
Holiday 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 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!

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 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).
Apartment 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
Once again, we enjoyed our stay at David's Place. We took more advantage of the pool this time. The convenience of being within easy walking distance to the center of Kona, cannot be overstated. The closeness of a supermarket and the smoothies at Loco Wraps was especially appreciated. Until next time, Thanks David!

2 Bedroom Penthouse Condo With Ocean View And Pool
We really enjoyed the condo and the views were out of this world. The building was quiet, we never heard neighbors, and the building was upkept. We stayed for 8 days, frequently hauling loads of either groceries or "stuff" and were thankful that there was an elevator to assist in the frequent trips to the car. The car parking space is located beneath the building in the shade, which was very nice to not have to get into a hot car each day. The condo was very clean and there were lots of little extras provided. There were lots of options for borrowing snorkeling masks and goggles, swim fins and even a beach umbrella. We packed lunches every day and we were thankful for the cooler options allowing us to pack what we needed to keep cool. Listening to the waves at night outside the master bedroom was very peaceful. We would wake up early and watch the surfers out each morning in front of the condo. Very relaxing trip. Our host was very responsive to questions and we would go back!

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 Kona property was a perfect launchpad for our Big Island adventures vacation, and an even better crash pad to recover in between outings! It is exactly as described, in a great location, very well provisioned with linens, beach gear, and a full kitchen with everything you need. Beds are comfortable and A/C and fans are great. Leonard is friendly and hospitable with great local advice. Very easy access to all things Kona and Big Island. Highly recommend for your EatSleepPlay Kona vacation!

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 holiday rentals with a pool in Kailua-Kona
Total rentals
1.6K properties
Nightly prices starting at
£39 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
- Kona Country Club
- Kohanaiki Private Club Community
- Pōhue Beach
- Kealia Beach
- Pololū Beach
- Kaluhikaa Beach
- Ke‘EI Beach
- Kuki’o Golf & Beach Club
- Mahaiʻula Beach
- Volcano Golf and Country Club
- Mauna Lani Golf
- Makalawena Beach
- Makolea Beach
- Pahoa Beach
- Mauumae Beach
- Two Step
- Mauna Kea Golf Course
- Beans Beach
- Honokohau Beach
- Waikoloa Beach Golf Course
- Kalāhiki Beach
- Wawaloli Beach
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