Wailea, Maui

Curated rentals in Wailea

6423 waterfront rentals·30 shores·Every listing on the water·Updated 2026-11-12

Most of Maui's rentals sit on two dry, sunny coasts. West Maui runs from Kapalua through Napili, Honokowai and Kaanapali to Lahaina, with condos set right behind small sandy bays and a view across the channel to Lanai and Molokai. South Maui runs from Maalaea through Kihei to Wailea, where the beaches are wider and a paved path links the resorts. Humpback whales winter in the channel between the islands, and from December to April you can often watch them from a lanai.

StateHI
Peak seasonDecember to March
Best forWaterfront stays
Featured87 rentals
The curated list · 87 rentals

Where we would stay in Wailea, Maui.

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Front Yard is the Beach - Elua 1607
No. 01

Front Yard is the Beach - Elua 1607

Condo
3 bedroom sleeps 6 private pool about $1104 a night

Welcome to your serene oasis at Wailea Elua Village 1607, a luxurious 3-bedroom oceanfront condo that promises an unforgettable stay. This spacious 1,701 sq. ft. retreat comfortably sleeps six guests, featuring a master suite with a king bed, a second bedroom with a queen bed, and a third bedroom with two twin beds. Each bedroom is designed for comfort and privacy, ensuring a restful night's sleep. The condo boasts two full bathrooms, complete with modern fixtures and plush towels. The open-concept living area is perfect for relaxation, with a fully equipped kitchen that includes stainless steel appliances, granite countertops, and all the essentials for a home-cooked meal.

Stunning Wailea Villa with Resort Amenities
No. 02

Stunning Wailea Villa with Resort Amenities

Condo
3 bedroom sleeps 8 private pool about $1116 a night

Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to relax and unwind. A private key-entry elevator transports you directly from your reserved garage parking to your entry lanai, where upscale patio furnishings and lush tropical plants greet you. As you step inside, the entry hall adorned with beautiful artwork leads you to the spacious great room, which boasts stunning ocean views.

3BD Oceanfront - Great for Families
No. 03

3BD Oceanfront - Great for Families

Condo
3 bedroom sleeps 7 private pool about $1201 a night

Welcome to the Makena Surf F112 Beachfront Resort, where luxury meets the ocean's edge. This stunning 3-bedroom, 2-bathroom oceanfront condo is perfect for your dream Hawaiian getaway. The spacious layout features a primary suite with a king bed, a second bedroom with a king bed, and a third bedroom with two day beds, one of which can slide out on the floor and serve as a bonus sleeping option for guests, comfortably sleeping up to seven guests. Step into the open-concept living area, where large windows flood the space with natural light and offer breathtaking views of the Pacific Ocean.

Wailea Beach Villas PH105
No. 04

Wailea Beach Villas PH105

Condo
3 bedroom sleeps 6 private pool about $1238 a night

Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant ocean view penthouse spans 2,500 square feet and features a spacious floor plan that flows seamlessly onto a generous lanai, providing the perfect backdrop for enjoying the island's tropical splendor. Located in a prime position within the Wailea Beach Villas resort, you'll have easy access to a variety of amenities, including sparkling pools and pristine beaches. The beautifully appointed interiors create a comfortable and stylish atmosphere, while tranquil garden views enhance the serene ambiance of your Hawaiian getaway.

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Wailea Beach Villas PH209
No. 05

Wailea Beach Villas PH209

Condo
3 bedroom sleeps 8 private pool about $1247 a night

Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the family pool. This open and airy vacation rental is designed for relaxation and leisure, featuring an expansive tiled great room that seamlessly blends indoor and outdoor living. When the sliding glass doors are fully opened, you can enjoy the gentle breeze while stepping onto your private lanai, where you can catch glimpses of the shimmering Pacific Ocean. The primary suite is thoughtfully situated next to the living area, boasting its own private entrance to the lanai and an en-suite luxury bath for added convenience.

Wailea Beach Villas PH112
No. 06

Wailea Beach Villas PH112

Condo
3 bedroom sleeps 6 private pool about $1283 a night

Awaken to the sweet sounds of palm trees swaying in the tropical breeze from Wailea Beach Villas PH112. Spanning 2,500 square feet, this main level, corner villa fuses a Hawaiian vibe with warm, earthy interior tones. The wraparound lanai offers peekaboo views of the ocean and the surrounding lush grounds. Ideal for large friend groups or couples traveling together, the open floor plan allows for seamless, versatile living. Meticulously designed, the spacious great room encourages gathering as it features an inviting sectional couch, large flat screen TV equipped with Apple TV, and dining area for those nights you want to play games or host a dinner.

Wailea Beach Villas PH309
No. 07

Wailea Beach Villas PH309

Condo
3 bedroom sleeps 8 private pool about $1290 a night

Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private elevator, ensuring privacy and exclusivity. The penthouse features three bedrooms and three bathrooms, with an additional enclosed den that serves as a fourth bedroom. The primary suite is a private retreat with a lavish bathroom complete with a deep-soaker tub, glass shower, and dual sink vanity, and private access to the ocean view lanai.

Spacious Lanai and Lush Tropical Landscapes - Gorgeous Beachfront Retreat
No. 08

Spacious Lanai and Lush Tropical Landscapes - Gorgeous Beachfront Retreat

Condo
3 bedroom sleeps 6 private pool about $1307 a night

This is the one, the best location at Elua. Beachfront 3 BD+3 BA private townhouse with a courtyard and a private beach lanai. New dining room furniture, new glass doors, new bedroom furniture and soft goods highlight this ideal property. If it's available, this is the home-away-from-home that you want for your family. The Wailea Elua Village is a premier property located on the beach in Wailea featuring 152 condos on 24 acres of lush tropical landscapes. Luxury accommodations and breath-taking ocean views in a low-rise, village atmosphere.

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87
curated rentals in Wailea, Maui
Wailea Beach Villas PH508
No. 09

Wailea Beach Villas PH508

Condo
3 bedroom sleeps 8 private pool about $1319 a night

Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layout-perched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design unlike anything else in the resort. This exceptional 3-bedroom + den, 3-bathroom penthouse offers an elevated vacation experience for families or groups seeking space, style, and privacy. Designed with thoughtful luxury, this one-of-a-kind floor plan blends open-concept living with distinct sleeping spaces, allowing up to eight guests to relax and unwind in comfort.

Wailea Beach Villas F201
No. 10

Wailea Beach Villas F201

Villa
3 bedroom sleeps 8 private pool about $1937 a night

Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious 3-bedroom, 3.5-bath villa is perfect for families or couples seeking a serene getaway. Villa F201 is a decorator's dream, harmoniously blending Hawaiiana art, modern furnishings, and Asian accents. Enjoy breathtaking ocean views from both the front lanai and the primary bedroom, complemented by the soothing sound of exterior waterfalls. The inviting oversized sectional sofa and an elegant accent wall adorned with gold-tinted wallpaper create a peaceful ambiance, while engaging artwork enhances the decor.

Wailea Beach Villas D302
No. 11

Wailea Beach Villas D302

Villa
3 bedroom sleeps 8 private pool about $2152 a night

Welcome to Wailea Beach Villas D302! Recently renovated, this residence features a custom gourmet kitchen and dining area, offering a luxurious and spacious retreat in one of Maui's premier locations. Spanning over 2,900 square feet of indoor and outdoor living, it comfortably accommodates families or groups of up to 8 guests. Located on the upper floor of the beachfront villas, D302 provides stunning, unobstructed views of the Pacific Ocean, Wailea Beach, and the surrounding resort area. The expansive private lanai is ideal for enjoying Maui's famous sunsets or al fresco dining while soaking in the panoramic scenery.

Oceanfront with Private Plunge Pool
No. 12

Oceanfront with Private Plunge Pool

Villa
3 bedroom sleeps 8 private pool about $2200 a night

You will feel like a rock star in this oceanfront villa that even has a vinyl record Juke box with complimentary play! Villa B101 sits oceanfront within a secluded garden area surrounding a private plunge pool. A short stroll leads you to the oceanfront infinity pool where adults cool off in peace and tranquility. Cap off your full Maui day in paradise with a warm private outdoor shower located off the primary bathroom. A gourmet kitchen with sub-zero refrigerator, built-in wine refrigerator, and gas stove overlooks the generous dining area and great room. Comfortable seating around the sectional sofa in the living room is perfect for enjoying a good movie on the flat screen TV.

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Mana Kai 811
No. 16

Mana Kai 811

Condo
2 bedroom sleeps 4 about $480 a night

Escape to an oceanfront paradise at Mana Kai 811 - a beautifully appointed 2-bedroom, 2-bath condo on iconic Keawakapu Beach in South Maui. This inviting beachfront retreat boasts king-sized beds in both bedrooms and luxurious modern finishes throughout, perfect for couples, friends, or small families looking to experience Maui's best. With space for up to 4 adults this condo blends comfort and opulent style in every detail, from the open living area to the expansive lanai framing panoramic Pacific views. Step inside this bright and airy unit where natural light fills the living space, and the ocean's rhythm becomes your soundtrack.

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Oceanfront Paradise with Spacious Lanai - Stunning Coastal Retreat
No. 18

Oceanfront Paradise with Spacious Lanai - Stunning Coastal Retreat

Condo
2 bedroom sleeps 5 about $481 a night

Welcome to Mana Kai 304, your private slice of oceanfront paradise on Maui. This fully renovated two-bedroom, two-bathroom condo was completely remodeled in 2025 and offers a fresh, modern retreat with high-end finishes and thoughtful details throughout. From brand-new floors and cabinetry to updated bathrooms and fixtures, every inch of this luxury vacation rental has been designed for comfort and relaxation. Whether you're here for a romantic getaway or a family escape, this home is the perfect base for your Maui adventure. Inside the condo, natural light floods the open-concept living space, where floor-to-ceiling windows frame breathtaking views of the Pacific Ocean.

Beachfront Condo - Hear the Waves Crash
No. 20

Beachfront Condo - Hear the Waves Crash

Condo
2 bedroom sleeps 6 private pool about $503 a night

Welcome to the Makena Surf C207 Beachfront Resort, your idyllic retreat nestled in the heart of Wailea. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a perfect blend of luxury and comfort, ideal for families or groups of friends. Step inside to discover a spacious, open-concept living area with a cozy sofa bed, perfect for unwinding after a day of adventure. The gourmet kitchen is fully equipped with modern appliances, including a refrigerator, oven, microwave, and dishwasher, making meal preparation a breeze. The master bedroom features a plush king bed, while the second bedroom comfortably accommodates two guests with a set of twin beds.

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Oceanfront Makena Surf G202 - Professionally
No. 21

Oceanfront Makena Surf G202 - Professionally

Condo
2 bedroom sleeps 6 private pool about $557 a night

Welcome to the Makena Surf G202 Beachfront Resort, your perfect oasis in Wailea, Hawaii. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a luxurious escape for up to six guests. Step inside to find a spacious, open-concept living area that seamlessly blends modern elegance with coastal charm. The living room features a comfortable sofa bed, perfect for unwinding after a day at the beach. The master bedroom boasts a plush king bed, ensuring a restful night's sleep, while the second bedroom offers two twin beds, ideal for families or friends. Both bathrooms are fully equipped with all necessary amenities, including premium toiletries and fluffy towels.

Spacious Lanai and Gourmet Kitchen - Elegant Maui Retreat
No. 22

Spacious Lanai and Gourmet Kitchen - Elegant Maui Retreat

Condo
2 bedroom sleeps 6 private pool about $563 a night

Welcome to Wailea Elua 808, your ideal Maui retreat. This spacious 2-bedroom, 2-bath condo offers the perfect setting for a relaxing getaway or a family vacation. With a thoughtfully designed floor plan, stylish furnishings, and ample natural light, you'll feel at home the moment you arrive. The well-appointed kitchen is fully equipped for all your culinary needs, whether you're preparing a quick breakfast or a sunset dinner. The living area opens up to a private lanai, creating a seamless indoor-outdoor experience ideal for enjoying island breezes and al fresco dining.

Makena Surf C105 Beachfront Resort
No. 23

Makena Surf C105 Beachfront Resort

Condo
2 bedroom sleeps 6 private pool about $612 a night

Welcome to the Makena Surf C105 Beachfront Resort, a stunning 2-bedroom oceanfront condo nestled in the heart of Wailea, Hawaii. This luxurious retreat offers a perfect blend of comfort and elegance, ideal for families or groups of friends seeking a memorable beach getaway. Step inside to discover a thoughtfully designed layout that maximizes space and natural light. The open-concept living area features a cozy, fully equipped kitchen with modern appliances, perfect for preparing meals. Adjacent to the kitchen, the dining area comfortably seats six, making it ideal for sharing meals and stories around the table.

Whale Watch From Your Lanai
No. 24

Whale Watch From Your Lanai

Condo
2 bedroom sleeps 4 private pool about $628 a night

Welcome to the Makena Surf E302 Beachfront Resort, your perfect oasis in Wailea, HI. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a luxurious retreat for up to four guests. Step into the open-concept living space, where modern design meets comfort. The living area features a cozy sofa, a flat-screen TV with cable, and a dining area that seats six, perfect for enjoying meals with family and friends. The kitchen is fully equipped with stainless steel appliances, granite countertops, and all the essentials you need to prepare delicious meals. Both bedrooms are spacious and inviting, with the master bedroom featuring a king bed and the second bedroom offering a queen bed.

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Stunning Living Room and Lanai Furniture - Charming Escape
No. 25

Stunning Living Room and Lanai Furniture - Charming Escape

Condo
2 bedroom sleeps 6 private pool about $668 a night

Please note there is construction work to the right of the property by the Andaz from August 18th to 25th that will be pretty noisy Wailea Elua Village #2301 is a premier vacation condominium located in Elua Village which is directly on the sugar sand of Ulua beach in Wailea. This impressive vacation condominium is constantly in high demand with new living room furniture and lanai furniture - Absolutely Lovely, plus a king-sized bed in the primary bedroom and two single beds in the guest bedroom which can be converted into a 'king' sized bed upon request, and a Queen-sized sofa bed.

Makena Surf F207 Beachfront Resort
No. 26

Makena Surf F207 Beachfront Resort

Condo
2 bedroom sleeps 6 private pool about $689 a night

Welcome to the Makena Surf F207, where luxury meets the ocean's edge. This beautifully renovated 2-bedroom, 2-bathroom oceanfront condo is perfect for your dream Maui getaway. The spacious 1,313 square foot open features floor-to-ceiling windows that bring the ocean views and natural lighting into the living room, kitchen, and dining area. Spend gentle mornings on your lanai sipping coffee and gazing out at the ocean reefs that front the condo. Search for turtles patrolling the reefs, dolphins playing offshore, or even humpback whales breaching during the winter months.

Makena Surf G105 Beachfront Resort
No. 27

Makena Surf G105 Beachfront Resort

Condo
2 bedroom sleeps 6 private pool about $719 a night

Welcome to the enchanting Makena Surf G105 Beachfront Resort, your perfect haven nestled in the heart of Wailea. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a luxurious escape for up to six guests. Step into the spacious living room, where you'll find a cozy twin-sized sleeper sofa, perfect for unwinding after a day of adventure. The gourmet kitchen is fully equipped with modern appliances, including a refrigerator, oven, microwave, and dishwasher, making it easy to prepare delicious meals. The master bedroom features a plush king bed, offering a serene retreat with direct access to the balcony, where you can soak in the breathtaking ocean views.

Recently Renovated - Oceanfront in Wailea
No. 28

Recently Renovated - Oceanfront in Wailea

Condo
2 bedroom sleeps 4 private pool about $800 a night

Welcome to the serene and luxurious Wailea Elua Village 1604, your perfect ocean front retreat in Wailea. This stunning 2-bedroom, 2-bathroom condo offers a blend of modern elegance and comfort, ideal for a family or group of friends. The open-plan living area seamlessly connects to a private balcony, where you can soak in the breathtaking ocean views and gentle sea breezes. Step inside to discover a thoughtfully designed interior. The master bedroom features a plush king bed and an en-suite bathroom with premium amenities. The second bedroom comfortably accommodates two guests with twin beds, ensuring a restful night's sleep.

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Beachfront Condo - Location, Location, Location
No. 29

Beachfront Condo - Location, Location, Location

Condo
2 bedroom sleeps 4 private pool about $851 a night

Welcome to the serene and luxurious Wailea Elua Village 1001, a stunning 2-bedroom oceanfront condo nestled in the heart of Wailea. This meticulously designed property offers a perfect blend of comfort and elegance, ideal for your dream vacation. Step inside to discover a spacious, open-plan living area that seamlessly flows into a private balcony, offering breathtaking views of the ocean. The living room is adorned with plush furnishings and modern decor, creating a cozy yet sophisticated atmosphere. The fully equipped kitchen features stainless steel appliances, granite countertops, and all the essentials you need for a memorable stay.

Wailea Elua Village 1603
No. 30

Wailea Elua Village 1603

Condo
2 bedroom sleeps 6 private pool about $872 a night

Welcome to the serene and luxurious Wailea Elua Village 1603, a stunning 2-bedroom ocean front condo nestled in the heart of Maui’s resort town of Wailea. “Oceanfront” literally means that the only thing separating your ground floor lanai from the ocean is landscaped and manicured lawns! The home is highlighted by its inviting and oversized lanai. Plan gentle mornings lounging on the comfortable chaise loungers with coffee and banana bread in hand as you access the ocean conditions. Carve out time for sunset appetizers and drinks as the gentle trade winds cool you off. Lastly, recline on the loungers at night and gaze up at Maui’s night sky filled with thousands of twinkling stars.

Wailea Elua Village 1303
No. 31

Wailea Elua Village 1303

Condo
2 bedroom sleeps 4 private pool about $894 a night

Welcome to the serene and luxurious Wailea Elua Village 1303, your perfect short-term rental in the heart of Wailea. This stunning 2-bedroom, 2-bathroom ocean front condo offers a blend of modern elegance and comfort, ideal for your Hawaiian getaway. Step inside to discover a spacious, open-concept living area with sleek, contemporary design. The living room features a cozy seating area with a flat-screen TV and high-speed Wi-Fi, perfect for streaming your favorite shows. The fully equipped kitchen includes stainless steel appliances, granite countertops, and all the essentials for preparing delicious meals.

Wailea Beach Villas PH104
No. 32

Wailea Beach Villas PH104

Condo
2 bedroom sleeps 6 private pool about $1109 a night

Marvel at the sophisticated style and decor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted matting behind the impressive 85'' living room TV and a charming wooden picnic-table style dining table. This vacation rental promises to enchant you with its unique aesthetic. The penthouse features a den off the living room, which can be partitioned with sliding doors to provide a private sleeping arrangement for additional guests.

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Wailea Beach Villas PH106
No. 33

Wailea Beach Villas PH106

Condo
2 bedroom sleeps 6 private pool about $1109 a night

Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui's most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional choice for families or small groups seeking a five-star getaway in Wailea. Inside, you'll find two beautifully designed bedrooms, along with a versatile den that doubles as a third sleeping area - comfortably accommodating up to six guests. The open-concept living and dining areas are tastefully furnished with updated decor, creating a warm, inviting space to relax after a day in the sun.

Wailea Beach Villas PH111
No. 34

Wailea Beach Villas PH111

Condo
2 bedroom sleeps 6 private pool about $1109 a night

Curated with our guests in mind, Wailea Beach Villas PH111's outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located nearby for additional endless entertainment and relaxation. Step inside to discover serene Earthy hues, wood accents, and contemporary finishes. The sun-filled, open floor plan offers seamless continuity between the versatile living spaces and opportunities for shared enjoyment and experiences.

Wailea Beach Villas PH307
No. 35

Wailea Beach Villas PH307

Condo
2 bedroom sleeps 6 private pool about $1109 a night

In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view vacation residence will cultivate long lasting memories and leave you feeling rejuvenated upon departure. Centrally located on property at the Wailea Beach Villas, enjoy blissful sunset views with prime access to your favorite on-property amenities like the family game room, two pools, and fitness center. The sun-splashed, open floorplan ushers in an abundance of natural light into the home.

Wailea Beach Villas PH211
No. 36

Wailea Beach Villas PH211

Condo
2 bedroom sleeps 6 private pool about $1110 a night

Indulge in entertainment abound when vacationing in Wailea Beach Villas Penthouse 211. After you've spent an action-packed day at the beach or hiking one of Maui’s scenic trails, return to your vacation residence and discover some more relaxing entertainment options that will bring a smile to your face. Whether you choose to put in your favorite movie on the large 60” flat screen TV or test your skills at the custom-built arcade machine equipped with fan-favorite video games, there will be no dull moment on your trip to Hawaii! Or take it easy on the spacious lanai and appreciate the gorgeous ocean views.

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Wailea Beach Villas PH404
No. 37

Wailea Beach Villas PH404

Condo
2 bedroom sleeps 6 private pool about $1119 a night

Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho'olawe and Molokini, creating the perfect backdrop for your Maui vacation. The private lanai with Viking grill is ideal for relaxing with morning coffee or savoring vibrant island sunsets in the evenings. Inside, Penthouse 404 is beautifully furnished with island-inspired decor and top-quality finishes. The spacious living and dining areas offer a refined yet welcoming ambiance.

Wailea Beach Villas PH504
No. 38

Wailea Beach Villas PH504

Condo
2 bedroom sleeps 6 private pool about $1128 a night

Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kaho‘olawe, Molokini crater, and Lanai. This generous two-bedroom, two-bathroom condo provides over 1900 sq. ft. of living space, outdoor lanai, entertaining space, plus a den. Located on the fifth floor, guests can take advantage of the elevated views! Lounge on the scenic private lanai where you can take in picture perfect sunsets and whale watching views. Humpback Whales provide hours of acrobatic entertainment, breaching and slapping the water for our sheer delight from mid-November thru April each year. With its amazing views, Penthouse 504 provides a prime vantage point for their show.

Oceanfront Views and Spacious Lanai - Stunning Beachfront Oasis
No. 39

Oceanfront Views and Spacious Lanai - Stunning Beachfront Oasis

Condo
2 bedroom sleeps 4 private pool about $1150 a night

Ulua Beach Front Row 2-Bedroom Oceanfront Unit. Unobstructed Ocean Views! Welcome to Wailea Ulua #1002! This recently renovated luxury beachfront 2 bedroom/2 bath residence is located in the heart of Wailea on Maui Sunny South Shore. Within steps of the unit you are on one of Maui’s best beaches. Ulua Beach is ideal for family fun, snorkeling, swimming, diving, paddle boarding, or just relaxing. This unit is fully equipped and ready for all your vacation needs. You will enjoy the stunning ocean views from the Lanai and throughout the unit. During the winter months you can whale watch from the lanai and living room.

Wailea Beach Villas PH410
No. 40

Wailea Beach Villas PH410

Condo
2 bedroom sleeps 6 private pool about $1176 a night

Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kaho'olawe, Molokini and Lana'i. From your private elevator landing, the suite opens with a wide hallway leading past both bedrooms toward the great room where a generous living room features a large, flat screen TV and plush furnishings. Furnished in a classic island theme and accented with bamboo cabinetry, this two-bedroom penthouse blends contemporary style with traditional artwork and décor for a classy and comfortable retreat.

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Wailea Beach Villas PH406
No. 41

Wailea Beach Villas PH406

Condo
2 bedroom sleeps 6 private pool about $1179 a night

Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and an amazing ocean view. The luxurious and expansive sightline is visible from the front entry and boasts 180-degree views which include the nearby islands of Molokini Crater, Kahoolawe and Lanai. The well-furnished balcony includes a table and chairs for four, recliner lounge chair, as well as a Viking rotisserie grill.

Breathtaking Views and Direct Beach Access - Stunning Oceanfront Escape
No. 42

Breathtaking Views and Direct Beach Access - Stunning Oceanfront Escape

Condo
1 bedroom sleeps 4 about $225 a night

Experience the ultimate ocean immersion at Punahoa Beach 201 and live your Maui adventure right on the beach with immediate access to the protective, warm-water swimming and vibrant snorkeling reef for which Kamaole I Beach is world renowned. Spectacular forever ocean views await from your lanai and caressing tropical breezes blow right off the ocean. Kamaole I Beach is one of Maui's best stretches of sand and will be your gateway to the meandering beach path that meanders for miles to the South, past the Wailea resorts and Kamaole II and III Beaches.

Spacious Condo on Favorite Local Beach
No. 43

Spacious Condo on Favorite Local Beach

Condo
1 bedroom sleeps 4 shared pool about $247 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 54B A recently remodeled 1,180 sq.ft. 2nd-floor condo with 2 full bathrooms, offering peaceful elevated living with a private balcony overlooking ocean over resort gardens. Stroll through 34 acres of tropical gounds to Keawakapu Beach, swim in 4 resort pools, play pickleball and walk to Ekahi's beachfront pavilion. Perfect for couples or families up to 4, within short walk to Wailea's top shopping and dining. WHY OUR GUESTS LOVE IT. Newly Remodeled Kitchen: Just completed a full remodel featuring modern finishes and quality appliances.

Tranquil Lanais and Lush Gardens - Serene Tropical Retreat
No. 44

Tranquil Lanais and Lush Gardens - Serene Tropical Retreat

Condo
1 bedroom sleeps 4 private pool about $275 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. *. * At Wailea Ekahi, it's all about location - some of the units at the property are up the hill, and a real hassle to get to the beach. The doorstep of Wailea 20J is a leisurely 5-minute stroll to one of the best beaches in the Hawaiian islands - Keawakapu Beach (Google it) - with its warm, protected swimming cove, spectacular snorkeling, and more than a mile of beautiful Hawaiian beach to explore.

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Platinum Rated and Professionally Managed
No. 45

Platinum Rated and Professionally Managed

Condo
1 bedroom sleeps 4 private pool about $276 a night

Welcome to the serene Wailea Ekahi Village 26D, a luxurious 1-bedroom, 2-bathroom garden view condo nestled in the heart of Wailea. This meticulously designed 945 sq. ft. retreat comfortably sleeps up to four guests, offering a perfect blend of elegance and comfort for your Hawaiian getaway. Step inside to discover a spacious living room with a cozy Murphy bed, ideal for unwinding after a day of exploration. The master bedroom features a plush king-sized bed, ensuring a restful night's sleep. Both bathrooms are fully equipped with modern amenities, providing a spa-like experience.

Wailea Ekahi Village 30D
No. 46

Wailea Ekahi Village 30D

Condo
1 bedroom sleeps 4 shared pool about $335 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 30D This spacious 945 sq.ft. 1-bedroom condo with 2 full bathrooms offers elevated ocean and sunset views over tropical gardens and pickleball courts from your 2nd-floor lanai. Take a scenic 3-minute walk through 34 acres of botanical gardens to Keawakapu Beach, swim in 4 resort pools, and pack easy to the oceanfront pavilion with provided beach gear. You are also minutes from Wailea's best dining and shopping. WHY OUR GUESTS LOVE IT. Sunset Ocean Views: The private covered lanai offers beautiful, elevated views of the Pacific Ocean and stunning evening sunsets.

Stunning Ocean Vistas and Resort-Style Amenities - Luxurious Coastal Escape
No. 47

Stunning Ocean Vistas and Resort-Style Amenities - Luxurious Coastal Escape

Condo
1 bedroom sleeps 4 private pool about $338 a night

Welcome to Wailea Ekahi 39E, a beautifully appointed one-bedroom, two-bath condo offering breathtaking ocean views and the perfect blend of comfort, style, and convenience. Whether you're planning a romantic retreat, a peaceful solo vacation, or a productive remote work escape, this coastal haven delivers an unforgettable Maui experience. The open-concept living space is infused with natural light from expansive windows that frame panoramic views of the Pacific. A plush queen-size sofa sleeper invites relaxation, while a 65” smart TV offers entertainment for cozy evenings in.

Beachfront Condo with Postcard Views
No. 48

Beachfront Condo with Postcard Views

Condo
1 bedroom sleeps 4 shared pool about $508 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Elua Village 1301 Elua Village sits adjacent to Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk, the most beach-accessible address in the area. Unit 1301 sits near the front of the complex, 150 yards from the sand, with a private oceanfront patio. Beach chairs, two resort pools, a shared hot tub, and 24 acres of tropical grounds. The Andaz is a scenic stroll up the coast. South Maui's best snorkeling is across the lawn. WHY OUR GUESTS LOVE IT. Box Seats to the Ocean: Near the front of the complex, the private patio looks directly out to the Pacific, unobstructed ocean and sunset views, 150 yards from Ulua Beach.

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Prime Location. Snorkeling. Wailea Beach Path
No. 49

Prime Location. Snorkeling. Wailea Beach Path

Condo
1 bedroom sleeps 2 private pool about $524 a night

Welcome to your serene oasis at Wailea Elua Village 1203, a stunning 1-bedroom, 2-bathroom oceanfront condo that promises an unforgettable stay. As you step inside, you'll be greeted by a modern, open-concept living space that seamlessly blends comfort with elegance. The living room features plush seating, a smart TV with cable, and a cozy fireplace, perfect for unwinding after a day of exploration. The fully-equipped kitchen boasts stainless steel appliances, granite countertops, and all the essentials you need to prepare delicious meals. The dining area offers a table for two, allowing you to enjoy your meals with stunning ocean views.

Wailea Ekahi Village 44B
No. 50

Wailea Ekahi Village 44B

Condo
sleeps 2 shared pool about $211 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 44B A recently remodeled 600 sq.ft. ground-floor studio, offering step-free access and a lovely garden lanai with private gas BBQ. Located just steps from 1 of 4 resort pools, pickleball courts and a pleasant walk down a grassy hill to the beachfront pavilion and Keawakapu Beach. Perfect for couples, sleeping 2 with a plush king bed and walkable to the best Wailea shopping and dining. WHY OUR GUESTS LOVE IT. Recently Remodeled: The beautiful interior features a newly upgraded kitchen and stylish modern finishes throughout. Steps to the Pool: Located just steps away from a refreshing resort pool for effortless swims.

Luxury Pool and Hot Tub Access - Spacious Family Retreat
No. 51

Luxury Pool and Hot Tub Access - Spacious Family Retreat

Condo
3 bedroom sleeps 8 private pool about $282 a night

3Bedroom, 2Bathroom, 2nd Floor Wailea Condo with Central AC, Pool, Hot Tub. Perfect for a Family Getaway. Close to Beaches, Restaurants, Shopping, Tennis, Golf - Grand Champions 124. Professionally managed. Welcome to your Maui Retreat: Grand Champions 124 is the vacation destination that you and your family have been dreaming of! This spacious 3 bedroom, 2 bathroom home sleeps 8 people and is located in beautiful Wailea on the South side of Maui. Come and relax out on your private lanai, take in the view and feel the tropical breeze. This home is fully stocked with everything you ll need during your Hawaiian vacation. A stay at Grand Champions is one you won t soon forget.

Oceanfront Pool and Snorkeling - Luxurious Tropical Getaway
No. 52

Oceanfront Pool and Snorkeling - Luxurious Tropical Getaway

Condo
2 bedroom sleeps 4 private pool about $510 a night

Mana Kai Maui is Kihei's most exclusive vacation rental resort, with its location on the sand on Keawakapu Beach - and this unit features a prime location in the building, with sweeping views down the south Maui shoreline, to the Wailea resorts. Fabulous snorkeling directly in front of the building, warm-water swimming, ideal for stand-up paddle boarding and kayaking: this location has it all for the ultimate Maui beach experience. Mana Kai 410 is located conveniently on the 4th floor near the center of the building. Sleep the sound of the waves and experience one of the island's best ocean views from your living room and lanai.

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Oceanfront Access and Stunning Views - Luxurious Island Retreat
No. 53

Oceanfront Access and Stunning Views - Luxurious Island Retreat

Condo
2 bedroom sleeps 6 private pool about $721 a night

*. *. * Renovation projects are scheduled from April 6 through November 20, 2026 in units G-102, G-105, and G-303. Guests may experience intermittent noise and minor disruptions. *. *. Makena Surf G-201 is on one of the most luxurious and prestigious properties on the island of Maui. With oceanfront access and spectacular views, it offers a secluded and tranquil setting for your next island getaway. Unit G201 is located on the second floor of the G building and enjoys a panoramic view of a small, secluded cove and the beautiful Pacific Ocean. The soft sandy beach and world class snorkeling is only steps away. You might even get to watch a sunset wedding right on the beach!

Charming Ground-Floor Oasis with Pools and Daily Activities - Gorgeous Retreat
No. 56

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.

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Wailea Ekahi Village 18C
No. 57

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.

Tropical Oasis with Expansive Lanai - Serene Island Retreat
No. 58

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.

Lush Landscaped Grounds and Relaxing Pools - Stunning Beachfront Haven
No. 59

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.

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Oceanfront Lanai and Scenic Views - Stunning Hawaiian Retreat
No. 62

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!

Watch Sunsets Over the Ocean
No. 63

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.

Ocean View and Spacious Patio - Stunning Beachfront Escape
No. 64

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.

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Tropical Serenity and Luxury Amenities - Stunning Coastal Retreat
No. 65

Tropical Serenity and Luxury Amenities - Stunning Coastal Retreat

Condo
3 bedroom sleeps 6 private pool about $807 a night

Welcome to Wailea Elua 805, a beautifully remodeled 3-bedroom, 2-bathroom vacation rental located in the exclusive, gated beachfront community of Wailea Elua Village on Maui's stunning south shore. Just a two-minute stroll to Ulua Beach, one of Wailea's top snorkeling spots, this spacious single-level retreat offers the perfect blend of modern luxury, tropical serenity, and island convenience. With nearly 1,700 square feet of interior space and an additional private courtyard and lanai, this Wailea vacation rental was designed for seamless indoor-outdoor living.

Wailea Condo Great for Families
No. 66

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.

Wailea Ekahi 17B - Professionally Managed
No. 67

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.

Beachfront & Modern. Makena Surf A102
No. 68

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.

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Luxury Oceanfront Mana Kai Resort Condo
No. 69

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.

Makena Surf A204 Beachfront Resort
No. 70

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.

Recently Renovated at Wailea Beach Villas
No. 71

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.

Oceanfront Polo Beach 407 - Professionally Managed
No. 72

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.

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Wailea Beach Villas PH306
No. 73

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.

Wailea Ekahi Village 7A
No. 74

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.

Top-Floor Elegance and Premium Amenities - Stunning Retreat
No. 75

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!

Wailea Beach Villas PH403
No. 76

Wailea Beach Villas PH403

Condo
3 bedroom sleeps 8 private pool about $1267 a night

Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square feet, this penthouse features three bedrooms and three full bathrooms, making it an ideal holiday retreat. Guests can enjoy breathtaking Maui sunsets from the expansive 375-square-foot covered lanai, perfect for relaxation. Upon entering, you are greeted by a formal entry hall adorned with tasteful artwork, setting a welcoming tone. The spacious great room seamlessly connects the upscale living area with a dining space that accommodates six, along with three additional bar stools at the kitchen counter.

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Wailea Beach Villas E202
No. 77

Wailea Beach Villas E202

Villa
3 bedroom sleeps 8 private pool about $1662 a night

Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color throughout, accentuating the natural light, swaying palms and fresh air of Maui. Two primary bedroom suites and a third bedroom with a private lanai and bath on the far side of the villa make traveling with other couples or extended family easy and enjoyable.

Wailea Beach Villas G302
No. 78

Wailea Beach Villas G302

Villa
3 bedroom sleeps 8 private pool about $2243 a night

Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking grill-perfect for sunset barbecues in a tranquil island atmosphere. Designed with comfort in mind, Villa G302 boasts two primary bedroom suites and a third bedroom, each with its own private lanai and bathroom, making it ideal for groups or couples traveling together. If you have a musician in your party, enjoy the soothing sounds from the baby grand piano while lounging on the sectional sofa in the great room.

Recently Renovated - Oceanfront in Makena
No. 79

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.

Makena Surf G203. Serene Oceanfront Hideaway
No. 80

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.

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Makena Surf B305 Beachfront Resort
No. 81

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.

Hear the Waves Crash - Oceanfront
No. 82

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.

Wailea Beach Villas PH210
No. 83

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.

Wailea Beach Villas PH502 - Professionally Managed
No. 84

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.

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Wailea Ekahi Vilage 20D
No. 85

Wailea Ekahi Vilage 20D

Condo
1 bedroom sleeps 4 private pool about $244 a night

CORALTREE RESIDENCE COLLECTION presents. Wailea Ekahi Village 20D This spacious 1-bedroom condo is a short walk from Keawakapu Beach, one of South Maui's calmest, most uncrowded shores, where sea turtles glide offshore year-round. At 945 square feet, the roomy condo sleeps up to 4 and is ideal for couples and small families. The Wailea Ekahi Village residential resort has four pools, pickleball courts, and an oceanfront BBQ pavilion. The start of the coastal Wailea Beach Path is also a short stroll along the beach away. WHY OUR GUESTS LOVE IT.

Wailea Ekahi 52D
No. 86

Wailea Ekahi 52D

Condo
1 bedroom sleeps 4 private pool about $269 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 52D, a beautifully renovated one-bedroom retreat in the heart of Wailea offering the perfect blend of island elegance, comfort, and privacy. Set within the lush tropical grounds of the highly sought-after Wailea Ekahi Village, this spacious second-floor condo has been thoughtfully upgraded to create a relaxing and refined Maui escape.

Wailea Ekahi 42C
No. 87

Wailea Ekahi 42C

Condo
1 bedroom sleeps 4 private pool about $320 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. *. * Wailea Ekahi 42C is a private 1-bedroom, 2-bath vacation rental tucked into one of the quieter garden settings within Wailea Ekahi Village. This thoughtfully designed Maui condo offers a relaxed indoor-outdoor layout, peekaboo ocean views from the lanai, and a shaded tropical backdrop that gives the unit a calm, residential feel. Its location near the quiet pool adds to the sense of privacy, making it a strong choice for guests who want comfort, convenience, and a more peaceful Wailea stay.

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Curated luxury alternative

Prefer a boutique hotel or villa?

If a hand-picked, design-led hotel sounds better than a vacation rental, Skylark Travel Group covers the same destinations with curated boutique stays, Mr & Mrs Smith, exclusive deals, real human concierge.

Sponsored.

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