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

Oceanfront/Hawaiian Charm W/Modern Amenities
Welcome to Hale Kani Moana (House of Ocean Sounds❤️)…the best location, city center on world famous Ali’i Drive. Cozy Hawaiian Charm w/ modern amenities. At your doorstep are the best restaurants, nightlife, and shopping. Stunning oceanfront unit w/sunset views (Fall/Winter). Listen to the ocean waves gently crash as you fall asleep. Fully stocked kitchenette, bathroom/shower, and all the beach equipment you’ll need. FREE Parking+FAST Wifi :-) Note: 3rd (Top Floor) stairs only, no elevators

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 :)

Spectacular View, Direct Oceanfront Kona,Top Floor
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGE Our lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the never ending sound of waves throughout the condo. Enjoy a closet full of essentials for visiting gorgeous beaches on the island. Downtown Kailua-Kona is a short mile walk from the condo, or relax at the oceanfront pool and hot tub!

Peaceful Paradise
Experience ALOHA in this spacious, ocean view gem providing a place of delight and relaxation. 2 miles to downtown Kona. Comfortable, clean, sun-kissed and welcoming - perfect for unwinding after a day of island sight-seeing. The charming, stylish space has a private entrance and is located on the ground floor of a large two-story home. You will experience all the comforts of home including an ohana kitchen, living area, bbq, and lovely, large outdoor lanai. Our goal is to give 5 star stays

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!

Longboard Studio at Kona Magic Sands Beach
Welcome to LongBoard Studio – Kona’s premier direct oceanfront escape at Magic Sands Beach! This stylish, film-featured studio offers stunning ocean views, a brand-new lanai with teak furniture, and full-width NanaWall doors for seamless indoor-outdoor living. Enjoy a gourmet kitchen, AC, queen bed, in-unit laundry, and the sound of waves at your doorstep. Perfect for relaxing, writing, or watching dolphins & whales from your lanai. Steps to the beach, serenity, and aloha! TA-005-037-8752-01

Ocean Views~by Honl's Beach~Heart of Kona~AC
ENJOY OCEAN VIEWS from a newly renovated Stylish condo in one of Kona's most desirable locations. Condo is an apx 6 to 8 min walk to a variety of Ocean Side Restaurants, entertainment and a quick walk to Honl's Beach. No rental car is needed as you are a short walk into town. The condo looks directly out to the Pacific Ocean and is on the ground floor so (no long stairs to climb). Free dedicated parking spot, which is so IMPORTANT in KONA now! 65" SMART TV, AC, the SOFA folds to a 2nd bed.

Suite Magic Sands Beach
Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

Downtown Kona Plaza Condo w/AC
Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

Poolside Studio🤙🏻Ocean View / AC / King🛌10min➡️Beach
A gorgeous remodeled studio featuring an ocean view lanai with a pool right outside. The lanai has a huge umbrella and bbq, and is a fully enclosed dining area with a self-closing gate to keep your kids safely away from the pool. The interior is all freshly renovated in 2020 with stylish and comfortable furniture. Covered parking is steps from the entry and plenty of quality beach gear is available for you to use anytime. Ice-cold A/C and Apple TV make relaxing inside just as nice.

1-Bedroom Suite with Private Pool and Garden Lanai
🌬AC included in price! ☀️We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

On-the-Ocean; Stunning Corner Unit, Spacious, A/C!
Right-on-the-ocean, newly renovated, upscale and spacious condo in a gated boutique complex. Unbelievable views from the lanai and living room. Top floor corner unit with windows everywhere so you feel like you are living outside. King bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Ocean-front pool with community BBQ. Quiet; set back from Ali'i Drive. Close to everything--just one mile from downtown Kona. Reserved parking spot. AC.
Popular amenities for Kailua-Kona rentals with a pool
House rentals with a pool

Mollie’s Paradise Resort Home - No Cleaning Fee!

Exceptional Oceanview Home - Pool & Stunning View

Private Pool - 180° Ocean View - Minutes to Beach

Tropical Oasis Home with Pool and Steps to Beach

Tiny House Hawaii

HAVEN: Poolside Sanctuary with Heavenly Views

Panoramic Ocean Views With Private Saltwater Pool

Big Family Home, Pool, Views, Yard, Lanai, Clean!
Apartment rentals with a pool

Oceanfront Condo/Hawaiian Style. 1Bd, w/AC & Wifi

Keauhou Garden - Ocean view - Walk to Harbor

2 Bedroom Penthouse Condo With Ocean View And Pool

Hawai'i paradise at Kona Isle

O/F View, on ocean 1 Bdrm, Casa De Emdeko Ironman

Honua Studio *Ocean Views on the Golf Course!

Plantation Hale

Studio condo, King bed, pool view on Alii Drive
Other holiday rentals with a pool

1 BR condo steps from Kona's premier surf break

Centrally Located Downtown Kona Condo

Brand NEW Oceanfront Retreat! Steps to Beach!

Stunning Oceanfront Beach Condo!

NEW! ADORABLEbungalow in Kona

1BR Kona Condo w/ Chef’s Kitchen & Tropical Lanai

Brand new Luxury Oceanfront Living in Kona with AC

Oceanfront Chic • Just Renovated
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £186 | £199 | £180 | £174 | £162 | £163 | £169 | £165 | £156 | £175 | £165 | £178 |
| Avg. temp | 6°C | 6°C | 6°C | 7°C | 9°C | 10°C | 9°C | 9°C | 9°C | 9°C | 7°C | 6°C |
Quick stats about holiday rentals with a pool in Kailua-Kona

Total holiday rentals
Explore 1,940 holiday rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 73,110 verified reviews to help you choose

Family-friendly holiday rentals
970 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
1,050 properties have a dedicated workspace

Wifi availability
1,920 of Kailua-Kona holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kailua-Kona rentals

4.8 Average rating
Kailua-Kona stays are highly rated by guests – averaging 4.8 out of 5!
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- Hapuna Beach
- Pahoa Beach
- Kaunaoa Beach
- Mauna Kea Golf Course
- Kohanaiki Private Club Community
- Ke‘EI Beach
- Waikōloa Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- Waikoloa Beach Golf Course
- 49 Black Sand Beach
- Kona Dog Beach
- Kuki’o Golf & Beach Club
- Hapuna Golf Course
- Makalawena Beach
- Kona Country Club
- Nanea Golf Club
- Kealakekua Bay State Historical Park
- Mauumae Beach
- ʻAlula Beach
- Honokohau Beach
- Pololū Beach
- Mahaiʻula Beach
- Wawaloli Beach
- Things to do Kailua-Kona
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