (collectively “Occupants”) to the Rental Unit shall abide by the following rules: 1. No occupant shall make or allow any disturbing noise in the buildings or on the premises, nor do or permit anything to be done that will interfere with the rights, comfort and convenience of others. All occupants are to refrain from the blowing of conch shells at any time other than at sunset each evening for a five-minute duration only. 2.

Check rates on Whimstay →

No. 338

Direct Oceanfront Corner 2BR with Panoramic Views -Sands of Kahana 243

Condo

2 bedroom sleeps 6 private pool about $360 a night

Enjoy Breathtaking Direct Oceanfront Views from Every Window of this Spacious West Maui Condo, Beach, Pool, Jacuzzi, Onsite Restaurant and Bar. Sands of Kahana 243 Welcome to Your Maui Retreat: This beautifully remodeled direct oceanfront corner condo at Sands of Kahana Resort offers an expansive 1,660 sq. ft. of comfortable indoor-outdoor living in one of West Maui's most desirable locations. The open-concept main living space is bright and inviting, with large windows that frame stunning ocean views and fill the condo with natural light.

Check rates on Whimstay →

No. 339

Recently Renovated - Oceanfront in Makena

Condo

2 bedroom sleeps 6 shared pool about $602 a night

CORALTREE RESIDENCE COLLECTION presents. Makena Surf B201 Experience an intimate Hawaiian retreat at this 2-bedroom second-floor condo on Po'olenalena Beach. Perfect for families, this quiet escape offers spectacular ocean views with direct balcony access from both bedrooms. Enjoy world-class sea turtle snorkeling right off the property, 32 acres of lush tropical gardens, and resort pools and a shared hot tub right at your fingertips. WHY OUR GUESTS LOVE IT. Balcony Access for All: Both the primary and second bedrooms offer direct balcony access with stunning ocean views. Nature's Front Row: Enjoy world-class snorkeling with sea turtles every day right off the property's shoreline.

Check rates on Whimstay →

No. 340

Makena Surf G203. Serene Oceanfront Hideaway

Condo

2 bedroom sleeps 6 shared pool about $607 a night

CORALTREE RESIDENCE COLLECTION presents. Makena Surf G203 Immerse yourself in tranquility at this secluded 2-bedroom, second-floor sanctuary overlooking Po'olenalena Beach. Tucked into one of the most private and quiet corners of the 32-acre botanical estate, this retreat provides elevated panoramic views of the Pacific, perfect for seasonal whale watching. Our guests love the incredibly peaceful atmosphere, world-class sea turtle snorkeling, and having a resort pool and shared hot tub right at their fingertips. WHY OUR GUESTS LOVE IT.

Check rates on Whimstay →

No. 341

Makena Surf B305 Beachfront Resort

Condo

2 bedroom sleeps 4 private pool about $627 a night

Welcome to Makena Surf B305, an extraordinary oceanfront retreat offering some of the most breathtaking views on all of Maui. Perfectly positioned within the exclusive gated Makena Surf resort, this spacious two-bedroom, two-bathroom residence sits just steps from the some of the best snorkeling on Maui. Snorkel boat tours often anchor just offshore. From the instant you walk through the front door, you’re greeted by sweeping panoramic ocean views, the sound of gentle waves below, and the feeling of complete island serenity. Floor-to-ceiling sliding door help blend the indoor living space with the oversized lanai and creates the true indoor-outdoor lifestyle Hawaii is known for.

Check rates on Whimstay →

No. 342

Hear the Waves Crash - Oceanfront

Condo

2 bedroom sleeps 6 private pool about $920 a night

Welcome to the serene and luxurious Wailea Elua Village 1703, a stunning 2-bedroom oceanfront condo nestled in the heart of Wailea. This meticulously designed property offers a perfect blend of comfort and elegance, making it an ideal retreat for your next Hawaiian getaway. Step inside to discover a spacious, open-concept living area that seamlessly flows into a private balcony, offering breathtaking views of the ocean. The living room features a cozy sofa bed, perfect for additional guests, while the fully equipped kitchen includes modern appliances, a coffee maker, and all the essentials for a comfortable stay.

Check rates on Whimstay →

No. 343

Wailea Beach Villas PH210

Condo

2 bedroom sleeps 6 private pool about $1109 a night

Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish overstuffed Tommy Bahama furniture in a soothing color palette of caramel, cherry, and sage green. The open living area is bathed in natural light, showcasing both garden and partial ocean views, making it a perfect environment for relaxation and family gatherings. For entertainment, the penthouse is equipped with three large flat-screen HDTVs, ensuring that guests can enjoy a variety of viewing options.

Check rates on Whimstay →

No. 344

Wailea Beach Villas PH502 - Professionally Managed

Condo

2 bedroom sleeps 6 private pool about $1248 a night

Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual decor. Your private elevator landing on the top floor offers a glimpse of the dramatic and towering Haleakala - south Maui’s majestic backdrop. Once inside, a wall of windows and sliding glass doors in the open living area fills your view with the relaxing blue hues of the Pacific Ocean.

Check rates on Whimstay →

No. 345

Ocean Views and Luxurious Amenities - Spacious Oceanfront Haven

Condo

1 bedroom sleeps 4 private pool about $126 a night

Spacious Studio at a Beautiful Oceanfront Resort in North Kaanapali. Unplug, Relax, and Recharge with Pools, Hot Tubs, Restaurants, and White Sand Beach - Kaanapali Shores 836 Welcome to your Maui Retreat: Wake up to soothing ocean views and the easy rhythm of island living at Kaanapali Shores 836, a spacious studio set within a beautifully maintained oceanfront resort in West Maui. From your private furnished lanai, enjoy gentle sea breezes while working comfortably with high-speed internet, then step away to soak in year-round sunshine, sandy beaches, and scenic walking trails just moments away.

Check rates on Whimstay →

No. 346

Beachfront Cabana and Resort Pools - Charming Hawaiian Getaway

Condo

1 bedroom sleeps 4 shared pool about $131 a night

Charming Maui Getaway at Updated 1Bedroom Condo at Maui Eldorado Resort in Kaanapali! Facilities include Pool, Hot Tub, Fitness Room and Beachfront Cabana - Eldorado L202 Professionally managed. Welcome to your Maui Retreat: Indulge in the ultimate Hawaiian escape at this updated 1-bedroom, 2-bathroom condo nestled within the serene Maui Eldorado Resort, along the pristine shores of Kaanapali Beach. The bright and airy interior of L202 is complemented by charming Hawaiian coastal decor that creates a peaceful and comfortable space to enjoy your time on the Valley Isle.

Check rates on Whimstay →

No. 347

Elegant Kitchen and Expansive Lanai - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 about $317 a night

This one-bedroom Bay Villa boasts prime oceanfront living with floor-to-ceiling views and nearby access to the beach, ideal for soaking up Maui’s coastal beauty. Bay Villas #19G5 1 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 19G5 is a split-level villa with views of the ocean and the island of Molokai. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Bedroom has 1 king bed.

Check rates on Whimstay →

No. 348

Expansive Lanai and Luxurious Kitchen Amenities - Stunning Coastal Oasis

Condo

1 bedroom sleeps 4 about $452 a night

Feel the ocean breeze and hear the waves from this stunning one-bedroom Bay Villa, perfectly positioned right on the beach for an authentic Maui oceanfront experience. Bay Villas #36B4 1 Bedroom Gold Oceanfront. The Bay Villas are located closest to 2 Kapalua Beaches - Oneloa Beach and Kapalua Beach. Villa 36B4 is one-level with easy access to both Kapalua and Oneloa beaches. Kitchen includes microwave, stovetop/oven, drip coffee maker, refrigerator, dishwasher, cookware and tableware. Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent. Bedroom has 1 king bed. Bathroom with a free-standing shower.

Check rates on Whimstay →

No. 349

Kihei Bay Vista C-201

Condo

1 bedroom sleeps 2 private pool about $153 a night

Kihei Bay Vista C-201 is a beautifully updated one bedroom, one bathroom condo designed for a relaxing and comfortable Maui stay. This second floor unit features a bright and airy layout with air conditioning and thoughtful touches throughout, making it ideal for couples or small groups of up to four guests. The bedroom offers a comfortable queen size bed, while the living area provides additional sleeping space, creating a welcoming retreat after a day of exploring the island. Inside, the condo is fully furnished with everything you need for a seamless vacation experience.

Check rates on Whimstay →

No. 350

SUMMER SALE! Updated Studio at Lahaina Shores Resort Near Beach & Pool - LS 212

Condo

1 bedroom sleeps 2 private pool about $96 a night

Welcome to your Maui Retreat: This updated second-floor studio at Lahaina Shores Beachfront Resort offers a relaxed and comfortable place to settle in while enjoying the beauty of West Maui, and just an elevator ride away from the oceanfront pool, jacuzzi, and beach access. From the furnished private lanai, take in peaceful views of the West Maui Mountains, where lush greenery and changing light create a scenic backdrop throughout the day. The condo has been remodeled with a fresh, clean feel that's both welcoming and practical for a laid-back island stay.

Check rates on Whimstay →

No. 351

SUMMER SALE! Remodeled Wonderful West Maui Mountain View in Oceanfront Resort - Lahaina Shores 620

Condo

1 bedroom sleeps 2 private pool about $96 a night

Beautifully Remodeled West Maui Mountain View Studio in a Beachfront Resort, Just an Elevator Ride to the Beach, Pool, and Hot Tub. Lahaina Shores 620 Welcome to Your Maui Retreat: Enjoy a relaxing stay in this beautifully remodeled 6th-floor mountain view studio at Lahaina Shores Beach Resort in West Maui. While the unit overlooks the lush West Maui Mountains, you're still part of a true oceanfront property, just an easy elevator ride brings you down to the beachfront pool, hot tub, and direct ocean access.

Check rates on Whimstay →

No. 352

SUMMER SALE! Mountain View Studio at Beachfront Resort in West Maui -Lahaina Shores 320

Condo

1 bedroom sleeps 2 private pool about $96 a night

Lahaina Shores 320 Remodeled West Maui Mountain View Studio in Breathtaking Beachfront Resort Minutes from Kaanapali, Napili and Kapalua Welcome to Your Maui Retreat: Enjoy a comfortable stay in this remodeled third-floor studio at Lahaina Shores Beachfront Resort, offering peaceful views of the West Maui Mountains. This bright and thoughtfully updated space features an open layout with a fully equipped kitchen, a full bathroom, and a comfortable living and sleeping area designed for a relaxing island stay.

Check rates on Whimstay →

No. 353

SUMMER SALE! Direct Oceanfront Studio with Lanai & Sunset Views -Lahaina Shores 631

Condo

1 bedroom sleeps 2 private pool about $112 a night

Breathtaking Direct Beachfront Views from this Remodeled West Maui Studio, Elevator Ride to the Beach, Pool, and Hot Tub Welcome to Your Maui Retreat: Wake up to the sound of the ocean and sweeping, unobstructed views from this cozy, remodeled 6th-floor direct oceanfront studio at Lahaina Shores Beachfront Resort. The private lanai is the perfect place to start or end your day, with panoramic beachfront scenery and the neighboring islands of Lanai and Molokai visible on the horizon. Inside, the space feels bright and open, thoughtfully designed to maximize comfort while keeping the focus on the incredible setting just beyond your windows.

Check rates on Whimstay →

No. 354

Direct Oceanfront Studio with Lanai & Sunset Views -Lahaina Shores 509

Condo

1 bedroom sleeps 2 private pool about $112 a night

Enjoy Breathtaking Direct Beachfront Views from this Remodeled West Maui Studio, Just Steps to the Beach, Hot Tub, and Pool. Lahaina Shores 509 Welcome to Your Maui Retreat: Enjoy the beauty of West Maui from this remodeled 5th-floor direct oceanfront studio at Lahaina Shores Beachfront Resort. Bright and welcoming, this comfortable condo offers stunning beachfront views from the moment you walk in. Step out onto the furnished private lanai and take in sweeping sights of the Pacific, with the neighboring islands of Lanai and Molokai visible in the distance.

Check rates on Whimstay →

No. 355

Direct Oceanfront Studio with Lanai & Sunset Views -Lahaina Shores 331

Condo

1 bedroom sleeps 2 private pool about $112 a night

Breathtaking Direct Beachfront Views from this Remodeled West Maui Studio Just an Elevator Ride Away from the Beach, Pool, and Jacuzzi - Lahaina Shores 331 Welcome to Your Maui Retreat: Enjoy the sights and sounds of the ocean from this cozy, remodeled direct oceanfront studio at Lahaina Shores Beachfront Resort. Perched on the 3rd floor, this West Maui retreat offers spectacular beachfront views from the private furnished lanai, where you can relax with your morning coffee while taking in the sparkling Pacific Ocean and the neighboring islands of Lanai and Molokai in the distance.

Check rates on Whimstay →

No. 356

Breathtaking Mountain Views and Oceanfront Access - Stunning Retreat

Condo

1 bedroom sleeps 4 private pool about $116 a night

NEW LISTING! Experience Lahaina with Breathtaking Panoramic Mountain Views - Lahaina Shores PH 4 Welcome to your Maui Retreat: Escape to the charm of Lahaina Shores Resort with this updated mountain-view 1 bedroom penthouse condo in West Maui. While the condo offers peaceful views of the West Maui Mountains from its private furnished lanai, guests also enjoy direct access to the resort's incredible beachfront setting. Just steps away, you'll find a sparkling oceanfront pool and hot tub overlooking the Pacific, where you can take in breathtaking sunsets and sweeping views of the neighboring islands of Lanai and Molokai.

Check rates on Whimstay →

No. 357

SUMMER SALE! Oceanfront 1BR with Lanai, Pool & Island Views - Lahaina Roads 209

Condo

1 bedroom sleeps 4 private pool about $121 a night

Lahaina Roads 209 Enjoy Spectacular Direct Oceanfront Views, Sunsets, and the Sounds of the Surf from this Freshly Updated West Maui Condo Welcome to Your Maui Retreat: This direct oceanfront 1-bedroom, 1-bathroom condo at Lahaina Roads offers a relaxing and comfortable Maui getaway with unforgettable views. From the moment you step inside, you're greeted by sweeping sights of the Pacific Ocean overlooking the heated oceanfront swimming pool, with the neighboring islands of Lanai and Molokai visible in the distance. The interior blends modern updates with a warm, inviting island feel, creating a comfortable space to unwind after a day of exploring West Maui.

Check rates on Whimstay →

No. 358

Remodeled Oceanfront 1BD with Stunning Sunset Views- Maalaea Banyans 316

Condo

1 bedroom sleeps 4 private pool about $117 a night

Maalaea Banyans 316 Breathtaking Direct Oceanfront Views and Sunsets from this Remodeled 1 Bedroom Maalaea Maui Condo Welcome to Your Maui Retreat: Experience the beauty of Maui's coastline from this remodeled direct oceanfront 1 bedroom, 1 bathroom condo at Maalaea Banyans in Maalaea. Perched on the 3rd floor, the condo features a furnished private lanai with sweeping oceanfront views, where you can enjoy morning coffee, seasonal whale watching, and stunning sunsets over the Pacific. Inside, the bright and airy open living space is designed for comfort and relaxation, with large sliding glass doors that bring the ocean views inside.

Check rates on Whimstay →

No. 359

Royal Kahana 714

Vacation Rental

1 bedroom sleeps 4 private pool about $87 a night

Welcome to Royal Kahana 714. This spacious (777 square feet with a 150-square-foot lanai) 7th floor 1 bedroom, 1 bathroom condo offers ocean and pool views. This unit is tastefully appointed with classic Hawaiiana decor. The bedroom features a king size bed & the living area has a queen sleeper sofa. The condo accommodates 4 guests. Keep cool with central air & ceiling fans throughout the unit. This condo is fully equipped and ready to make amazing Maui memories. Book RK 714 today! WHY YOU’LL LOVE IT. Spacious ocean and pool view condo with classic Hawaiiana décor. Central A/C and ceiling fans throughout for year-round comfort.

Check rates on Whimstay →

No. 360

Royal Kahana 815

Vacation Rental

1 bedroom sleeps 4 private pool about $92 a night

Welcome to Royal Kahana 815. This spacious 8th floor 1 bedroom, 1 bathroom condo offers ocean & surrounding island view. This unit is tastefully appointed with classic tropical decor and has a remodeled kitchen with stainless appliances. The condo accommodates 4 guests. Keep cool with central AC & ceiling fans throughout. This resort offers many amenities and located in a great neighborhood close to food truck parks, shops, farmers market, & more. Book RK 815 today to make amazing Maui memories! WHY YOU’LL LOVE IT. 8th-floor oceanview condo overlooking Moloka‘i and Lāna‘i. Spacious 1BR / 1BA with California King bed and queen sofa sleeper (sleeps 4).

Check rates on Whimstay →