Vacation 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

Top guest favorite
Home in Keauhou
5 out of 5 average rating, 89 reviews

Mollie’s Paradise Resort Home - No Cleaning Fee!

YvonneRating, 5 stars5 days ago
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!!
Superhost
Home in Waimea
4.71 out of 5 average rating, 7 reviews

Beautifully Furnished 4 Bdrm Home At KaMilo w/Pool

SallyRating, 5 stars5 months ago
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.
Superhost
Home in Kailua-Kona
4.8 out of 5 average rating, 15 reviews

Big House with ocean view and private pool in Kona

MattRating, 5 stars1 month ago
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.
Top guest favorite
Home in Kailua-Kona
4.95 out of 5 average rating, 155 reviews

Private Pool - 180° Ocean View - Minutes to Beach

KarlRating, 5 stars1 month ago
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.
Superhost
Home in Kailua-Kona
5 out of 5 average rating, 4 reviews

Walua Oasis 2/2 Private Pool

StephanieRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Waikoloa Village
4.88 out of 5 average rating, 137 reviews

Big Family Home, Pool, Views, Yard, Lanai, Clean!

SaraRating, 5 stars2 months ago
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!
Top guest favorite
Home in Kailua-Kona
4.97 out of 5 average rating, 190 reviews

Halia Hale

DerekRating, 5 stars1 month ago
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).
Superhost
Home in Captain Cook
4.93 out of 5 average rating, 106 reviews

Beautiful Home With Private Pool on Kealakekua Bay

NeilRating, 5 stars2 months ago
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

Guest favorite
Condo in Kailua-Kona
4.94 out of 5 average rating, 54 reviews

Kona by the Ocean

ElizabethRating, 5 stars3 months ago
A beautiful clean condo. Great location. Loved the pool and hot tub and the ocean views from the grounds
Top guest favorite
Condo in Kailua-Kona
4.95 out of 5 average rating, 108 reviews

Royal Kahili Condo with Lanai Ocean View

Joongeol KimRating, 5 stars1 week ago
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.
Superhost
Condo in Kailua-Kona
4.79 out of 5 average rating, 105 reviews

Stylish Condo with pool-10 minute walk to ocean

MishaalRating, 5 stars1 day ago
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!
Guest favorite
Condo in Kailua-Kona
4.93 out of 5 average rating, 150 reviews

2 Bedroom Penthouse Condo With Ocean View And Pool

NancyRating, 5 stars3 weeks ago
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!
Top guest favorite
Condo in Kailua-Kona
4.95 out of 5 average rating, 81 reviews

Oceanfront complex at Casa de Emdeko unit #102

BrianRating, 5 stars2 weeks ago
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.
Superhost
Condo in Kailua-Kona
4.78 out of 5 average rating, 124 reviews

Beach Paradise

GeorgeRating, 5 stars1 month ago
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!
Guest favorite
Condo in Kailua-Kona
4.95 out of 5 average rating, 83 reviews

Oceanfront 2 bed, 2 bath, kitchen with full AC!

KooroshRating, 5 stars5 days ago
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.
Guest favorite
Condo in Kailua-Kona
4.97 out of 5 average rating, 136 reviews

On-the-Ocean; Stunning Corner Unit, Spacious, A/C!

ShashankRating, 5 stars2 weeks ago
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

Destinations to explore

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  5. Kailua-Kona
  6. Rentals with pools