
Vacation rentals with a pool in Kailua-Kona
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Top-rated rentals with a pool in Kailua-Kona
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Popular amenities for Kailua-Kona rentals with a pool
House rentals with a pool

Mollie’s Paradise Resort Home - No Cleaning Fee!
Mollie's place was paradise!! Our family had such a wonderful stay there during our spring break for 8 nights. The home was super clean with all the amenities we needed. We enjoyed the private backyard with pool and hot tub every day. The beds were very comfy. The location was great as we ventured out every day and explored this beautiful island. When I did have questions, Mollie responded right away. The check in and check out process was very easy. Would definitely come back! Thanks Mollie!!

Beautifully Furnished 4 Bdrm Home At KaMilo w/Pool
The house was beautiful inside and out. My son loved the pool, which was the perfect temperature. The kitchen was well stocked and the house provided plenty of space for everyone.

Big House with ocean view and private pool in Kona
This house indeed has a magic lanai, with amazing sunset views and a beautifully private feeling. The lanai had a breeze if you were hot, and the pool was nestled calmly in trees and was a wonderful mid-afternoon reprieve, and great for the kids. The home itself is smartly designed to cool off quickly at night. Large space with easy flow. Chelsea and Rudi are very helpful When the washing machine broke (such is the randomness of life) it was easily arranged for us to be able to do the laundry next door. Loved the neighbourhood. Away from the busy Ali'i drive, but close enough to walk down to enjoy, or take a short drive. Private and quiet, this was a great home in which to unwind.

Private Pool - 180° Ocean View - Minutes to Beach
Sandra's place brings healing. It is beautiful, quiet, and serene. The views are lovely of ocean below, and the wind blows quietly through bows of citrus, avocado, and palms. There are likely multiple Walden Ponds on the Big Island of Hawaii, but this is one of them. Tranquility reins at this property.

Walua Oasis 2/2 Private Pool
Beautiful place! Great location. All the amenities you could need inside: shampoo/conditioner, laundry detergent, silverware/plates. Also all you could need for the beach including beach towels, umbrella, chairs, and a cooler. Perfect for a long stay. No AC but it cools down at night and we didn't mind. Would definitely recommend and stay again!

Big Family Home, Pool, Views, Yard, Lanai, Clean!
We went for a family vacation and fit everyone’s needs. Great for kids,grandparents and everyone in between. It was a wonderful place to be when we weren’t adventuring on island. Such a spectacular backyard to hangout in, patio for meals and kitchen for cooking. Everyone had their space! Andy and Bryn were quick with any questions we had. We look forward to booking again!

Halia Hale
We have never felt as at home is such a short period of time as we did at Nicki's beautiful place. Nicki herself is welcoming, friendly, and informative and the house is outstanding. The views, the cleanliness, and having everything you need at hand is simply top notch. it is very peaceful and secure but still close enough to everything. Highly recommended and would absolutely stay again (and again).

Beautiful Home With Private Pool on Kealakekua Bay
The Pagoda House is a destination in itself! We explored the island from there, but also spent time just hanging out in the garden and pool. GORGEOUS! It was well appointed for our extended family gathering.
Condo rentals with a pool

Kona by the Ocean
A beautiful clean condo. Great location. Loved the pool and hot tub and the ocean views from the grounds

Royal Kahili Condo with Lanai Ocean View
The accommodation was just like the picture. The clean and well-organized accommodation made our vacation start in a good mood. We were very comfortable during our stay, equipped with bathrooms and kitchen supplies, and we also used the rice cooker very well. It had two bathrooms, so it was good for our family to wash up after swimming in the sea. The bed was big and clean, but it was so fluffy for us that our backs hurt a little. It was also very convenient with 2 large boogie boards, a beach chair, parasol, flippers and other beach supplies. When we asked if we had any questions, the host answered us almost right away, so we were grateful. The pool and the Jacuzzi that starts late in the afternoon also made our vacation better. You can walk the Magic Sand and it takes only 10 minutes to get to Kona downtown. We are willing to stay again if you come to Kona again next time. I recommend this accommodation.

Stylish Condo with pool-10 minute walk to ocean
We had an amazing stay at David’s place in Kona! As a family of three, it was the perfect spot—comfortable, clean, and matched the description exactly. In fact, it exceeded our expectations in every way. The place actually looked even better than the photos, which is rare! One especially thoughtful touch: the AC was left on for us before arrival, which made walking into a cool, welcoming space after a long journey absolutely perfect. We've stayed at the Hilton Waikoloa before, but David’s place was far better—more private, more spacious, and much more relaxing. David was a fantastic host—super responsive and proactive in sharing local recommendations, which made our trip even more enjoyable. From nearby beaches to local eats, his tips were spot on. Highly recommend for anyone visiting the Big Island—especially families looking for a more personal and authentic experience!

2 Bedroom Penthouse Condo With Ocean View And Pool
Great condo away from tourist area but not far from restaurants and grocery stores. I like being in small building instead of big resort. Well stocked kitchen and furnishings up to date. Clean and quiet. Real hot tub with jets was nice after being out on excursions all day! Kristina was very responsive and helpful. The coffee grinder broke and she had on sent to me within an hour! I would definitely stay here again if I return to the big island again!

Oceanfront complex at Casa de Emdeko unit #102
Fantastic stay here! Great place and location, close to so much in Kona but still peaceful and relaxed. Rony was exceptional host: proactive, friendly, and flexible.

Beach Paradise
What a great find!!! Marco’s condo is everything as advertised & more! Beautiful view, quiet, clean, great new appliances. Location is easily walkable to all of Ali’i Drive. We ate breakfast on the lanai every morning, watching the paddlers, parasailers, and surfers. Complex has a fantastic pool & hot tub that are immaculately maintained. We miss it already!

Oceanfront 2 bed, 2 bath, kitchen with full AC!
This place was neat and clean. The kitchen was stocked with many of the things we needed. The host was very helpful and responsive. We really loved sitting on the lanai having our morning coffee as the sun came up. This place is on the west side of the island so we were able to catch a couple of beautiful sunsets as well. There were a lot of places to see and do in the town nearby. It is within walking distance but there is no sidewalk so at times it felt safer to drive there. We stayed here for 3 nights and wished we could have stayed longer. We recommend this place to anyone looking for a quiet place to enjoy Hawaii.

On-the-Ocean; Stunning Corner Unit, Spacious, A/C!
If you are looking for a place in Kailua-Kona, this is the place. I can get wordy, but there is no need. We loved this place and would stay there again without hesitation. Ineke was very helpful from initial inquiry to after check-in. You have to drive to the hotspot/market, but parking was not difficult, and merchants validated parking. Beaches and dining were nearby. Book it and enjoy!
Quick stats about vacation rentals with a pool in Kailua-Kona
Total rentals
1.6K properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
53K reviews
Family-friendly rentals
750 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
860 properties have a dedicated workspace
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- Waikōloa Beach
- Kealakekua Bay State Historical Park
- Kohanaiki Private Club Community
- Volcano Golf and Country Club
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- Two Step
- Kuki’o Golf & Beach Club
- Waikoloa Beach Golf Course
- Mauna Lani Golf
- Kona Country Club
- Pōhue Beach
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- Nanea Golf Club
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- Wawaloli Beach
- Makolea Beach
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- Mahaiʻula Beach
- Kealia Beach
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- Makalawena Beach
- Kukio Beach
- Mauna Kea Golf Course
- Hapuna Golf Course
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