Vacation rentals with a pool in Island of Hawai'i

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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.

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.
Nov 14 – 21
$225 per night
4.93 out of 5 average rating, 358 reviews
Guest favorite
Condo in Kailua-Kona
Aloha Paradise! Remodeled with A/C & Ocean View!
Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!
Dec 17 – 22
$177 per night
4.93 out of 5 average rating, 154 reviews
Guest favorite
Condo in Kailua-Kona
Deluxe Penthouse Oceanfront Studio Condo w/ A/C.
Direct Ocean front Condo! Free Wifi (500 Mps download speed) and free off street parking! Totally remodeled with new furnishings, king size pedestal bed, new sofa, bar stools, freshly painted, new ceiling fans, lighting and new split system central A/C! The condo is fully stocked with all the comforts of home plus many items you have never even thought about. The condo has a full size washer, dryer, dishwasher, a full suite of kitchen appliances, beach towels, beach chairs and snorkel gear.
Feb 5 – 12
$358 per night
4.95 out of 5 average rating, 113 reviews

Popular amenities for Island of Hawai'i rentals with a pool

House rentals with a pool

Guest favorite
Home in Kailua-Kona
Halia Hale
Aug 17 – 24
$450 per night
4.96 out of 5 average rating, 160 reviews
Guest favorite
Home in Captain Cook
Milolii Whale House With Ocean Views and Pool!
Oct 22 – 29
$299 per night
4.96 out of 5 average rating, 146 reviews
Guest favorite
Home in Kailua-Kona
Private Pool - 180° Ocean View - Minutes to Beach
Nov 23 – 30
$455 per night
4.95 out of 5 average rating, 137 reviews
Guest favorite
Home in Pāhoa
Puna Rainforest Retreat Hotspring Rainbow Cottage
Jan 8 – 15
$123 per night
4.9 out of 5 average rating, 456 reviews
Superhost
Home in Pepeekeo
Hamakua Coast Tropical Home
Aug 29 – Sep 5
$388 per night
4.86 out of 5 average rating, 144 reviews
Guest favorite
Home in Kailua-Kona
Classic Kona 🤙🏻 \\ Epic Ocean View 🌊 \\ Pool 🏊
Apr 15 – 22
$229 per night
4.94 out of 5 average rating, 188 reviews
Guest favorite
Home in Captain Cook
Tiny House Hawaii
Dec 26 – Jan 2
$154 per night
4.97 out of 5 average rating, 159 reviews
Guest favorite
Home in Waikoloa Village
1+ Acre private resort, 4 bed, 3 bath, cinema, spa
Nov 5 – 12
$697 per night
4.93 out of 5 average rating, 184 reviews
Guest favorite
Home in Kailua-Kona
Tropical Oasis Home with Pool and Steps to Beach
Sep 9 – 16
$438 per night
4.89 out of 5 average rating, 113 reviews
Guest favorite
Home in Honomu
Honomu Place: Pool, Slide, Hot Tub, Netflix & Gym
Jan 6 – 13
$500 per night
4.88 out of 5 average rating, 121 reviews
Guest favorite
Home in Waikoloa Village
Big Family Home, Pool, Views, Yard, Lanai, Clean!
Sep 18 – 25
$499 per night
4.88 out of 5 average rating, 123 reviews
Superhost
Home in Kailua-Kona
Aloha E Komo Mai! Welcome to Miracle Hale!
Nov 6 – 13
$724 per night
4.83 out of 5 average rating, 154 reviews

Condo rentals with a pool

Guest favorite
Condo in Kailua-Kona
Deluxe Oceanfront Studio Condo@The Kona Bali Kai
Nov 15 – 22
$288 per night
4.96 out of 5 average rating, 120 reviews
Guest favorite
Condo in Pahala
'Âlani Punalu'u Black Sand Beach oceanview retreat
Jul 24 – 31
$166 per night
4.91 out of 5 average rating, 405 reviews
Guest favorite
Condo in Kailua-Kona
Right-on-Ocean; Renovated; Walk to Beach/Town, A/C
Oct 3 – 10
$325 per night
4.96 out of 5 average rating, 160 reviews
Guest favorite
Condo in Kailua-Kona
Ocean Front Kona Reef A35! It doesn't get better!
Jul 18 – 25
$375 per night
4.97 out of 5 average rating, 183 reviews
Guest favorite
Condo in Kailua-Kona
Blissful paradise with epic view- Hale Mahana
Nov 4 – 11
$259 per night
4.92 out of 5 average rating, 141 reviews
Guest favorite
Condo in Kailua-Kona
Seaside Chic OceanFront @ Kona's Sea Village
Jan 11 – 18
$336 per night
4.96 out of 5 average rating, 125 reviews
Guest favorite
Condo in Kailua-Kona
Tropical Oceanfront Beauty - Magic Sands Beach
Jan 10 – 17
$345 per night
4.91 out of 5 average rating, 182 reviews
Superhost
Condo in Pahala
Hala Kahiki Punaluu | Ocean View | Cozy Lanai
Oct 19 – 26
$131 per night
4.9 out of 5 average rating, 189 reviews
Superhost
Condo in Kailua-Kona
SALTY LIVIN’ at Kona Makai (Tax Included)
Mar 26 – Apr 2
$190 per night
4.9 out of 5 average rating, 137 reviews
Superhost
Condo in Kailua-Kona
☀ Live on the Ocean along Famous Ali'i Drive + ☀
Jan 7 – 14
$287 per night
4.87 out of 5 average rating, 361 reviews
Guest favorite
Condo in Kailua-Kona
Oceanfront living - Floor to Ceiling wall of glass
Sep 12 – 19
$354 per night
4.92 out of 5 average rating, 103 reviews
Guest favorite
Condo in Kailua-Kona
Sunset Oasis in Paradise
Jul 23 – 30
$160 per night
4.87 out of 5 average rating, 212 reviews

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