
Holiday 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.

Private Pool - 180° Ocean View - Minutes to Beach
WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

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.

Panoramic luxury beachside condo in paradise A/C
Oceanside Paradise. 180 degree Ocean views. Large private Lanai with breathtaking 180 degree views inside and out. See dolphins, whales, turtles, rainbows & amazing sunrises. Steps from beach & centrally located on the famous Coconut Coast & steps from the Lae Nani beach. Beach chairs & gear included. Beautifully remodeled with an open, custom kitchen/baths & vaulted ceiling. Boasts double master suites, Beautiful Pool, BBQ area, beach access, A/C, washer/dryer & private covered parking.

★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✔

Exceptional Oceanview Home - Pool & Stunning View
Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

Tropical Oasis: Heated Pool, Waterfall, Ocean View
Welcome to Nakukui Hale, your own private Hawaiian sanctuary — a beautifully designed estate for up to 8 guests in a gated community. A resort-style waterfall spills over lava rock into a deep blue-tiled heated pool. Wander the lush landscape, listen to colorful birds sing, and unwind in the elevated private gazebo as the sun sets over the Pacific. Just minutes from Ali'i Drive, Magic Sands Beach, Ironman Pier and the best restaurants in Kona town. This is Hawaii living at its absolute finest.

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views
Relax & enjoy stunning ocean & sunset views, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, two-story oceanfront cottage with a large covered lanai. This no-smoking 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 unplug & relax. You will enjoy blue ocean & beach views, colorful sunsets, breezes, tropical birds, waves, and whales in the winter.

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.

Stunning Serene Bali Retreat [Pool/AC/Ocean View]
Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai/Balinese architecture, hand-carved wood everywhere, and ample windows/skylights that showcase the beauty of the Big Island. The kitchen/living rooms connect to the owner's retreat via covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a quiet atmosphere and cooler temps than busy downtown while not being far from the action.

Peace of Paradise at Kepuhi Beach Resort #2224
(TA#086363955201) Molokai oceanfront condo. View amazing sunsets, beautiful grounds and occasional whale sightings from our 2nd floor lanai. Updated with custom art, fresh linens, full size futon, gel topper for the king size bed, fully equipped kitchen and vanity areas. Ceiling fans and trade winds will keep you cool and comfortable. Washer/dryer, stereo, flat screen TV, free Wi-Fi all add to your comfort. Spend idyllic days lounging at the beach/pool or off on an island adventure!

Maui Full Oceanfront Paradise
Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

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
Popular amenities for Hawaiian Islands rentals with a pool
House rentals with a pool

HAVEN: Poolside Sanctuary with Heavenly Views

Million Dollar View | Sunsets & Aloha

Puna Rainforest Retreat Hotspring Rainbow Cottage

Romantic Dodecagon Retreat Near a Black Sand Beach

Victoria Loop! Private Pool + AC & Waterfall Views

Exceptional Upcountry Villa, breathtaking views!

Kula Jewel - Pool, Hot Tub & Awesome Views!

4 BR, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng
Apartment rentals with a pool

~The Surfshack~ with breathtaking ocean views!!

Spectacular Oceanfront Condo, A/C + Sunset Views!

Sea and Sky Kauai, an Oceanfront Penthouse dream

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

Brand New Luxurious Condo on North Shore Kauai

Million $ View on Gorgeous Secluded Beach!

Amazing Waikiki Beach Views!!

Jewel of the Pacific. Seaside condo at Sealodge
Other holiday rentals with a pool

Jasmine Suite Farm Stay in Haiku on Road to Hana

Ocean View Hideaway

Pineapple Palace~Stunning Ocean Views~Private Pool

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

32F-Penthouse Pacific Monarch Studio-Ocean View

One bedroom suite, private pool and ocean views.

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

Stylish beach house a short walk to Koloa fun!
Destinations to explore
- Resort rentals Hawaiian Islands
- Rentals with an accessible-height bed Hawaiian Islands
- Cabin rentals Hawaiian Islands
- Rentals with beach access Hawaiian Islands
- Cottage rentals Hawaiian Islands
- Nature eco lodge rentals Hawaiian Islands
- Hotel rooms Hawaiian Islands
- Beachfront rentals Hawaiian Islands
- Family-friendly rentals Hawaiian Islands
- Rentals with an EV charger Hawaiian Islands
- Aparthotel rentals Hawaiian Islands
- Tiny house rentals Hawaiian Islands
- Rentals with a firepit Hawaiian Islands
- Rentals with a cinema Hawaiian Islands
- Rentals with a sauna Hawaiian Islands
- Rentals with a beach view Hawaiian Islands
- Tent rentals Hawaiian Islands
- Rentals with a balcony Hawaiian Islands
- Farm stay rentals Hawaiian Islands
- Guest house rentals Hawaiian Islands
- Flat rentals Hawaiian Islands
- Rentals with lake access Hawaiian Islands
- Rentals with a fireplace Hawaiian Islands
- Rentals with outdoor seating Hawaiian Islands
- Rentals with a patio Hawaiian Islands
- Rentals with breakfast Hawaiian Islands
- Waterfront rentals Hawaiian Islands
- Private suite rentals Hawaiian Islands
- Smoking-friendly rentals Hawaiian Islands
- Serviced apartment rentals Hawaiian Islands
- Treehouse rentals Hawaiian Islands
- Apartment rentals Hawaiian Islands
- House rentals Hawaiian Islands
- Bed and breakfasts Hawaiian Islands
- Motorhome rentals Hawaiian Islands
- Holiday home rentals Hawaiian Islands
- Villa rentals Hawaiian Islands
- Townhouse rentals Hawaiian Islands
- Boutique hotels Hawaiian Islands
- Rentals with a hot tub Hawaiian Islands
- Hostel rentals Hawaiian Islands
- Luxury rentals Hawaiian Islands
- Pet-friendly rentals Hawaiian Islands
- Loft rentals Hawaiian Islands
- Rentals with a washing machine and dryer Hawaiian Islands
- Rentals with an accessible-height toilet Hawaiian Islands
- Rentals with a kayak Hawaiian Islands
- Fitness-friendly rentals Hawaiian Islands





