
Vacation rentals with a pool in Kailua-Kona
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Top-rated rentals with a pool in Kailua-Kona
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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, you are a short walk to downtown. The condo looks directly out to the Pacific Ocean and is on the ground floor (no long stairs to climb). FREE dedicated parking spot! Free parking is so IMPORTANT in KONA now! 65" SMART TV, AC, our SOFA folds to a 2nd bed.

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!

Cozy Couples Retreat- Guest Suite w/ Pool & Patio
Perched above Kona on a serene hillside, the Monkeypod Villa offers a peaceful escape on a private country estate. Nestled off the beaten path & away from tourist crowds, you're just a scenic 7-mile drive from downtown Kona and pristine beaches. Wake to the gentle chorus of birds and sip your morning coffee beneath the shade of a magnificent monkey pod tree. After a day of exploring the Big Island, take a refreshing dip in the pool & unwind as the sky transforms with a stunning Hawaiian sunset.

Stunning Serene Bali Retreat [Pool/AC/Ocean View]
Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai and Balinese architecture, hand-carved wood, and ample windows and skylights that showcase the beauty of the Big Island. The kitchen/living room connect to the owner's retreat via a covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a cooler temps than busy downtown while not being far from the action. Owner-hosted by locals!

Oceanfront Gem, Walk to Beach/Town, AC, Elevator
Right-on-the-ocean, newly renovated, spacious, upscale condo in a gated boutique complex. Unbelievable views from the lanai, living room and bedroom. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and shops in Kailua Village. New king bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Heated, ocean-front salt water pool with outdoor shower and community BBQ. Quiet; no noise from Ali'i Drive. Reserved parking spot. A/C. Elevator.

Updated condo with ocean views & air conditioning
Kick back and relax at this renovated condo with partial ocean views, an oceanfront saltwater pool, and lusciously landscaped grounds. This air-conditioned unit boasts a central location just 1.3 miles from the heart of downtown Kona. Conveniently located between downtown Kona and the world-famous Magic Sands beach, this is the perfect home base to explore everything Hawaii Island has to offer. Enjoy the shared BBQs and private sandy beach area as you soak up Kona's sensational sunsets.

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.

Keauhou Garden - Ocean view - Walk to Harbor
Stunning ocean views, walking distance to the harbor and shopping center. Keauhou Garden is a clean and cozy stay at the heart of Keauhou, one of the best neighborhoods to stay on Big Island. Peaceful and quiet place, yet just a short drive from Kona downtown. A perfect place to unwind and relax while admiring beautiful views of the ocean and the golf course. Keauhou Resort is nestled next to the Kona Country Club, a spectacular public golf course with breath-taking ocean views.

Plantation Hale
Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

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.

Blissful paradise with epic view- Hale Mahana
Serenity in Kona- with epic ocean views! Wake up with the ocean waves crashing below. Hang out on the lanai with some Kona coffee from the Green Flash cafe next door. You have a front row seat for whale watching during whale season. Or, hang out and enjoy the sunsets- at times with our local manta ray! We have a queen sofa bed, and AC. Close to town- an 18 minute walk. Quiet, very little road noise here. You can rent bikes too across the street.
Popular amenities for Kailua-Kona rentals with a pool
House rentals with a pool

Mollie’s Paradise Resort Home & Private Pool

Exceptional Oceanview Home - Pool & Stunning View

Kahaluu Bay Get-Away

Private Pool - 180° Ocean View - Minutes to Beach

Tropical Oasis Home with Pool and Steps to Beach

Tiny House Hawaii

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC

HAVEN: Poolside Sanctuary with Heavenly Views
Condo rentals with a pool

TOP FLOOR, OCEAN VIEW, INCREDIBLE LOCATION

The Olena at Keauhou Bay

Ocean Front Corner Condo in Paradise

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

Kalanikai Condos! 5 Min walk to Kona Pier!

Hawaii Retreat with Beautiful Ocean View and AC

Heart of Kona Studio near beach!

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

Ocean View Pool Home. Kona Tropical Oasis.

Just A Few Steps To The Beach

Centrally Located Downtown Kona Condo

Ocean view with central location tropical paradise

Brand NEW Oceanfront Retreat! Steps to Beach!

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

Updated Kona Condo • Central • <1 Mile to Ocean

*Oceanfront Penthouse in Kona with AC!*
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ911 | ﺩ.ﺇ973 | ﺩ.ﺇ881 | ﺩ.ﺇ852 | ﺩ.ﺇ793 | ﺩ.ﺇ801 | ﺩ.ﺇ775 | ﺩ.ﺇ709 | ﺩ.ﺇ731 | ﺩ.ﺇ812 | ﺩ.ﺇ771 | ﺩ.ﺇ867 |
| 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 vacation rentals with a pool in Kailua-Kona

Total vacation rentals
Explore 1,970 vacation rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 73,780 verified reviews to help you choose

Family-friendly vacation rentals
990 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
1,070 properties have a dedicated workspace

Wi-Fi availability
1,960 of Kailua-Kona vacation rentals include wi-fi 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
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