
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

Exceptional Oceanview Home - Pool & Stunning View
Lee’s home is perfect in every way imaginable. Our family of four had a spectacular vacation. We are already planning our next stay.

Stunning Serene Bali Retreat [Pool/AC/Ocean View]
Where do I even start? What a magical home with lush landscaping. Waking up to large windows that look out to the ocean was priceless. The location was quiet and safe and close to many activities we wanted to do in Kona. The beds were very comfortable as well. The pool was nice to cool off in after a long day but keep in mind it is not heated so depending on the time of day or sunlight it may be too cold for some. Also, being in such a lush tropical landscape with a large natural area behind the house there are birds and frogs making noise in the evening, which can be calming to some (like us) or can be too loud for others. When we visit the Big Island again this would be number 1 option for our stay.

Tropical Oasis Home with Pool and Steps to Beach
Our family ranging from 77 to 7 all agreed that the house exceeded our expectations. We appreciated the quiet setting with lots of places to walk {I think grandpa, walked them all}, the fully equipped kitchen, and the pool (of course). My grand daughter named the resident geckos and gave them all a fond goodbye. We had to drag our 16-year old off Magic Sands beach. We all enjoyed several snorkeling spots and splurged on a Fair Winds "Kona’s Best Morning Snorkel: Captain Cook & Kealakekua Bay." Many thanks.

Private Pool - 180° Ocean View - Minutes to Beach
We had a wonderful 7 day stay. Our 3 boys (16, 13, and 10) spent hours on the diving board and in the pool. Sandra’s place had everything we needed for beach trips, including beach chairs, wagon, umbrella, cooler and beach towels. I was so happy to have a washing machine to wash out the sandy towels and suits after our beach trips. It was a 5-10 minute trip for Costco,-target and Walmart and a 30-40 minute trip to Hāpuna Beach (don’t miss the Malsada stand on the highway on your way). We would come back to the house to cook supper, swim more in the pool, and watch the sunset from the beautiful yard. We also got a lot of use out of the basketball net in the driveway, and volleyball net in the side yard. Sandra was extremely helpful with all aspects of our stay, including local recommendations. Would definitely stay again if on the Big Island!

Tiny House Hawaii
Marilyn's place is flawless. My husband and I have been booking places through airbnb for a while and this was definitely the best one ever. I am very picky with cleanliness, and this place was spotless. Craig the home caretaker made sure to gave us all the information we needed, show us around, besides being super nice and friendly. The view from this tiny house was incredible, the place was exactly like the pictures, comfortable and had everything we needed. Marilyn's hospitality was amazing. She left us fresh fruit from her garden and a delicious cake on the fridge for when we arrived. Both Craig and Marilyn made us feel welcomed and made our experience perfect. We hope to come back someday.

Private Pool & Spa-Beautiful Oceanview Home
We really enjoyed the time we spent at this home! The views from the decks are amazing! The pool and hot tub are great and we especially enjoyed the AC and large TVs when we came in at night.

Big Family Home, Pool, Views, Yard, Lanai, Clean!
The house, which is very spacious, is located in a quiet residential neighborhood (the only real noise is from the many birds), which is five minutes from a grocery store and some restaurants in Waikoloa Village, and there are many restaurants, beaches, and things to do within a 30-minute drive; downtown Kailua-Kona is 45 minutes, and Volcanoes National Park and Hilo are about two hours (but easy driving everywhere, except for typical urban traffic congestion in Kona). The landscaping is amazing, and the backyard with a swimming pool is extremely private. It is also west-facing, so you get gorgeous sunsets with a slight ocean view (the property is inland). The AC units (for which there is an extra charge) are only in the bedrooms, so the house gets stuffy during the day, but cools off quickly in the evening. We had one minor maintenance issue, but the host, Andy, was responsive and addressed it quickly. We would definitely return if we have a future trip to the Big Island.

Ocean, Sunset, Mountain & Celestial Views
Tarek was awesome. Super responsive and very kind. 10/10 recommend his place to stay at when visiting Big Island. House was packed with much needed living amenities (paper towels, board games, laundry facilities). Loved the living conditions I got the chance to stay in!
Apartment rentals with a pool

Ocean Front Kona Reef A35! It doesn't get better!
Wendy’s place was amazing for us. We loved watching the surfers in the morning while we drank our coffee. The bed was comfortable and the shower was great! One day we took an uber to the beach and used the chairs and umbrella. They were great! My husband is a larger man and fit nicely in their beach chairs. Another thing to note is there location. It’s walkable to town but down the road so you get that peace and quiet. We had an amazing time and would recommend staying here!

Kona Nate's Ocean View Escape
Would stay here again! The view was perfect, great location, and very comfortable. The messages were proactive and made us feel so welcome. We had everything we needed during our stay and so so appreciate the space being available!

OnOcean! Sale! AC Beachgear Pool ParkFree Elevator
Jan and Cami were very nice to deal with. Their condo is in an amazing location. They thought of everything to make their guests comfortable. Very well organized space. It was clean and inviting.

Inna's Downtown-Walk to Beach and to Supermarket!
We loved staying at Inna’s place! Having extra beach towels, sunscreen, umbrella, etc were so helpful when we went out and explored the area. The location itself is very walkable and tucked away from downtown. We also loved the fully stocked kitchen and washer/dryer!

Keauhou Garden - Ocean view - Walk to Harbor
Thank you Dominique and Fabio for everything. Your place is truly stunning we had such a perfect time. The beach gear was so much fun for our beach days, the location was great and close to pretty much everything we wanted to do on the trip, we loved our morning coffee on the lanai, and the decor was a plus, loved it all! We also got engaged on this trip and I will never forget it. ❤️ Mahalo

Ali'i Dr w/ Ocean Sunsets next to Farmer's Market
The condo was perfect for our family of four with two older teens. The third bed is a fold down couch. My kids took turns sleeping on it and both said it was pretty comfortable considering it was a fold down couch. The kitchen was well supplied and all the extra towels were very much appreciated. The pool is salt water, not chlorine. We would definitely recommend this condo to friends/family and stay there again. BTW hosts were amazing! Very prompt replies and very easy to work with.

Spectacular View, Direct Oceanfront Kona,Top Floor
Awesome location and lodgings. The soothing sounds of the ocean are the best.

Renovated Oceanfront Penthouse in Kona with AC
Thank you for a Beautiful condo and experience! The view is Awesome! The Complex is a great placement for a mixture of sandy beaches, tide pools, and surf. The condo has great placement in the complex for accessibility to elevator, pool and amenities. Stephanie’s condo will make you feel right at home with housewares, extra beach accessories, A great welcome and suggestion book for the island and overall organized, tidy surroundings! Donna and I Loved our stay
Quick stats about holiday rentals with a pool in Kailua-Kona
Total rentals
1.9K properties
Nightly prices starting at
₹4,328 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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- Hapuna Beach
- Kaunaoa Beach
- Kohanaiki Private Club Community
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- Mauna Kea Golf Course
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- Kealakekua Bay State Historical Park
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- Waikoloa Beach Golf Course
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- Mauumae Beach
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