
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!
Mollies home was amazing. The open concept layout, from the kitchen to the pool, was a dream. Mollie was super communicative and genuinely wanted us to enjoy our vacation. I can’t recommend this place more… I think it’s my favorite Airbnb experience of all time.

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.

Spacious house w/ pool, fruit trees, on 1.5 acres
This house was the perfect property for our extended family of 9 to enjoy Kona and the surrounding areas! The location is great with a short, easy drive to both the airport and downtown and the property/yard is lovely. We found the home to be very comfortable and well stocked. The kids loved having the a little pool to themselves after a day at the beach and it was so nice that it was a bit cooler up on the hill in the evenings. The only thing I’d note is that there are several VERY vocal roosters in the vicinity. (This would be hard to avoid anywhere in Hawaii though I imagine!) If you are hoping to sleep in or are sensitive to noises, bring ear plugs or put on some white noise. We all adjusted to it quickly :) Thanks so much for hosting us Kim!

Big Family Home, Pool, Views, Yard, Lanai, Clean!
We were a family of 4 travelling for several months from Australia - this was one of our favourite Airbnb’s of the trip. The back garden was absolutely beautiful and super relaxing. We saw all types of birds while reading in the backyard. Having seen the hideous Kona we were so happy we booked away from the grime and noise and ended up in this lovely comfortable home - very near to plenty of stores and very well equipped for all our in house cooking. We would happily have stayed longer had we not pre-booked other plans. Thank you - would highly recommend!

Tropical paradise, heated pool, ocean views, AC
I recently stayed at Justin’s Airbnb in Kona, and it was an amazing experience. From the moment we arrived, Justin was incredibly welcoming, offering great recommendations for local activities and making sure we had everything we needed. The house itself was spacious, clean, and beautifully decorated, creating a perfect island retreat. One of the highlights was the pool – it was pristine and provided the perfect spot to relax after a day of exploring the island. The outdoor area was fantastic, with plenty of seating, and we enjoyed several evenings watching the sunset from the lanai. The location in Kona was ideal, with easy access to beaches, dining, and shopping, yet the house felt like a private oasis. We felt truly at home during our stay and couldn’t have asked for a better place to unwind. I highly recommend Justin’s place for anyone looking to experience the best of Kona in comfort and style!

Halia Hale
We had a wonderful stay at Nicki’s Airbnb in Kona! The location was perfect—close to everything we wanted to see and do, yet peaceful enough to truly relax. The views were absolutely stunning, making it a great spot to unwind in the mornings and evenings. The home was spotless upon arrival, and it was clear that cleanliness is a priority. Nicki was a very responsive and helpful host, making check-in and communication smooth and easy. Overall, it was a fantastic stay, and we would definitely book again!
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
This condo came highly recommended by friends and it did not disappoint! The condo is well equipped and very clean. It is completely updated and has a spa like master bathroom. The beds were so comfortable!! The unit has central air-conditioning which was greatly appreciated! Excellent location…an easy walk to a convenience store and several markets. Great snorkelling is also available close by. Brenda is lovely! She provided helpful information to ensure a comfortable stay and a great island experience. The private balcony with an ocean view was amazing. We were able to walk across the street to see the sunset every night! The ocean waves also allowed us to watch surfers throughout the day. We would stay at this specific condo again when we return to the island!

Stylish Condo with pool-10 minute walk to ocean
This place is 10 min walk to the beach. It is also walkable to restaurants and stores. You get a car parking, snorkeling gear, chairs, boogie boards for the family to enjoy. All in all, great space so the family doesn’t have to go look around for parking

2 Bedroom Penthouse Condo With Ocean View And Pool
We had a great stay here. Absolutely beautiful view from the unit over the ocean with gorgeous sunsets. Easy, short drive to Kona for restaurants and other shopping needs. Well equipped kitchen and easy parking. Only minor issue was there were no shades to block the late afternoon sun in the unit. We'd happily stay here again.

Beach Paradise
We enjoyed our stay and wouldn't hesitate to rent again from Marco. The condo was well equipped for cooking and relaxing. There were only two of us so we couldn't comment on the sleeper sofa. The washer and dryer were convenient and worked well. Marco always responded quickly to our questions and concerns. The views out to the pool and shore were excellent.

Oceanfront 2 bed, 2 bath, kitchen with full AC!
The condo was very well equipped ......all beach gear you could need for sure . Also the fridge had all condiments and sauces as did the spice cupboard . Garbage bags , food wrap , storage containers etc...Come here first before you go to the supermarket on arrival or you will duplicate what is here ! Lots of parking . A/C worked flawlessly . Never heard the neighbours . Beautiful view ! Leonard even set us up to watch the Four Nations Cup when we couldn't get it . We were here a month and can honestly say we couldn't have found a better place to stay . I hope that when we come back to this beautiful island that we can stay at Leonard's place again !

On-the-Ocean; Stunning Corner Unit, Spacious, A/C!
We had a great time at Ineke’s place. The bed was really comfortable, the AC worked well and the view and sound of the surf were spectacular. The information and water gear they supplied really came in handy, too. We enjoyed their coffee in the mornings, as well. We would be happy to stay there again, should we return to the Big Island.

A/c & Ocean front pool, 1bedroom in heart of Kona
It is worth renting from an owner that is available and responsive! Tiffany was very great to deal with and very helpful. The place is very clean and very close to downtown. There are bikes for rent across the street. The seaside pool is amazing and relaxing with the waves crashing into the rocks just feet away. Thank you for the last minute stay!
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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