Holiday rentals with a pool in Hawaii

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hawaii

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Pāhoa

4.93 out of 5 average rating, 371 reviews

Romantic Dodecagon Retreat Near a Black Sand Beach

Feel the tropical vibe as sunlight pours into a fun and unique 12-sided home with a central dome skylight and vaulted ceilings. Casual, stylish furnishings, playful textiles, beautiful Balinese hardwood floors, a well-appointed kitchen and a deep, jetted tub with an oversized rain-showerhead create an inviting interior. Outside is the irresistible allure of your own private pool surrounded by lush greenery made complete with a soothing outdoor shower. Enjoy exotic flowers, fruit trees, native plants, and a beautiful lava-rock wall landscaped to give you complete privacy. Close to Kehena Beach! The unique 12-sided architecture includes high-pitched ceilings, Balinese hardwood floors, interior cedar siding w/ Redwood rafters, four screened doors and several screened windows and two Haiku ceiling fans to offer plenty of air-flow and natural light. A large dome skylight offers views of palm trees during the day and the stars at night. With a beautiful, fully-outfitted kitchen that includes spacious, granite countertops, a six-burner gas stove, oven, large refrigerator and a central island, there is plenty of room to prepare meals and to entertain. The well-appointed furniture includes a comfortable day bed, an over-sized, cozy papasan, a custom, artisanal desk, and an organic latex queen-sized bed with 100% cotton, high-thread count sheets. Pool, outdoor shower, and laundry facilities. Dr. Bronner's Liquid Soap, Shikai Shampoo and Conditioner provided. Indoor jet-tub with oversized, rain-type shower-head. Manager (not on property) is available for assistance nearby. Pool guy comes every four days, Mondays & Thursdays around 3pm to maintain pool (will give advance notice). ‘Mahalo Kai’ is immaculately landscaped and surrounded by coconut, mango, ‘soursop’, avocado, papaya, and banana trees. ‘Kehena’ Beach, located just 2 blocks away, is a beautiful black-sand (clothing-optional) beach and is ideal for sunbathing, exploring, picnics, swimming, and body-surfing. Activities include the fun-filled Wed. Night Market at Uncle Robert’s in Kalapana, nearby Farmer's Markets and driving or biking the gorgeous "Red Road": one of THE most scenic coastal roads in the world! There is an island bus. A rental car is recommended. The pool is a 30-foot (10m) round pool with an average depth of 4 feet (1.3m) and, while temperatures can vary depending on weather, it has an average temperature of 82°F (27.8°C). It is typically warmer in the Summer months and a touch cooler in the Winter months. It is tended every three to four days by our pool caretaker. Sorry, but we do not offer a dishwasher for guest use. Please note that cell phone reception tends to be weak at our home but the WiFi is excellent and there is a landline (you will need a calling card for long distance calls.) Mahalo Kai is just a block from the black sand Kehena Beach and 5 miles from a brand new black sand beach. The natural surroundings feature coconut trees, coffee, tropical fruit, and exotic flowers. Activities include bike trails and a night market.

9–16 Nov

$350 SGD per night

Guest favourite

Place to stay in Pāhoa

4.94 out of 5 average rating, 108 reviews

TROPICAL GARDEN OASIS

8 minutes from shopping & restaurants in historic Pahoa, enjoy the setting of this romantic spot in nature. A sweet getaway surrounded by lush tropical landscaping. Fall asleep to the Milky Way & nature sounds. Your private cabin has a comfy queen size bed & tropical decor. Take a dip in a deep azure pool with a cabana & Bali gazebo. A sexy out door shower built for two has an open view to the garden & is adjoining a private seating area w a lily & koi pond. BLISS! 🌸🌈INSTABOOK TODAY! 🌺🌴

12–19 Aug

$149 SGD per night

Guest favourite

Cabin in Maui

4.98 out of 5 average rating, 171 reviews

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

14–21 Feb

$1,052 SGD per night

Guest favourite

Apartment in Honolulu

4.89 out of 5 average rating, 246 reviews

Newly Renovated Cozy Home

Experience the charm of our newly renovated studio, legally permitted for your peace of mind. Revel in the modern ambiance featuring wood-like floors, luxurious marble countertops, and a stylishly tiled bathroom. Immaculately maintained for your comfort, the studio boasts SUPER CLEAN interiors and offers FANTASTIC CANAL VIEWS. Conveniently located within walking distance to the famous beaches, shopping malls, delectable dining options, and all your essentials. Your dream getaway begins here!

30 Oct – 6 Nov

$164 SGD per night

Guest favourite

Guest suite in Pāhoa

4.98 out of 5 average rating, 151 reviews

Hale Malama 'Ohana

Unique 850 sqft one bedroom Ohana with ocean views, vaulted ceilings, full kitchen, private lanai, saltwater pool w gazebo, nestled in a stunning 3 acre estate. This ohana has a special history as it was formerly Sea West Studios, a world class recording studio that served Hawaii's premier artists (Crosby Stills & Nash recorded vocals here) who preferred to record in this incredibly peaceful atmosphere. Pele spared this oasis during the 2018 eruption, saving it for your special experience.

13–20 Apr

$156 SGD per night

Guest favourite

Bungalow in Kalaheo

5.0 out of 5 average rating, 101 reviews

Eco Luxe Villa, Infinity Pool

No house should ever be on a hill or on anything. It should be of the hill, belonging to it. Hill and house should live together, each the happier for the other." -- Frank Lloyd Wright Nestled in the Kalaheo hills 20 minutes north from Poipu, this oasis offers modern barefoot luxury with breathtaking views of the lush tropical landscape. The Longhouse has full privacy from the main residence located on the same parcel, it is the place to unplug and unwind, surrounded by nature's beauty.

15–22 Jan

$1,413 SGD per night

Guest favourite

Apartment in Princeville

4.99 out of 5 average rating, 210 reviews

Sea and Sky Kauai, an Oceanfront Penthouse

This modern and newly renovated honeymoon beach retreat has breathtaking panoramic ocean and coastline views. Lounge in the daybed while gazing at the sweeping vista from Anini reef to Kilauea Lighthouse. Some have said "it feels like being on a ship at sea" as they witness whales breaching in the ocean and waves peeling on the reef from this magical location. A rare penthouse unit with high ceilings, views from every room, even the famous Bali Hai from the deck. Truly a couple's dream!

2–9 Sep

$763 SGD per night

Guest favourite

Guest house in Keaau

4.97 out of 5 average rating, 184 reviews

Magical Jungle Cabin with Pool

Nestled in a lush guava tree grove, this tropical sanctuary offers the nature sounds of camping with the comforts of a cozy bungalow. Perfect for a couple's getaway, a personal retreat, or a peaceful place to retire to after a full day of exploring. Wake up with an outdoor rainfall shower, soak up the Hawaiian sunshine while you float in the pool, grill locally caught fish in the kitchenette pavilion (hot plate and BBQ), and stargaze some of the darkest night skies. Primary residence.

14–21 Jun

$210 SGD per night

Superhost

Apartment in Pahala

4.9 out of 5 average rating, 414 reviews

'Âlani Punalu'u Black Sand Beach oceanview retreat

Serene, remote, zen retreat in one of Hawaii's most scenic places: K’au region at Punalu'u Black Sand Beach. It’s a short 1/3 mile walk to the beach, crashing waves, palm trees & flowers, amazing mountain and ocean views, in the countryside of macademia nut & coffee farms. Incredible dark sky with countless stars. A gorgeous 30 minute drive to Volcanoes National Park. Far removed from the hustle of city life, welcome to the most remote inhabited place on the edge of the universe.

13–20 Aug

$239 SGD per night

Guest favourite

Apartment in Princeville

4.98 out of 5 average rating, 128 reviews

Brand New Luxurious Condo on North Shore Kauai

Brand New Listing at the Hanalei Bay Resort. Wake up to breath taking views of the Hanalei bay, waterfalls and the amazing lush green mountains of the garden island. Along with the amazing scenery you will also have access to pools, hot tubs, tennis courts, private beach access, weight room facilities and enjoy live music every night at the Happy Talk Lounge. All of theses activities are just a minutes walk from your front door or enjoy a relaxing golf cart shuttle ride.

13–20 Oct

$778 SGD per night

Superhost

Cottage in Hanalei

4.93 out of 5 average rating, 271 reviews

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a romantic paradise, tucked away on an acre of lush gardens in the dazzling Wainiha River Valley. Perched atop a bluff overlooking the valley, you are immersed in the serenity and opulence of your private pool and spa, surrounded by vibrant colors and lush greenery, creating a truly surreal and romantic atmosphere. Just miles away, discover some of the world's most beautiful beaches. Let this idyllic retreat transport you to a world of pure romance and bliss.

21–28 Dec

$1,077 SGD per night

Guest favourite

Apartment in Maunaloa

4.97 out of 5 average rating, 234 reviews

Sweet Upstairs Corner Ocean View Studio on Molokai

Top floor corner unit at Kepuhi Beach Resort, on the special island of Molokai....in between Maui and Oahu! Vaulted open ceilings, spacious and airy. Completely remodeled and freshly outfitted. Close to beach and ocean-side pool, views of Kaiaka Rock, ocean surf, vivid sunsets. Fully equipped kitchen, luxurious King sized bed. Fast wireless , 40” SmartTV. Perfect setting to unplug, hike or bike the red dirt trails, explore beaches, and experience Molokai fully.

10–17 Jul

$152 SGD per night