
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!
Stayed at Mollies for 11 days with our two adult kids and daughter in law! Pictures and words cannot describe how beautiful and perfect Mollie’s home was! Everything was absolutely pristine! There is not one detail that wasn’t thought of when making this Airbnb! Not to mention the pool and spa are absolute heaven! Mollie herself went above and beyond to help us plan daily activities and give us secret beach locations and restaurants to try! All were amazing! I definitely recommend this home to everyone. We can’t wait to come back!

Big House with ocean view and private pool in Kona
Chelsea was out of town yet was immediately responsive to messages dealing with a couple of minor glitches; it helped that the owner lives nearby. Place overall was great. Lack of air conditioning (it was not hot, but the upstairs did warm up in the April afternoons) was offset by the private pool, a better way to cool off than by refrigerating the house. Nice layout for two couples, one upstairs with the larger bedroom and large en suite bath, the other downstairs with two smaller bedrooms and a bath, so we each had good private space. Only drawback was the downstairs rooms seemed a bit enclosed, although all had windows. Nice large lanai and the landscaping around the pool made it feel especially private. Be sure to investigate the pantry and shelves before shopping...the place was very well supplied when we arrived. We would definitely stay again if we're in Kona!

Private Pool - 180° Ocean View - Minutes to Beach
This was the best first Airbnb experience. We were celebrating our 10-year anniversary with our 3 young kids. This home was just beautiful. The photos do not do enough justice. The home was super spacious and TV in both rooms. Our 5yr old enjoyed the jacuzzi because it was shallow and warm. The pool was huge with a diving board. It was nice having the outdoor kitchen and grill. We were able to prepare our food while also watching the kids swim. We enjoyed her papayas, avocados, and mango. Ms. Sandra shared with us her organic eggs from her chickens, Kale, beets, basil, and lettuce from her garden. Every morning when I woke up, I couldn't wait to open the curtains and windows to see the view and hear the birds. I could go on and on about this place. Thank you Ms. Sandra. It was such a pleasure meeting you and spending time in you beautiful home🙏

Tiny House Hawaii
Marylin, Steve and Craig were wonderful hosts. As soon as we came onto the property we felt right at home and part of the family. We were greeted with fresh fruit from the beautiful garden and fresh baked banana bread. You are surrounded by a lush tropical garden and many floral bouquets are throughout the tiny home. Craig made us the best coffee and provided us with some local Ube baked goods. Our favorite part of the property was going to sleep with the sound of croaking frogs. This place is truly a little slice of heaven! Hopefully we can come again! ❤️

Walua Oasis 2/2 Private Pool
Our group absolutely loved our stay. The host was extremely responsive and the pictures don't even do the place justice. We loved the view and relaxing by the pool until it was time to hit the beach. The location is ideal; it is not too far from Kona (8 minute drive) but you feel like you're in a jungle oasis.

Big Family Home, Pool, Views, Yard, Lanai, Clean!
This place was exactly what we were looking for, a private place with a pool. It was a great base for our vacation where we could come back after a day of being out and about. We could also just BBQ and relax in the pool. They had beach gear for use, which was very convenient. overall we had a good time.

Ocean, Sunset, Mountain & Celestial Views
This place was fantastic. The view is amazing- ocean, stars, mountains, it literally has it all. It’s super family friendly, tons of stuff to help you if you are traveling with an infant, toys, yard, safe space, play pen— everything you could need. It’s in a great spot with beautiful beaches ten minutes away. The hosts are so incredible. We grilled out on the deck watching the stars, picked fruit in the yard, enjoyed Kona coffee. If you stay anywhere else on big island you are missing out. This is a must stay and an incredible experience. We will return ❤️

Halia Hale
We loved every minute at Nicki's place. She met us at the door for a really helpful welcome tour and was always very quick to respond to inquiries about things to do in Kona and beyond. The beds were super comfy and the house was airy with tons of big windows and doors with screens, so it was a lovely place to relax. The pool is way bigger than we expected - perfect for laps after sitting in the sauna. The water temp was pretty cold, though, as it's not heated and it had been cloudy for a while, so the kids didn't really use the pool. But they kept busy by picking fruit from the many trees surrounding the house. Oh and the view, of course - amazing! Very close to the house is Mountain Thunder Coffee, which offers free tours of their facility so you can see why Kona coffee is so unique - a big hit for kids and adults alike. We can't recommend Nicki's place more highly - would have loved to stay longer!
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
We thoroughly enjoyed our stay. The view was outstanding and great to see surfers every morning and afternoon. The condo itself was very comfortable and would stay here again.

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!
Staying at Ineke’s place was a fantastic experience! The location was perfect—close to everything we needed—and the home was equipped with all the amenities to make our stay comfortable. The bed was large and very comfortable, and all the appliances worked flawlessly. We especially appreciated the thoughtful local recommendations, which made exploring Hawaii so much easier and more enjoyable. Overall, it was a wonderful stay, and I would definitely book this place again!

Kona Makai 3-203
The place was pretty clean and had all we needed for our stay. The A/C works great!
Quick stats about vacation rentals with a pool in Kailua-Kona
Total rentals
1.9K properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
68K reviews
Family-friendly rentals
930 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
1K properties have a dedicated workspace
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