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

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.

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, and ample windows and 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 cooler temps than busy downtown while not being far from the action. Solar/Tesla batteries keep power on!

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.

★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✔

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

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.

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

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.

Oceanfront Estate Retreat 2 - Solar w/ Horses
Experience unmatched luxury in a private, hi-end artistic apartment on 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 this spacious apartment featuring living, dining, desk, garden, sleeping, kitchen, bathroom with walk-in rainfall shower, bidet, and a luxurious furnishing. This property offers privacy, elegance, and stunning surroundings for singles, couples, or honeymooners.

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 Hawaii rentals with a pool
House rentals with a pool

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~The Surfshack~ with breathtaking ocean views!!

Longboard Studio at Kona Magic Sands Beach

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Jewel of the Pacific- Oceanfront Paradise

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Little Rainbow Kauai | Beachfront, AC, Ocean View

Spectacular Oceanfront Condo, A/C + Sunset Views!
Other holiday rentals with a pool

Cliff House w/ Ocean View Haiku, Maui Road to Hana

Hale Mar Oceanfront w/ Pool & Hot Tub

Spacious Fairways 2BD townhome. Pool/Beach Club!

Spectacular views, prime location Kapalua, Maui.

Kona Mansion Infinity Pool & Ocean Views (Hosted)

Brand NEW Oceanfront Retreat! Steps to Beach!

Luxury Ohana, 60ft Salt Pool,

Ohana With Private Pool & Jacuzzi
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