
Holiday rentals with a pool in Island of Hawai'i
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Island of Hawai'i
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Ocean, Sunset, Mountain & Celestial Views
🌴 Guest Favorite - Top 10% on the Big Island Enjoy stunning ocean, mountain, sunset, and starry views from nearly every room in this cozy, family-friendly three-bedroom, two-bathroom Waikoloa Village, Hawaii home. The house includes everything you'll need on your paradise escape including a fully equipped kitchen, beach gear such as boogie boards, snorkels, coolers, umbrellas, towels and Wi-Fi. We also provide bath towels, bed linens, soaps/shampoos, coffee, children's toys, and a BBQ grill.
LocationFamilyHiking

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
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Seahorse Luxury Suite at Seaspray Ocean View
A private oasis across from the desirable Kahaluʻu Beach Park. This two bedroom luxury suite is bright & airy with a private lanai & your own KOI pond. A private guest only pool deck includes a barbecue and dining area for outside entertainment. The living room is a great place to relax with ocean views and the sounds of ocean waves. The chef of the family will appreciate a fully stocked modern kitchen. The whole group will enjoy everything Kona has to offer from this centrally located Oasis.
ValueFamilyOutdoor spaces

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.
ValueFamilyPool

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.
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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.
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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.
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Huge Kona Home • Ocean View • Pool • 4 bdrms • AC
Bringing the whole crew—or two families? This breezy 4BR, 3BA Kona home is built for fun and flexibility. Two stories mean plenty of space to gather—or sneak off for quiet time. With two kitchens, two living rooms, A/C, smart TVs, and indoor laundry, everyone gets room to relax. Take in an almost 180° ocean view of Kona bay, lounge on breezy lanais, fire up the BBQ, or float in the pool. Pick fresh mangoes and starfruit on-site. Just 5 mins to Kona town—your perfect island escape awaits.
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Newer Luxury Townhouse - Exceptional Value
Hali'i Kai is the nicest ocean front condo resort property in Waikoloa Beach and arguably along the entire Kohala Coast. The grounds & amenities are very nice and appealing to the most discerning of guests. - Ocean Club with its lagoon style pool - Sand bottom hot tub - Ocean front fitness center - Resort bar & restaurant - Tennis and basketball - Beach toys, umbrellas, chairs - Amazing beaches - 2 Pro golf courses - Outdoor shopping - More than 15 restaurants - Great snorkeling
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Pineapple Palace~Stunning Ocean Views~Private Pool
The Pineapple Palace is located on one acre in the quiet rural area of Milolii. The home is near City of Refuge, Punalu'u Bakery, South Point, Pu'uhonua O' Honaunau, The Coffee Belt, and is on the way to Volcanoes National Park. You’ll love my place because of the comfy beds, the high ceilings, the views, the Private Pool, the well stocked kitchen. My place is good for families (with kids) and big groups. NEW FIBER OPTIC HIGH SPEED INTERNET 600 MBPS INSTALLED APRIL 2024.
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OCEANFRONt 3+2.5 FREE AC BeachGear
OCEANFRONT Kanaloa 3Br 2+1/2 Ba AC SPACIOUS 2000 sq ft. FREE Parking. FREE Resort Fees. FREE AC. Enjoy Meals Out on your Oceanfront Lanai. King Beds. Twins avail. Walk to Keauhou Harbor (Snorkel Tours, Manta Ray Boats), Secret Cove (Hee'eia), Movies, Market, Restaurants 5 min drive to Kahaluu 3 Pools, Hot Tubs, BBQs, Clubhouse, Oceanfront walkway, 16 Acres of tropical grounds. 15 Stairs 2 night min $298 cleaning & 17.96% Hawaii tax is shown on your Airbnb quote.
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Halia Hale
Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.
LocationFamilyBeach
Popular amenities for Island of Hawai'i rentals with a pool
House rentals with a pool

Hamakua Coast Tropical Home
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Gorgeous Gated Retreat w Pool Deck Firepit, 1 acre
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HAVEN: Poolside Sanctuary with Heavenly Views
ValueLocationWi-Fi

Fully Equipped Lush Kona Home • AC • Pool • Lanai
LocationFamilyLaundry

Tropical Oasis Home with Pool and Walk to Beach
FamilyLocationNearby

Milolii Whale House With Ocean Views and Pool!
ValueFamilyCheckout

Beautiful home with pool, on Kaloli Point
FamilyValueTV

Ocean & Sunset Views + Island Aloha
ValueLocationNearby
Condo rentals with a pool

Ocean View 2BR Condo in Kailua-Kona
FamilyValueAir conditioning

True Oceanfront, Top-Floor, Downtown, A/C, Parking
FamilyValueAccuracy

Updated condo with ocean views & air conditioning
LocationFamilyAir conditioning

Hali‘i Kai Ocean View | 3BR/3BA | Sleeps 8
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Kona Landing | Ocean Views, BBQ, Pool, Beach Gear
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Ali'i Dr w/ Ocean Sunsets next to Farmer's Market
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Beachfront Condo in Kailua
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2 Bedroom Penthouse Condo With Ocean View And Pool
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Other holiday rentals with a pool

High-End Ocean Sanctuary with Upgraded Interiors
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Villa Paraiso Hawaii Huge Pool & Hot Tub. Up to 12
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Bright, Spacious, 3 bedroom 3 bathroom Townhome
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Hawaii Big Island Villa | Waikoloa Beach Resort
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Spacious Fairways 2BD townhome. Pool/Beach Club!
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Luxurious 3 bedroom at The Fairways at Mauna Lani
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Downtown Kona Loft•Ocean View•Walk to Beach/Dining
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Honua Studio *Ocean Views on the Golf Course!
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- Hapuna Beach
- Waikōloa Beach
- Mauna Kea
- Kohanaiki Private Club Community
- Waikoloa Beach
- Mauna Lani Beach Club
- Carlsmith Beach Park
- Honoli'i Beach Park
- Kilauea
- The Umauma Experience
- Sea Village
- Spencer Beach Park
- Manini'owali Beach
- Maku'u Farmer's Market
- Makalawena
- Puʻuhonua o Hōnaunau National Historical Park
- Magic Sands Beach Park
- Lava Tree State Monument
- Waialea Beach
- Kaloko-Honokohau Nat'l Hist Park
- Papakōlea Beach
- Onekahakaha Beach Park
- Pana'ewa Rainforest Zoo and Gardens
- Volcano House
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