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

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!

Kahaluu Bay Get-Away
Kahalulu Bay Get-Away is your perfect choice for an authentic, comfortable Hawaiian stay. Perched gently above Kahalulu Bay, you'll enjoy tropical tradewinds, Kona sunsets, the sounds of the surf and the songs of nature. The setting is totally private with ocean views, rock walls, large trees, lush greenery, an archeological site from the 12th century and a pool that is all-day worthy. Come. Relax. Enjoy. You’re in for a treat. Family built, enjoyed for decades and now shared with you...Aloha :)

Downtown Kona! Ocean View<1/2mi to Beach!
Say ‘Aloha’ to the good life when you book one of the best located condos in downtown Kailua-Kona! Located in the heart of downtown, this modern loft style home is just a 5-10 minute walk to the beach, the famous Alii Drive, restaurants, and on-the-water fun. Equipped with a private lanai and community amenities, you’ll have everything you need to enjoy Kona to it's fullest. Walk to the best downtown Kona Beach for a fun family-friendly day of sun, white sand, turquoise waters, and snorkeling!

☀ Live on the Ocean along Famous Ali'i Drive + ☀
Kona Bali Kai - Direct Ocean Front! Watch Whales, Turtles, Surfers, Dolphins, Beautiful Sunsets & morning coffee from your private balcony. Large 2 bedroom, 2 bathroom with washer and dryer inside. Wake up to sparkeling ocean views & sounds of surf from your bedroom & living room. Enjoy pool, hot tub, guest services, & world renown "Da Poke Shack" right downstairs! One of a kind experience! Free covered parking, all taxes & fees included in price! 2nd floor, Easy access, no hassle check in!

Puna Rainforest Retreat Hotspring: Purple Passion
The Purple Passionfruit Cottage has small kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed and an attached lanai with a ocean view. The other bedroom doubles as a living room with one twin bed. Enjoy the pool, rainforest trail, steam vents, volcanic hot spring tubs and private retreat setting surrounded by forest. Owners live on the 20 acre property to make sure everything is perfect for your stay. TA-008-365-8240-01

Welcome to your Hawaiian Getaway
Airport is 20 minutes away. Centrally located to Kailua Kona downtown which has many restaurants and grocery stores. 6 minute drive to White Sands Beach. Fantastic snorkel beach is 10 minutes away. Take a private night dive with the Manta Rays. Walk to Ali’i drive. Travel the island and come back to a relaxing space with a swimming pool. Drive to Hapuna beach and spend the day at a beautiful stretch of white sand along the coast of Kona. Also travel to the waterfalls a must see.

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.

In Town ALII ,Oceanview, 1 bdrm Ironman Kona Plaza
This is a lovely, well stocked, 1 bedroom, 1 bath condo. Tastefully decorated with a wonderful Hawaiiana Feel. Enjoy the over sized lanai, with comfortable furnishings, for reading, relaxing and dining. The evenings are peaceful with the waves crashing against the shore The sunsets are amazing, and the mornings are cool and quiet. Sleep well, in a large A/C king sized bedroom Beaches, restaurants, snorkeling, all within a quick walk. OVER IRONMAN THE RATE GOES UP AND IT IS A 9 NIGHTS.

Hale Honu - Oceanfront, AC, Pool, Hot Tub
Aloha from Koili Point! Our oceanfront 2 bdrm, 2 bath home has everything you need to relax. Great Wifi, pool, hot tub, AC, numerous appliances, and an open layout make it a retreat after a day of sightseeing. Free parking, washer/dryer and located just north of Hilo. Guests love our focus on eco-living and pesticide free orchard where you can pick your own fruit. We are powered 100% by solar. If this house is booked, check out our nearly identical house: airbnb.com/h/koilipoint-kohola

Unsurpassed sunset views!
One of the best locations in the Sea Village for privacy and gorgeous Sunset views! This well-appointed, remodeled 1 bedroom unit was hand-picked when brand new because it feels like you’re right over the ocean, fall asleep to the sound of the waves crashing outside, yet a close walk to the friendly town of Kona and so many wonderful restaurants! *Note: Taxes are included in the Daily Rate, saving you more than 18%! Hawaii Tax ID# TA-052-854-7840-01 GE-052-854-7840-01 STVR-19-360359

Lush Paradise—Luxury Eco-Getaway
Escape to our luxurious cedar home on Hawaii's main island. Surrounded by rainforest, waterfalls, and a stream, our sustainable retreat offers serenity just 25 mins from Hilo. With 4 beds, 2 baths, and an open-concept kitchen, our spacious home blends Hawaiian charm with modern amenities. Unwind on the travertine lanai, and explore fruit trees and trails. Perfectly located for beach adventures and vibrant towns. Experience tropical living at its finest. Book now!

Kehena Beach Loft
Rural Beautiful space across street from serene black sand beach. One hour from Volcano National Park. Take it easy at this unique and tranquil getaway. Kehena Beach loft is part of an one acre luxury estate. You will have your own private separate corner of property, you wont see another person. We are remote, tranquil, one with nature. A great place to unplug, listen and watch ocean waves come ashore. Near several local markets , black sand beach.
Popular amenities for Hawaii County rentals with a pool
House rentals with a pool

Beautiful home with pool, on Kaloli Point

Kai Malolo - Amazing Eco-friendly Oceanfront Home!

Tropical Oasis Home with Pool and Steps to Beach

Private Pool - 180° Ocean View - Minutes to Beach

Tiny House Hawaii

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

Milolii Whale House With Ocean Views and Pool!

Hamakua Coast Tropical Home
Apartment rentals with a pool

Longboard Studio at Kona Magic Sands Beach

Ocean Views~by Honl's Beach~Heart of Kona~AC

Condo with A/C, Pool, Spa & Golf Course Views

Aloha Paradise! Remodeled with A/C & Ocean View!

Updated Kona Condo • Central • <1 Mile to Ocean

Oceanview Kailua-Kona Condo with Lanai

Polynesian Koi Pond Gardens Condo in Hilo w pool

Honua Studio *Ocean Views on the Golf Course!
Other holiday rentals with a pool

Coastal Bliss: Modern Condo, Lanai, Hilton Pass

Mermaid's Lookout

2Bed Ocean View Condo in Keauhou

Cotton Candy Sky Kona Pacific Condo

Relax! Surfing & Racquet Club 5-201

NEW Ocean View Retreat-Pickleball/Golf/Tennis/Pool

Walua Oasis 2/2 Private Pool

#56 Colony One at Sea Mt. Punalu`u
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- Hapuna Beach
- Waikoloa Beach
- Waikōloa Beach
- Kohanaiki Private Club Community
- Kona Country Club
- Carlsmith Beach Park
- Mauna Lani Beach Club
- Lava Tree State Monument
- Honoli'i Beach Park
- Makalawena
- Manini'owali Beach
- Kilauea
- Mauna Kea
- Big Island Retreat
- Puʻuhonua o Hōnaunau National Historical Park
- Hapuna Beach State Recreation Area
- Spencer Beach Park
- Rainbow Falls
- Magic Sands Beach Park
- Kaloko-Honokohau Nat'l Hist Park
- Pololū Valley Lookout
- Waialea Beach
- Sea Village
- Punaluu Black Sand Beach
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