Big Island

No. 01

Little Kona Getaway with AC & heated oceanfront pool 1 BD 1 BA with sleeper sofa

Condo

1 bedroom sleeps 4 private pool about $93 a night

1-bedroom condo at Aliʻi Villas includes a sleeper sofa, an oceanfront heated pool, and features new split AC systems. Conveniently located in the heart of Kailua-Kona, this property is close to restaurants, shops, local attractions, and entertainment. Private lanai, full kitchen, in-unit washer/dryer, free WiFi, and free parking for one vehicle. On-site BBQ area with gas grills and outdoor dining. Close to snorkeling, surfing, golf and ocean activities. Located on the 2nd floor (no elevator access). No pets. No smoking in the unit, on the lanai, or in the complex.

Check rates on Whimstay →

No. 02

Oceanfront Pools and Sandy Beach - Charming Tropical Retreat

Condo

1 bedroom sleeps 3 private pool about $98 a night

Ground Floor Kona Condo w/ A/C. Walk to Oceanfront Pool & Sunsets Relax into island living at Casa de Emdeko 121, a charming ground-floor condo along historic Aliʻi Drive, just 1.5 miles from downtown Kailua-Kona. This updated one-bedroom retreat offers air-conditioned comfort, easy access, and a peaceful tropical setting within one of Kona's most loved oceanfront communities. Whether you're sipping coffee on your lanai, lounging by the pool, or watching sunset along the oceanfront, this is the perfect home base for your Big Island escape. Why Guests Love This Condo. Ground-floor access, no stairs, easy entry. Air conditioning for added comfort. King bed ideal for couples.

Check rates on Whimstay →

No. 03

Saltwater Pool and Oceanfront Gathering Space - Beautiful Kona Retreat

Condo

1 bedroom sleeps 4 private pool about $101 a night

vrKCV - Casa de Emdeko 114, Professionally Managed Ground-Floor Kona Condo. Central A/C. Steps to Oceanfront Pool Relax into island living at Casa de Emdeko 114, a beautifully updated ground-floor condo on Aliʻi Drive. Enjoy central air conditioning, easy access to two pools, and one of Kona's most loved oceanfront gathering spaces, all just minutes from downtown.

Check rates on Whimstay →

No. 04

Ocean Access and Solar Heated Pool - Charming Island Getaway

Condo

1 bedroom sleeps 2 private pool about $102 a night

Monthly rates available until October 1st This newly remodeled ground floor one bedroom condo is perfect for your island getaway. Comfortably furnished and well equipped, just bring your suitcase Short walk to your parking space and pool area.Perfect for visitors with mobility issues Note: There is a standalone air conditioner in the bedroom. Lush gardens, solar heated pool, BBQ and picnic area, oceanfront seating, ocean access for the expert swimmer and of course those famous Kona Sunsets. This is a non-smoking complex. Free WiFi and digital cable. All reservations are required to digitally sign a rental agreement between the person booking and and property manager to be confirmed.

Check rates on Whimstay →

No. 05

Ocean Access and Solar Heated Pool - Delightful Island Retreat

Condo

1 bedroom sleeps 4 private pool about $107 a night

This sweet one bedroom condo is perfect for your island getaway. Comfortably furnished and well equipped, just bring your suitcase. Newly installed Spilt A/C unit in main living area and bedroom. Short walk to your parking space and pool area. Ocean shoreline and pool view from the lanai. Queen sofa bed in Living Room. Lush gardens, solar heated pool, BBQ and picnic area, oceanfront seating, ocean access for the expert swimmer and of course those famous Kona Sunsets. This is a non-smoking complex. Free WiFi and digital cable. All reservations are required to digitally sign a rental agreement between the person booking and and property manager to be confirmed.

Check rates on Whimstay →

No. 06

Beach Front Resort-Balcony, Zona Hotelera, Cancún

Beachfront

about $111 a night

Wonderful beachfront resort in Zona Hotelera, Cancún with balcony views.

Check rates on Vrbo →

No. 07

Oceanfront Saltwater Pool and Tropical Gardens - Inviting Coastal Retreat

Condo

1 bedroom sleeps 4 private pool about $111 a night

vrKCV - Casa de Emdeko 110, Professionally Managed Ground Floor Kona Condo. Steps to Oceanfront Pool & Sunsets Welcome to Casa de Emdeko #110, a beautifully updated ground-floor condo in one of Kailua-Kona's most iconic oceanfront communities. Offering central air conditioning, a private lanai, and easy access to the oceanfront saltwater pool, this inviting retreat is ideal for couples or small families. Located just 1.5 miles from downtown Kona, you'll enjoy the perfect balance of relaxation and convenience along historic Aliʻi Drive.

Check rates on Whimstay →

No. 08

Courtyard Kona Condo w/ AC + Oceanfront Pools. Casa 202

Condo

1 bedroom sleeps 2 private pool about $116 a night

Courtyard Kona Condo w/ AC + Oceanfront Pools. Casa 202 Peaceful Kona escape just minutes from town Courtyard views + central A/C for total comfort Oceanfront pools, sandy beach area & sunset BBQs Welcome to Casa de Emdeko 202, a beautifully updated 1-bedroom condo offering a peaceful courtyard setting just 1.5 miles from downtown Kailua-Kona. Ideal for couples, this inviting retreat features central air conditioning, a renovated kitchen and bath, and the convenience of an in-unit washer and dryer. Enjoy the best of both worlds, quiet relaxation at home and easy access to beaches, dining, and activities along Alii Drive.

Check rates on Whimstay →

No. 09

Cozy Outdoor Dining and Tropical Essentials - Charming Hawaiian Retreat

House

3 bedroom sleeps 7 about $119 a night

Welcome to Larae’s Place! This cozy 3BR/1BA home comfortably accommodates up to 7 guests. Located minutes from local beaches, shopping, and the airport, it's perfect for exploring Hilo. Relax in the outdoor dining area and enjoy all the essentials needed for a tropical retreat. THE SPACE. 3 well-appointed bedrooms with Portable A/C in each ⎯ Master: King bed (sleeps 2) ⎯ Bedroom #2: Queen bed (sleeps 2) ⎯ Bedroom #3: 2 twin beds (sleeps 2) ⎯ Living Room: Full daybed (sleeps 1). 1 Bathroom w/ quality bath essentials. Fresh linens + towels provided. Fully equipped kitchen. In-unit washer + dryer. Cable TV and high-speed internet.

Check rates on Whimstay →

No. 10

Charming Outdoor Dining and Tropical Essentials - Cozy Island Retreat

House

3 bedroom sleeps 7 about $119 a night

Welcome to Larae’s Place! This cozy 3BR/1BA home comfortably accommodates up to 7 guests. Located minutes from local beaches, shopping, and the airport, it's perfect for exploring Hilo. Relax in the outdoor dining area and enjoy all the essentials needed for a tropical retreat. THE SPACE. 3 well-appointed bedrooms with Portable A/C in each ⎯ Master: King bed (sleeps 2) ⎯ Bedroom #2: Queen bed (sleeps 2) ⎯ Bedroom #3: 2 twin beds (sleeps 2) ⎯ Living Room: Full daybed (sleeps 1). 1 Bathroom w/ quality bath essentials. Fresh linens + towels provided. Fully equipped kitchen. In-unit washer + dryer. Cable TV and high-speed internet.

Check rates on Whimstay →

No. 11

Ocean Access and Lush Courtyard - Charming Island Retreat

Condo

1 bedroom sleeps 4 private pool about $119 a night

Affordable Ground-Floor Kona Condo with Ocean Access, Pools and Lanai - Casa De Emdeko by the property manager Now Available for Sale - Own Your Slice of Paradise Experience unbeatable value and island comfort at Casa De Emdeko by the property manager, a beautifully remodeled 1-bedroom, 1-bathroom ground-floor condo in Kailua-Kona, Hawaii. This competitively priced vacation rental is perfect for couples, families, solo travelers, or snowbirds looking for the perfect balance of affordability, convenience, and resort-style living. Plus, this sought-after property is currently for sale, making it a rare opportunity to own your own piece of paradise.

Check rates on Whimstay →

No. 12

Private Lanai and Scenic Pool Access - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 shared pool about $122 a night

Ali'i Villas on Hawaiʻi island is home to some of the most pristine waters in the world. With a pool facing epic sunsets, nestled on top of natural volcanic rock, adjacent to the bustling, yet calm Kailua Kona town; Kona Shores awaits. The one bedroom, one bath condo offers a private lanai for outdoor seating and a full kitchen to prepare fresh foods that can be picked up from the local farmers market daily. Come and enjoy scenery that will take your breathe away! The unit has Handicap accessible countertops. A washer and dryer included in the unit. Easy walk out to the pool and oceanfront from the footsteps of your private lanai. Private Community Pool. Key hanging in unit for access.

Check rates on Whimstay →

No. 13

Spacious Lanai and Ocean Access - Stunning Hawaiian Getaway

Condo

1 bedroom sleeps 4 private pool about $124 a night

Oceanfront Complex Kona Condo w/ Lanai + Pool. Kona Isle B22 Relax steps from the ocean in this updated Kona Isle condo Enjoy a spacious lanai, in-unit washer/dryer, and easy island living Perfect for couples or small families exploring Kailua-Kona Kona Isle B22 offers a comfortable and convenient home base in one of Kona's most loved oceanfront communities. This updated one-bedroom condo features a queen bed, sofa sleeper, in-unit washer/dryer, and a spacious lanai, perfect for relaxing after a day at the beach. Located along Ali'i Drive, you're just minutes from Kailua-Kona town, dining, shopping, and snorkeling.

Check rates on Whimstay →

No. 14

Ocean View and Refreshing Pool - Stunning Oceanfront Sanctuary

Condo

1 bedroom sleeps 4 private pool about $126 a night

Aliʻi Drive Condo w/ Ocean Views + Full A/C. Kona Isle B38 Enjoy ocean views, full air conditioning, and a top-floor corner location at Kona Isle B38. Located in an oceanfront complex on Aliʻi Drive, this updated one-bedroom condo offers added privacy, cooling comfort, and easy access to the shoreline just steps away. Why Guests Love This Condo Top-floor corner unit for added privacy and light Ocean views from your private lanai Fully air-conditioned (mini splits in living room + bedroom) King bed + sofa sleeper (sleeps up to 4) Updated kitchen + in-unit washer/dryer Oceanfront pool, BBQ area, and tropical grounds The Space This bright and comfortable condo has been updated for easy island...

Check rates on Whimstay →

No. 15

Breathtaking Views and Saltwater Pool - Spectacular Oceanfront Retreat

Condo

2 bedroom sleeps 4 private pool about $128 a night

Kona by the Sea 315 is a roomy 2 bedroom 2-bath unit with all the amenities that you will need, including CENTRAL AC, full-size washer/dryer and high speed wifi. This rental requires a minimum 30-day reservation. No smoking. No pets. Free parking for one vehicle. Registration is a must. Additional parking may be purchased at the front desk. Kona by the Sea is an oceanfront property. This spacious suite is a 2 bedroom - 2 bath well-lit condo that has seen many recent improvements, including upgraded furnishings. Enjoy a great view of the ocean and pool. An elevator makes for easy access from the ground floor.

Check rates on Whimstay →

No. 16

Oceanfront Pool and Charming Amenities - Stunning Coastal Retreat

Condo

1 bedroom sleeps 4 private pool about $128 a night

Kona Reef unit #B33: This 758 sq. ft. vacation rental places you right next to one of the few white sand beaches in Kona, Honl’s Beach, and just a short walk to charming Kailua-Kona town. Unit B33 includes a flat screen TV, DVD player, washer/dryer, and full kitchen with 4-burner stove/oven, microwave, dishwasher, coffee maker, refrigerator, and more. Sleeps up to 4 in 1 king bed and 1 sofa bed. Fringing a sandy beach park and within easy walking distance of Kailua-Kona, Kona Reef Resort welcomes you to sunny days and gorgeous sunsets on Hawaii Island’s west shore. It’s the easy life with an oceanfront swimming pool, jet spa, and poolside cabana with grills.

Check rates on Whimstay →

No. 17

Private Lanai and Poolside Cabana - Gorgeous Oceanfront Escape

Condo

1 bedroom sleeps 4 private pool about $128 a night

Located just a short walk from historic Kailua-Kona washer/dryer, flat screen TV, WiFi, and fully furnished private lanai add a touch of extra comfort for your stay. Sleeps up to four guests in one king and one sofa bed. Town, this spacious 630 sq. ft. vacation condo offers all the comforts of home for your vacation. Take in relaxing views of adjacent Honl’s Beach Park from your fully furnished lanai and enjoy our unit’s many conveniences including air conditioning and ceiling fans, washer/dryer, WiFi, flat screen TV, fully equipped kitchen with microwave, full-sized refrigerator, range/oven, appliances, and dishwasher. Sleeps up to four guests in one king and one sofa bed.

Check rates on Whimstay →

No. 18

Tropical Garden and Cozy Lanai - Charming Island Retreat

Condo

1 bedroom sleeps 2 private pool about $130 a night

Garden View Kona Condo. A/C, Pools, Walk to Ocean Relax in a peaceful garden-view Kona condo Central A/C, private lanai, and island comfort Oceanfront pools + minutes to downtown Kona Welcome to Casa de Emdeko 232, your relaxing island escape on scenic Aliʻi Drive. This one-bedroom condo offers a peaceful garden and mountain-view setting with central air conditioning and a private lanai, perfect for unwinding after a day of Big Island adventures. Spend your days exploring nearby beaches, snorkeling spots, and Kona town, then return home to enjoy sunset views from the oceanfront common areas.

Check rates on Whimstay →

No. 19

Oceanfront Saltwater Pool and Garden Retreat - Inviting Tropical Haven

Condo

1 bedroom sleeps 2 private pool about $133 a night

Garden View Kona Condo. A/C, Pools, Walk to Ocean Relax, reconnect, and unwind in this beautifully remodeled Kona condo Garden views, A/C, and steps to oceanfront sunsets Perfect couples escape along scenic Aliʻi Drive Casa de Emdeko 124 is a beautifully remodeled 1-bedroom, 1-bath condo designed for a peaceful and romantic Big Island getaway. Located in a gated oceanfront complex along Aliʻi Drive, this garden-view retreat offers the perfect balance of comfort, style, and location. Enjoy air conditioning, a California king bed, a private lanai, and easy access to two pools, oceanfront lounging areas, and Kona's stunning sunsets.

Check rates on Whimstay →

No. 20

Oceanfront Swimming Pool and Sandy Beach - Stunning Coastal Sanctuary

Condo

1 bedroom sleeps 3 private pool about $135 a night

vrKCV - Kona Isle C31, Professionally Managed. Oceanfront Kona Isle Condo C31. Top Floor Corner Unit with AC & Partial Ocean View Wake up to island breezes and partial ocean views at Kona Isle C31, a top-floor corner condo located along scenic Aliʻi Drive in Kailua-Kona. This comfortable one-bedroom retreat offers excellent airflow, updated cooling with ductless mini-split AC, and a peaceful oceanfront setting just minutes from downtown Kona. Start your day with Kona coffee on the lanai while looking toward Hualālai. Spend your afternoons snorkeling nearby beaches, exploring local shops, or relaxing on the oceanfront lawn as waves roll in along the shoreline.

Check rates on Whimstay →

No. 21

Oceanfront Lounge and Solar-Heated Swimming Pool - Charming Island Retreat

Condo

1 bedroom sleeps 4 private pool about $136 a night

vrKCV - Kona Isle B5, Professionally Managed. Ground Floor Kailua-Kona Condo Steps from Oceanfront Pool. Kona Isle B5 Welcome to Kona Isle B5, a comfortable ground-floor Kailua-Kona vacation rental located in the oceanfront Kona Isle complex on scenic Ali'i Drive. Just steps from the oceanfront pool, lounge area, and barbecue pavilion, this charming island retreat offers convenient access to the best amenities in the complex while providing a peaceful tropical courtyard setting. The private lanai opens directly to the beautifully landscaped courtyard, allowing you to enjoy Kona's warm breezes and lush garden surroundings.

Check rates on Whimstay →

No. 22

Oceanfront Getaway with Saltwater Pool and Garden Views - Stunning Retreat

Condo

1 bedroom sleeps 4 private pool about $137 a night

Casa De Emdeko 222 by the property manager is a deluxe, one-bedroom oceanfront condominium with miles of coastline views. A perfect blend of efficiency and comfort, this unit features complimentary Wifi, as well as central air conditioning and ceiling fans throughout. The fully equipped kitchen is the perfect space to prepare your favorite meal or snack. The living room is located a few steps from the kitchen and is furnished with a plush, queen-sized sleeper sofa to comfortably accommodate additional guests. Access the lanai from the living room which features a garden and partial ocean views.

Check rates on Whimstay →

No. 23

Spacious Lanai and Stunning Views - Breathtaking Oceanfront Retreat

Condo

1 bedroom sleeps 2 private pool about $140 a night

Top-Floor Oceanfront Kona Condo. Panoramic Sunset Views + A/C Wake up to the sound of the ocean and unwind with unforgettable sunsets from this top-floor corner condo on Aliʻi Drive. With sweeping 180-degree ocean views, a private lanai, and air conditioning in both the living room and bedroom, Kona Riviera Villas 206 is perfectly suited for couples looking for a scenic and comfortable Big Island stay.

Check rates on Whimstay →

No. 24

Oceanfront Oasis with Pool and Coastal Views - Stunning Hawaiian Retreat

Condo

1 bedroom sleeps 4 private pool about $151 a night

Casa De Emdeko 235 is a one-bedroom, one-bathroom non-smoking condominium within walking distance of downtown Kailua-Kona. This non-smoking oceanfront property features complimentary Wifi and is conveniently situated on Ali'i Drive, with miles of coastline views. Casa De Emdeko 235 is a comfortable, newly-remodeled unit only three doors from the ocean. It features complimentary Wifi, as well as central air conditioning and ceiling fans throughout. The fully equipped kitchen at Casa De Emdeko 235 is stocked with a high-end blender and coffee maker, as well as all of the essentials necessary to prepare your favorite meal.

Check rates on Whimstay →

No. 25

Oceanfront Pool and Scenic Lanai - Charming Coastal Retreat

Condo

1 bedroom sleeps 4 private pool about $155 a night

E Komo Mai to Hale Lani a charming oceanfront condo with AC and easy access to Kona’s dining, shops, and beaches. Near town, it’s perfect for anyone who wants to be close to the action while enjoying peaceful ocean views and the soothing sound of the waves Welcome to Hale Lani, a serene 1-bedroom, 1-bath oceanfront condo with bedroom A/C in the boutique Kona Riviera Villas on Ali‘i Drive. Located directly in front of the surf break, this ground-floor unit opens onto the oceanfront pool deck for effortless access to a morning swim, an afternoon sunbath, or a sunset barbecue.

Check rates on Whimstay →

No. 26

Oceanfront Pool and Spa - Stunning Coastal Sanctuary

Condo

1 bedroom sleeps 4 private pool about $166 a night

vrKCV - Sea Village 1103, Professionally Managed Oceanfront Ground Floor Kona Condo. Lanai Over Water Wake up just steps from the ocean at this ground-floor Kona condo. Private lanai perched directly over the water with unobstructed views. Walk to beaches, relax by the oceanfront pool, and enjoy true island living. Sea Village 1103 offers a rare ground-floor oceanfront experience with a spacious lanai directly above the Pacific. Enjoy the sounds of the waves, refreshing ocean breezes, and stunning coastline views throughout your stay. Perfect for couples or small families, this comfortable condo is just minutes from downtown Kailua-Kona, beaches, and local dining.

Check rates on Whimstay →

No. 27

Oceanview and Resort Amenities - Gorgeous Coastal Escape

Condo

2 bedroom sleeps 4 private pool about $169 a night

This is your beach vacation headquarters. Kona Makai is an oceanfront resort community set right on Alii Drive near Kona's best boogie boarding and snorkeling beaches and surf breaks. A gorgeous, oceanside swimming pool, hot tub, barbecue area, two tennis courts and a small exercise facility are all on site. Your beautifully remodeled condo sleeps four with a comfortable California king bed in the master bedroom and a queen bed in the upstairs loft. The master bedroom is spacious and comfortable and it opens to its own lanai. The bathroom is bright and stylish with a dual sink vanity and a glass enclosed shower.

Check rates on Whimstay →

No. 28

Oceanfront Condo with Loft and Resort Amenities - Stunning Coastal Retreat

Condo

1 bedroom sleeps 4 private pool about $170 a night

From panoramic ocean views to breezy lanai dining, the details below show how Kona Makai 6303 brings Kailua-Kona’s coastal charm to life. Living & Dining Step inside to an airy living room with vaulted ceilings, island-inspired decor, and leather sofas. A flat-screen TV with cable and WiFi keeps you connected, while glass doors open to the lanai where ocean breezes, crashing waves & Hawaiian sunsets. Chef Ready Kitchen The upgraded kitchen is furnished with full size appliances, ample cabinetry, coffee and breakfast bar for casual dining. Fully stocked with all culinary essentials. Start your day with a Kona brew and prep for an evening cookout at surfside barbecues.

Check rates on Whimstay →

No. 29

Oceanfront Swimming Pool and Gourmet Kitchen - Stunning Island Retreat

Condo

1 bedroom sleeps 4 private pool about $173 a night

Kona Reef unit #D01 on the ground-floor: Walk from the private lanai to the ocean’s edge for a beautiful Kona sunset. This open-design, air-conditioned 758 sq. ft. retreat invites you to prep meals in the gourmet kitchen with breakfast bar. Other touches include ceiling fans, a washer/dryer, and WiFi. Sleeps 4 in 1 King and 1 Sofa bed. Fringing a sandy beach park and within easy walking distance of Kailua-Kona, Kona Reef Resort welcomes you to sunny days and gorgeous sunsets on Hawaii Island’s west shore. It’s the easy life with an oceanfront swimming pool, jet spa, and poolside cabana with grills. Minimum age to book this property is: 18

Check rates on Whimstay →

No. 30

Kona Isle B31

Vacation Home

1 bedroom sleeps 4 Beachfront private pool about $175 a night

Kona Isle B31 offers comfortable beachfront accommodation in Kailua-Kona.

Check rates on Booking.com →

No. 31

Oceanfront Location and Private Lanai - Stunning Hawaiian Escape

Condo

1 bedroom sleeps 4 about $175 a night

vrKCV - Kona Isle D23. Professionally managed Oceanfront Kona Condo. Remodeled. Sunset Views. Kona Isle D23 Wake up to the sound of the ocean and spend your evenings watching unforgettable Kona sunsets from your private lanai. This newly remodeled second-floor oceanfront condo at Kona Isle offers front-row views of the Pacific, modern comforts, and a peaceful oceanfront setting just minutes from downtown Kailua-Kona. Whether you're relaxing by the water, exploring the island, or enjoying dinner overlooking the coastline, Kona Isle D23 is the perfect place to experience the Big Island.

Check rates on Whimstay →

No. 32

Oceanfront Pool and Hot Tub - Charming Tropical Escape

Condo

1 bedroom sleeps 2 private pool about $176 a night

Oceanfront Ali'i Drive Condo Steps from Honl's Beach. Kona Reef Wake up just steps from the shoreline at Kona Reef, a popular oceanfront property on scenic Ali'i Drive in Kailua-Kona. Located next to Honl's Beach (Waiʻaha Bay Beach Park) and less than half a mile from downtown Kona, this property places you close to oceanfront dining, shopping, local markets, and Big Island activities. Spend your days exploring the coastline, watching surfers and bodyboarders at the beach next door, or relaxing by the oceanfront pool and hot tub. In the evening, enjoy Kona's famous sunsets and grill dinner at the community BBQ area. Why Guests Love Kona Reef. Oceanfront location on Ali'i Drive.

Check rates on Whimstay →

No. 33

Panoramic Sunset Views and Easy Access - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 3 private pool about $177 a night

vrKCV - Sea Village 4104, Professionally Managed True Oceanfront Kona Condo. Ground Floor, No Stairs. Sunset Views Front-row sunsets. Unobstructed ocean views. Easy ground-floor access. Welcome to the “Turtle House” at Sea Village, your true oceanfront escape overlooking Kailua Bay. This elevated ground-floor condo offers sweeping 180° views, the sound of crashing waves, and effortless access with no stairs. One of the largest 1-bedroom layouts on Ali'i Drive, it's the perfect place to relax, dine, and soak in the beauty of Kona. Why Guests Love This Condo True oceanfront with panoramic views Ground-floor unit, no stairs Spacious lanai for sunset dining Larger 1BR floor plan (approx.

Check rates on Whimstay →

No. 34

Private Balcony and Full Kitchen Amenities - Elegant Coastal Retreat

Condo

1 bedroom sleeps 4 private pool about $177 a night

Beautiful condominium situated on 16 acres of a secluded oceanfront lava flow overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscapes. Golfers, families and outdoor enthusiasts will enjoy snorkeling, golf and deep-sea fishing nearby Kanaloa at Kona Ocean View 1 Bedroom 1 Bath. Kanaloa at Kona is located at 78-, Kailua-Kona, HI 96740. Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware. Welcome essentials kit includes coffee, tea, sugar, creamer, dish soap, sponge, paper towels, dishwasher detergent, and laundry detergent. Bedroom has 1 king bed. Shower or Shower/tub combination.

Check rates on Whimstay →

No. 35

Oceanfront Kailua-Kona Islander Studio w/ Lanai!

Entire condo

sleeps 2 shared pool about $179 a night

Switch into island time the second you land on the Big Island of Hawaii and get settled into your tropical home-away-from-home in the Kona Islander Inn. This Kailua-Kona vacation rental studio features 1 bathroom, a well-equipped kitchenette, a private lanai, and a community pool and hot tub.You’ll be right downtown within walking distance of beaches, restaurants, shops and the Farmer’s Market. Plan a sunset cruise, swim with dolphins, go snorkeling or attend a luau during your time in paradise! The space TA- -01. GE- -01. Window A/C Unit. Free WiFi.

Check rates on Whimstay →

No. 36

Ocean View and Pool Access - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 private pool about $180 a night

vrKCV - Kona Isle D1, Professionally Managed. Ocean Views, Oceanfront Pool & Sunset Lanai. Kona Isle D1 Enjoy the beauty of the Kona Coast from this comfortable one-bedroom, one-bath ocean-view condo at Kona Isle. Spend your mornings sipping coffee on the private lanai, your afternoons exploring nearby beaches, and your evenings watching colorful sunsets over the Pacific. Perfect for couples, Kona Isle D1 offers a peaceful oceanfront setting just minutes from Historic Kailua Village, with everything you need for a memorable Hawaiʻi Island vacation.

Check rates on Whimstay →

View all 44 waterfront rentals in Big Island ↓

No. 37

Elegant Oceanfront Retreat with Pool and Tennis Courts - Exquisite Escape

Condo

2 bedroom sleeps 6 private pool about $185 a night

From its ground-floor oceanfront setting and private lanai to renovated baths, the details below show how Keauhou Kona Surf & Racquet 1104 supports easy Kona days. Living & Dining The open-concept living area welcomes you with bright, airy spaces and island-inspired décor. Sliding glass doors open to your private lanai, where tropical breezes and ocean views set the tone for relaxation. the property manager on plush sofas for movie nights on the Smart TV or share meals at the dining table for five after a day of adventure.

Check rates on Whimstay →

No. 38

Private Balcony and Full Kitchen Amenities - Charming Oasis

Condo

1 bedroom sleeps 4 private pool about $186 a night

Beautiful condominium situated on 16 acres of a secluded oceanfront property overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscape. Kanaloa at Kona Fairway View 1 Bedroom 1 Bath. Kanaloa at Kona is located at 78-, Kailua-Kona, HI 96740. Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware. Welcome essentials kit includes coffee, tea, sugar, creamer, dish soap, sponge, paper towels, dishwasher detergent, and laundry detergent. Bedroom has 1 king bed. Shower. Bath amenities include conditioner/shampoo, soap & hair dryer. Living area with queen sofa bed.

Check rates on Whimstay →

No. 39

Oceanfront Lanai and Snorkeling Gear - Stunning Coastal Escape

Condo

1 bedroom sleeps 4 about $187 a night

This newly remodeled oceanfront condo located right in the heart of Kailua Kona has everything you need to make your vacation complete. This one bedroom is fully furnished with snorkeling gear, boogie boards and a kitchen that is a chefs delight. A king size bed in the bedroom and a fold out tempurpedic Queen bed in the living room make this condo a vacationers delight. A lanai that overlooks the bay so you can dine watching the sunsets or enjoy sipping a cup of Kona Coffee while watching dolphins and whales splashing around right in front of you. This unit can be rented with AC at an additional charge of $15 per day, please inquire with a reservation agent.

Check rates on Whimstay →

No. 40

Oceanfront Location and Private Lanai - Breathtaking Island Haven

Condo

2 bedroom sleeps 4 private pool about $189 a night

vrKCV - Alii Villas 131, Professionally Managed. Oceanfront Bliss - Stunning Kailua-Kona Oceanfront Condo with Panoramic Coastline Views Wake up to sweeping ocean views and the sparkling coastline of Kailua-Kona at Oceanfront Bliss, a beautifully updated 2-bedroom, 2-bathroom oceanfront condo on Ali'i Drive. From the moment you step inside, wall-to-wall ocean views welcome you, creating a serene island atmosphere throughout the home. Watch waves roll across Kailua Bay from the private lanai, enjoy unforgettable Kona sunsets, and take in the twinkling lights of town at night.

Check rates on Whimstay →

Booking.com

Hotels, beach houses & apartments in Big Island.

Browse on Booking.com →

Affiliate link.

No. 41

Breathtaking Views and Resort Amenities - Spectacular Oceanfront Escape

Condo

1 bedroom sleeps 4 private pool about $190 a night

vrKCV - Sea Village 4312, Professionally Managed Oceanfront Kona Condo. Top Floor Views & Lanai Top-floor oceanfront condo with sweeping Kailua Bay views Watch dolphins, whales & sunsets from your private lanai Walk to town, relax by the oceanfront pool & unwind in Kona Overview Experience classic Kona oceanfront living at Sea Village 4312, a top-floor 1-bedroom condo with breathtaking 180-degree views of the Pacific. Start your day with coffee on the lanai, spot dolphins offshore, and end with vibrant Hawaiian sunsets. Located along Aliʻi Drive just one mile from downtown Kailua-Kona, this condo offers the perfect balance of relaxation and convenience.

Check rates on Whimstay →

No. 42

Oceanfront Pool and Expansive Lanai - Stunning Hawaiian Retreat

Condo

1 bedroom sleeps 3 private pool about $193 a night

Welcome to Hale Kona Kai 412, a stunning oceanfront condo at the top corner of the building that promises an unforgettable getaway in the heart of Kailua Kona. This completely remodeled modern unit is perched on the top floor, offering breathtaking views of the Pacific Ocean from its expansive wraparound lanai, where you can soak in the beauty of the Hawaiian sunsets. This one-bedroom, one-bathroom retreat comfortably accommodates two guests. The spacious bedroom features a luxurious king-sized bed, ensuring a restful night's sleep after a day of adventure. POOL NOTICE: The pool will be closed from June 21 - July 2, due to exterior work being completed close to the pool area.

Check rates on Whimstay →

No. 43

Condo with Private Beach Club Access & Pool

Townhouse

2 bedroom sleeps 4 private pool about $195 a night

Palm Villas I-2 is a spacious two-bedroom, two-bath condo located on the ground level of a quiet six-plex building in the Palm Villas at Mauna Lani. With approximately 1,100 square feet of living space, this home comfortably sleeps up to four guests. The main bedroom features a queen bed, en-suite bathroom, and access to the private lanai. The second bedroom is equipped with one full and one twin bed, and a second full bathroom with a combination shower and tub is conveniently located just off the hallway. The gourmet kitchen includes granite countertops, stainless steel appliances, and a wine fridge, and is fully stocked with everything you need to prepare meals at home.

Check rates on Whimstay →

No. 44

Oceanfront Lanai and Pool - Stunning Hawaiian Escape

Condo

1 bedroom sleeps 2 private pool about $198 a night

vrKCV - Kona Reef A32, Professionally Managed Top-Floor Oceanfront Kona Condo. Walk to Town. AC. Kona Reef A32 Wake up to panoramic Pacific Ocean views at Kona Reef A32, a beautifully remodeled top-floor oceanfront condo just steps from the shoreline. Watch surfers ride the waves, enjoy breathtaking sunsets from your private lanai, and stroll just minutes to Kona Town for dining, shopping, and island adventures. Perfect for couples or solo travelers seeking a relaxing Kona getaway with incredible views and unbeatable walkability. Why Guests Love This Condo. Top-floor oceanfront location with panoramic views. Private lanai just feet from the water.

Check rates on Whimstay →

On the water

Rent a boat in Big Island.

Browse Boat Rentals →

Affiliate link.