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Vacation 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.

Guest favorite
Home in Pāhoa
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.
Jan 6 – 13
$225 per night
Guest favorite
Cabin in Maui
★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✔
Aug 7 – 14
$633 per night
Guest favorite
Condo in Waianae
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.
Dec 10 – 17
$310 per night

Popular amenities for Hawaii rentals with a pool

House rentals with a pool

Guest favorite
Home in Kailua-Kona
Halia Hale
May 23 – 30
$450 per night
Guest favorite
Home in Kihei
Stunning ocean view, heated pool at home by Wailea
Aug 8 – 15
$473 per night
Guest favorite
Home in Kapaʻa
Sleeping Giant Cottage with Plunge Pool TNVC 1244
Jul 17 – 24
$317 per night
Guest favorite
Home in Kailua-Kona
Private Pool - 180° Ocean View - Minutes to Beach
Dec 14 – 21
$495 per night
Guest favorite
Home in Pepeekeo
Hamakua Coast Tropical Home
Sep 10 – 17
$357 per night
Guest favorite
Home in Pāhoa
Puna Rainforest Retreat Hotspring: Green Bamboo
Sep 14 – 21
$134 per night
Guest favorite
Home in Princeville
Victoria Loop w/Private Pool! A/C+Waterfall Views
Sep 7 – 14
$564 per night
Guest favorite
Home in Captain Cook
Milolii Whale House With Ocean Views and Pool!
Feb 3 – 10
$299 per night
Guest favorite
Home in Captain Cook
Tiny House Hawaii
Aug 29 – Sep 5
$154 per night
Guest favorite
Home in Kailua-Kona
Tropical Oasis Home with Pool and Steps to Beach
Aug 23 – 30
$408 per night
Guest favorite
Home in Kailua-Kona
Classic Kona 🤙🏻 \\ Epic Ocean View 🌊 \\ Pool 🏊
Aug 6 – 13
$388 per night
Guest favorite
Home in Waikoloa Village
1+ Acre private resort, 4 bed, 3 bath, cinema, spa
Feb 2 – 9
$689 per night

Condo rentals with a pool

Guest favorite
Condo in Honolulu
Modern Condo_Free On-Site Parking_Car 4 Rent
Dec 14 – 21
$189 per night
Guest favorite
Condo in Kapaʻa
Amazing Ocean View! Fall In Love with Kauai!!❤️
Nov 25 – Dec 2
$378 per night
Guest favorite
Condo in Waialua
True Jewel - Oahu North Shore
Apr 28 – May 5
$389 per night
Guest favorite
Condo in Princeville
Brand New Luxurious Condo on North Shore Kauai
Jun 4 – 11
$500 per night
Guest favorite
Condo in Kailua-Kona
Deluxe Oceanfront Studio Condo@The Kona Bali Kai
Jan 22 – 29
$296 per night
Guest favorite
Condo in Lihue
Oceanfront, Private Lanai, Steps to Beach
Dec 6 – 13
$449 per night
Guest favorite
Condo in Kihei
Romantic, Luxury Maui Getaway with Ocean View
Jan 14 – 21
$425 per night
Guest favorite
Condo in Princeville
~The Surfshack~ with breathtaking ocean views!!
Nov 3 – 10
$550 per night
Guest favorite
Condo in Kailua-Kona
Gorgeous Oceanfront Condo - AC & Free WIFI/Parking
Jan 7 – 14
$375 per night
Guest favorite
Condo in Princeville
Divine Oceanfront Condo, Spectacular Sunset Views!
Dec 13 – 20
$638 per night
Guest favorite
Condo in Honolulu
Waikiki Beachfront, Amazing Views, Amazing Pools
Dec 28 – Jan 4
$678 per night
Guest favorite
Condo in Lihue
OCEAN FRONT private parlor @Marriott beach club
May 30 – Jun 6
$391 per night

Home rentals with a private pool

Guest favorite
Home in Waimea
Sea Glass House at Kamilo with Private Pool and Spa
Sep 12 – 19
$895 per night
Condo in Kahuku
Turtle Bay Fazio First Tee 13
Jul 11 – 18
$398 per night
Condo in Honolulu
Waikiki Banyan Condo One Block to Waikiki Beach!
Nov 27 – Dec 4
$202 per night
Condo in Honolulu
Waikiki Banyan Condo, Diamond Head & Beach View
Jan 6 – 13
$259 per night
Condo in Kahuku
Turtle Bay Hale Lilly
May 7 – 14
$475 per night
Condo in Kahuku
Turtle Bay Hula House Budget Ta-038-906-1120-01
Mar 17 – 24
$315 per night
Condo in Kahuku
Turtle Bay Takanoha
May 22 – 29
$406 per night
Condo in Kahuku
Turtle Bay Sage
Aug 24 – 31
$529 per night

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