
Holiday rentals with a pool in Hawaii County
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Top-rated rentals with a pool in Hawaii County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Tiny House Hawaii
The Tiny House is ready to welcome you to a drop of heaven on the Big Island!🌴 Please be my guest for an exquisite experience in beauty, peace, and tranquility! The Tiny House is a separate guest quarters attached to the main house by only a breezeway. It has its own private entrance, covered lanai, and private yard. Everything you need for an amazing stay is included--- all cooking amenities, beach towels and chairs. The main house has a solar heated pool which is available for Tiny House guests, and a large deck with magnificant ocean and sunset views. Contact us at hitinyhouse@gmail.com for more information or to inquire about booking a stay.

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.

180 degree ocean view, private pool
Family friendly, NON SMOKING PROPERTY has a cottage with a 180 degree ocean view & beautiful pool. Enjoy incredible sunsets from the large deck, outdoor showers in the ginger garden & relaxing evenings in the hot tub. We welcome guests of all Races, religions, and sexual orientation! THERE IS NO LIFEGUARD ON DUTY NO DIVING IN THE POOL PLEASE THE SLIDE IS FEET FIRST ONLY! WE INVITE YOU TO PLEASE READ THROUGH THE FOLLOWING SECTION AS THERE IS OTHER PERTINENT INFORMATION FOR YOU AND YOUR FAMILY

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.

Puna Rainforest Retreat Hotspring: Green Bamboo
In a private retreat, this studio offers an idyllic escape with stunning ocean views. A full kitchen and bathroom with a queen-size bed for couples and additional small bed for a child or a small adult. This space is perfect for a romantic getaway or family vacation. Explore the one mile private rainforest trail, unwind in the pool, or experience the unique steam vent hot tubs. The owner resides on the 20-acre property to address any needs that may arise during your stay. TA-008-365-8240-01

Hamakua Coast Tropical Home
A beautiful tropical style custom home featuring private ocean views and a small gated pool. Our home was thoughtfully designed to maximize Hawaiian indoor/outdoor living and entertaining in a manicured park-like setting. A palm lined driveway leads you to a single level 3 bedroom, 2 1/2 bath residence located in the exclusive Pepeekeo Point subdivision, approx. 15 minutes from Hilo. Featuring a fiberglass pool with a bamboo pavilion& bbq for outdoor dining No parties or unregistered guests

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.

HAVEN: Poolside Sanctuary with Heavenly Views
HAVEN Where the changing colors of the heavens melt into the sea. This is a place where dreams are born and special moments unfold. Tranquility, privacy, and beauty await you. A masterclass of design in harmony with nature, this exquisite home beckons you; a salve for body and soul. Whether you are submerged in the saltwater pool or lounging inside one your deluxe bedroom suites, the views will enchant you, providing an ever-changing patina of color & light. Tax ID # TA-110-823-1680-01

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.

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.
Popular amenities for Hawaii County rentals with a pool
House rentals with a pool

Gorgeous Gated Retreat w Pool Deck Firepit, 1 acre

Mollie’s Paradise Resort Home & Private Pool

Beautiful home with pool, on Kaloli Point

Tropical Oasis Home with Pool and Walk to Beach

Pool, 6 mins to Beach, Ocean View, H7

Tranquil Hawaiian Pineapple Poolhouse with A/C

Big Family Home, Pool, Views, Yard, Lanai, Clean!

Hale Honu - Oceanfront, AC, Pool, Hot Tub
Apartment rentals with a pool

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

Beachfront Condo in Kailua

Inna's Downtown-Walk to Beach and to Supermarket!

2 Bedroom Penthouse Condo With Ocean View And Pool

Oceanview Kailua-Kona Condo with Lanai

☀ Live on the Ocean along Famous Ali'i Drive + ☀

Honua Studio *Ocean Views on the Golf Course!

Newer Luxury Townhouse - Exceptional Value
Other holiday rentals with a pool

Hale Mar Oceanfront w/ Pool & Hot Tub

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

Seahorse Luxury Suite at Seaspray Ocean View

Oceanfront gated estate w/heated saltwater pool.

Ohana With Private Pool & Jacuzzi

Villa Paraiso Hawaii Huge Pool & Hot Tub. Up to 12

Luxurious 3 bedroom at The Fairways at Mauna Lani

Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Views
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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
- Sea Village
- Manini'owali Beach
- Maku'u Farmer's Market
- Spencer Beach Park
- Magic Sands Beach Park
- Makalawena
- Puʻuhonua o Hōnaunau National Historical Park
- Waialea Beach
- Lava Tree State Monument
- Kaloko-Honokohau Nat'l Hist Park
- Papakōlea Beach
- Onekahakaha Beach Park
- Pana'ewa Rainforest Zoo and Gardens
- Volcano House
- Richardson Ocean Park
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