Vacation rentals with a pool in Hawaiian Islands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hawaiian Islands

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Pāhoa

4.93 out of 5 average rating, 450 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.

Superhost

Cottage in Molokai

4.95 out of 5 average rating, 108 reviews

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

Enjoy stunning sunset views of the Pacific Ocean, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, oceanfront cottage with a large covered lanai. This No Smoking two-Level cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore or just unplug and relax. You will experience colorful sunsets, breezes, tropical birds, beaches, and breaching whales in the winter.

Guest favorite

Villa in Pāhoa

4.94 out of 5 average rating, 103 reviews

Lava Flow House Pool Ocean View Kehena Beach w A/C

This luxurious modernist masterpiece with swimming pool and ocean view, sits in a serene setting in the untouched area of the Puna Coast on the Big Island of Hawaii. If you love great design and style, fantastic tropical weather, rugged yet lush landscapes, blue ocean, and relaxation, then you will love this place for your next vacation. The unique combination is a stunning contrast of rugged landscape and sharp minimalist architecture. This is a shared family home with a Main house and Studio.

Top guest favorite

Condo in Princeville

4.99 out of 5 average rating, 327 reviews

~The Surfshack~ with breathtaking ocean views!!

A modern surf oasis nestled on an overlook with panoramic ocean views, stunning sunsets, and the famous Bali Hai. We are featured in the June issue Sunset Magazine. You'll never want to leave this modern Hawaiian styled 2 bedroom, 2 bath condo. We have everything you’ll need and want for the most relaxing stay of your island vacation and only steps away from food, drinks, the pool and the beach. Whale watch from the lana'i in the winter, or snorkel our beautiful Hideaways beach in the summer.

Guest favorite

Cabin in Maui

4.97 out of 5 average rating, 222 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✔

Superhost

Condo in Waianae

4.97 out of 5 average rating, 295 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Top guest favorite

Condo in Lahaina

4.99 out of 5 average rating, 133 reviews

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi

Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

Top guest favorite

Condo in Princeville

4.98 out of 5 average rating, 291 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!

Top guest favorite

Guesthouse in Hakalau

4.96 out of 5 average rating, 251 reviews

Oceanfront Estate Retreat 1 - Carriage w/ Horses

Experience unmatched luxury in a one-bedroom apartment of a world class, $10+M gated oceanfront estate perched on a dramatic cliff edge with a pool. Wake up to breathtaking sunrises, panoramic ocean views in your spacious apartment that features a private lanai, separate living and sleeping rooms, full kitchen, bathroom with walk-in rainfall shower, bidet, and custom furnishings. This property offers privacy, elegance, and stunning surroundings for singles, couples, or honeymooners.

Guest favorite

Cottage in Hanalei

4.94 out of 5 average rating, 359 reviews

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a secluded romantic haven nestled on an acre of lush gardens in Kauai’s breathtaking Wainiha River Valley. Perched on a bluff with panoramic valley views, this retreat offers tranquility and luxury. Unwind by your private pool and spa, surrounded by vibrant tropical flora, where nature creates an atmosphere of enchantment. Just a short drive away, explore some of the world’s most stunning beaches. Let this serene paradise immerse you in romance and blissful relaxation

Top guest favorite

Condo in Maunaloa

4.98 out of 5 average rating, 256 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.

Guest favorite

Home in Kihei

4.96 out of 5 average rating, 440 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003