
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.

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.

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.

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.

Puna Rainforest Retreat Hotspring Rainbow Cottage
The Rainbow Cottage boasts a breathtaking ocean view from the queen bedroom and lanai. The cottage features a full bathroom and kitchenette containing a range, oven, mini-fridge, and microwave. There's a cozy twin bed for a third guest in the living room. Amenities: pool, two volcanic hot tubs, rainforest trail, garden, orchard, and a peaceful private retreat setting surrounded by nature. The owner lives on the 20-acre property to ensure your stay is perfect in every way. TA-008-365-8240-01

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!

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.

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

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.

Beach 6 Min|Community Pool+Gym|Gated|Mountain View
This four-bedroom retreat in the gated Mauna Olu Estates blends mountain views with local Hawaii design touches - a custom wood bar table and mural in the dining room. It sleeps up to 10 across four bedrooms - a king suite, two queens, and a flexible fourth room with a full bed, trundle, and sleeper sofa. Guests get community pool and gym access plus a private, fenced backyard for grilling. It's an easy fit for a family reunion or multiple families traveling together.

Gorgeous Gated Retreat w Pool Deck Firepit, 1 acre
Enjoy a blissful vacation at the Hawaiian Paradise Beach House. This 3BR/2BA retreat is perfect for groups of 10, offering welcoming spaces both indoor and outdoor to dine and relax in the beautiful Hawaiian weather. Spacious outdoor deck with swimming pool, fire pit, lounge areas. Close to shops, beaches, and the airport, it's a convenient yet peaceful stay. Considerate host nearby. We look forward to welcoming you to our tropical escape!
Popular amenities for Hawaiian Islands rentals with a pool
House rentals with a pool

Kula Jewel - Pool, Hot Tub & Awesome Views!

Private Pool - 180° Ocean View - Minutes to Beach

Ocean, Sunset, Mountain & Celestial Views

HAVEN: Poolside Sanctuary with Heavenly Views

Hamakua Coast Tropical Home

He'e Hideout ~ Top 1% (3 bdr + private studio)

Pool, 6 mins to Beach, Ocean View, H7

Mollie’s Paradise Resort Home & Private Pool
Apartment rentals with a pool

Beachfront Resort, Peaceful Mountain View Studio

Large Corner Unit at Bamboo with Full Kitchen

Lahaina Studio: Beachfront, Mountain View, Hot Tub

Pineapple Paradise at Poipu Crater A/C In Bedrooms

Modern 1 Bedroom Condo in Downtown Honolulu

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

OCEANFRONt 3+2.5 FREE AC BeachGear

#Stunning Ocean / Diamond Head Corner Unit 32nd Fl
Other holiday rentals with a pool

Oceanfront Estate Retreat 2 - Solar w/ Horses

Maui Full Oceanfront Paradise

Seahorse Luxury Suite at Seaspray Ocean View

Pineapple Palace~Stunning Ocean Views~Private Pool

Oceanfront! Outstanding 2BR/2BA w Pool & Hot Tub

Ocean View Hideaway

Private Poolside Oasis & Ocean Views

Best Kept Secret on Oahu! and WE ARE LICENSED!!!
Destinations to explore
- Cottage rentals Hawaiian Islands
- Cabin rentals Hawaiian Islands
- Rentals with beach access Hawaiian Islands
- Nature eco lodge rentals Hawaiian Islands
- Hotel rooms Hawaiian Islands
- Beachfront rentals Hawaiian Islands
- Rentals with an accessible-height bed Hawaiian Islands
- Resort rentals Hawaiian Islands
- Family-friendly rentals Hawaiian Islands
- Aparthotel rentals Hawaiian Islands
- Tiny house rentals Hawaiian Islands
- Rentals with a sauna Hawaiian Islands
- Rentals with a beach view Hawaiian Islands
- Guest house rentals Hawaiian Islands
- Tent rentals Hawaiian Islands
- Farm stay rentals Hawaiian Islands
- Flat rentals Hawaiian Islands
- Rentals with lake access Hawaiian Islands
- Rentals with breakfast Hawaiian Islands
- Waterfront rentals Hawaiian Islands
- Private suite 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
- Loft rentals Hawaiian Islands
- Pet-friendly rentals Hawaiian Islands
- Rentals with an accessible-height toilet Hawaiian Islands
- Rentals with a kayak Hawaiian Islands





