Vacation rentals with a pool in Hawaiian Islands

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Popular amenities for Hawaiian Islands rentals with a pool

House rentals with a pool

Guest favorite
Home in Keaau
4.94 out of 5 average rating, 33 reviews

Gorgeous Gated Retreat Near Ocean w Pool & Deck!

KelseyRating, 5 stars1 week ago
Our family loved staying here! The kids thoroughly enjoyed the pool and exploring the grounds finding lizards, snails and birds. The house was clean and spacious and the a/c and fans were appreciated! We hiked to Shipman beach from the house and it was well worth it - saw lots of huge turtles and enjoyed a quick swim before heading back. Highly recommend staying here!
Top guest favorite
Home in Kailua-Kona
4.99 out of 5 average rating, 126 reviews

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

IlanaRating, 5 stars1 week ago
Beautiful home with amazing views! Plenty of room for our family of 6 and a well equipped kitchen and barbecue tools. Highly recommend!
Superhost
Home in Kailua-Kona
4.81 out of 5 average rating, 16 reviews

Big House with ocean view and private pool in Kona

DavidRating, 5 stars1 week ago
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!
Guest favorite
Home in Kailua-Kona
4.91 out of 5 average rating, 146 reviews

Tropical Oasis Home with Pool and Steps to Beach

MaryRating, 5 stars1 week ago
We had the dream family trip of a lifetime. The kids loved the pool—morning, noon and evening except when we went off on adventures. The neighborhood was quiet and within walking distance of a rocky beach. The house was roomy and well stocked with two large, long dining tables, one indoors and the other on an enclosed porch outdoors. Perfect for family dining. Joe and Anna were lovely hosts, pleasant and informative. We’d definitely recommend this home to anyone.
Guest favorite
Home in Makaha Valley
4.91 out of 5 average rating, 105 reviews

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

SaraRating, 5 stars1 week ago
We would absolutely stay here again. Poka'i Bay Beach was awesome for our small kids and only 14 min away. We loved the house and yard.
Top guest favorite
Home in Kailua-Kona
5 out of 5 average rating, 22 reviews

Home with Panoramic Ocean Views + Private Pool

AchalRating, 5 stars1 month ago
Great stay. We were a family of 4 with plenty of space to stretch out comfortably along with an excellent, well stocked kitchen that opened to a wide open den with amazing views of the ocean. Very central location that was easy from an exploring/activities standpoint. Pool was nice to have access to and great for ambiance. It was more for quick dips than lounging due to temp (not much of a difference with heating it in early March). Den opened to pool deck with great views. Master bath was dated as others have noted, but not an issue for us. No issues with not having AC in early March. There was a rental unit on premises with a single individual who came and went without bothering us, could be an issue for some. Made us think twice about leaving the kids home alone. We would definitely stay here again. Great for groups of 4-6 who like independence and value space.
Superhost
Home in Kailua-Kona
5 out of 5 average rating, 3 reviews

Oceanview Oasis + Pool + A/C

GarethRating, 5 stars1 month ago
Naomi’s place is beautiful, peaceful, and spacious. The lanai is an exotic and fun feature and the house is full of character. Tropical frogs serenade at night time while the morning starts with beautiful bird song and a view of the ocean. Meanwhile, beaches, restaurants, and shops are only a 5-10 minute drive away. When you stay in the house though, you feel as though you have escaped the hustle and bustle of day to day life. I stayed here with my wife, two young children, and in-laws. It was a fantastic time and I will always remember it!
Superhost
Home in Koloa
4.81 out of 5 average rating, 26 reviews

koolkondo Hula Bungalow with Pool by the beach

TracyRating, 5 stars2 weeks ago
Great location in Poipu and an easy walk to the beach. Never had to worry about parking at the beach which was a huge plus for this popular location. Multiple restaurants walkable and wagons with chairs and umbrella made it an all around full service experience. The beds and pillows were very comfortable including the pullout bed. The pool area is right outside the door with lounge chairs to start and end your day. We truly loved our time here. We can’t wait to come back. Thank you

Condo rentals with a pool

Superhost
Condo in Kihei
4.91 out of 5 average rating, 151 reviews

Beach Area Condo

ManojRating, 5 stars1 week ago
Karen is an excellent Host. The Apartment is perfect, modern, great location, well equipped, there are plenty of restaurants in walking distance but yet the Apartment is in a peaceful location. There is a beautiful beach literally minutes away. Can't wait to come back.
Top guest favorite
Condo in Lahaina
4.98 out of 5 average rating, 184 reviews

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

JordanRating, 5 stars1 month ago
Wish we could have stayed longer. Place was so clean, convenient location in the building and easy in and out access to explore the surrounding areas. We felt right at home. Loved the balcony views. Washer and dryer are big and nice, perfect for us between stops on different islands. Kelly was super nice, communicative and responsive! Would absolutely come back.
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 stars2 weeks 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 stars5 days 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
4.98 out of 5 average rating, 124 reviews

Modern condo in Kona- Close to the ocean & dining

JaniceRating, 5 stars3 weeks ago
The home was very clean and well organized and had everything we needed. The location was great and was close to the beach, Walmart, Costco and restaurants. Keisha was very helpful and she was quick to respond to any questions we had. We would love to return and stay at Keisha’s place again!
Guest favorite
Condo in Wailuku
4.89 out of 5 average rating, 118 reviews

Oceanfront Condo with Pool and Jacuzzi

AngelaRating, 5 stars1 week ago
The view from the patio was breathtaking! The condo was spotless when we arrived and we found everything we needed for the stay. We had a question about the TV streaming and got a response quickly. The TV is set up for Netflix and Prime Video, but you need to log into your own own account so remember to bring your information. When we were there in the afternoon one day, a couple of big turtles came onto the small beach. If we had been there a week earlier, we could have seen the whales in the bay since it was time for them to head back north. We always found parking right outside the door. It was easy to get our parking permit. When we went into the office to get it, nobody was there but a basket with tags was available. Just fill out the form with your information and take one to use for the duration of your trip. We felt like the location of the condo was perfect for us. Four days gave us plenty of time to see the entire island.
Guest favorite
Condo in Naalehu
4.87 out of 5 average rating, 110 reviews

Turtle Paradise at Punalu'u Black Sand Beach

KhuanRating, 5 stars2 weeks ago
Instructions for location and check-in were easy. We enjoyed cooking breakfast and eating it on the lanai. We also saw geckos! Getting to black sand beach was easy. We gave our 3 year old the bedroom and slept on the pull out couch. Both beds were comfy. Beach toys, coolers, snorkel gear was a huge plus!!

Home rentals with a private pool

Guest favorite
Home in Kihei
5 out of 5 average rating, 73 reviews

Your Own Private Resort with Breathtaking Ocean Views

PatrickRating, 5 stars3 months ago
Don’t pass up an opportunity to rent this house from Troy and Dianna! We have stayed at many rentals around the world and this one is top notch. House was clean, spacious, and kitchen well stocked with plenty of cook ware to cook some meals at home. Spent most of our time outside at the pool and hot tub. Beautiful views of ocean and nearby islands. Outside grill was cleaner than my grill at home. Wonderful outdoor scene. Plenty of beach equipment for beach excursions. There literally wasn’t anything needed at this house. Centrally located between Kihei and wailea. Closer to wailea shopping and restaurants than Kihei. Amazing beaches (Big Beach and Maluaka are our favs) within 10 minutes drive. Absolutely love the location.
Condo in Honolulu
3.8 out of 5 average rating, 15 reviews

Waikiki Banyan Condo, Diamond Head & Beach View

ChristopherRating, 5 stars14 months ago
Very clean. Good location.
Condo in Honolulu
4.33 out of 5 average rating, 9 reviews

Waikiki Banyan Condo One Block to Waikiki Beach!

DirkRating, 5 stars10 months ago
My wife and I enjoyed our stay. The location is great as far as walking to the beach, restaurants, and stores in the area. We love Waikiki thank you! Dirk
Superhost
Home in Kihei
4.93 out of 5 average rating, 30 reviews

Oceanview Home with Private pool and hot tub

JennieRating, 5 stars1 day ago
Steve’s place is great and he is an excellent communicator and very invested in ensuring his guests have a great experience. We loved watching the sunset from the deck and the pool and game room were both so fun for our family. Lots of pantry staples on hand as well as some yummy snacks to greet us. The location is private and peaceful and we loved all the beautiful Hawaiian plants and geckos in the yard. Thanks for a great stay!
Top guest favorite
Home in Pāhoa
4.94 out of 5 average rating, 430 reviews

Romantic Dodecagon Retreat Near a Black Sand Beach

JessicaRating, 5 stars3 days ago
Absolutely beautiful stay. The house is beautiful, the pool was incredible, and it was fantastic being so close to the coast. The kitchen was equipped with the basics for cooking, which was very helpful! The host was super communicative of anything going on as well, which made for an exceptionally pleasant stay. I would absolutely come back and stay here the next time I return to Hawaii. The listing is pretty accurate, you do need to travel quite a bit for groceries or other amenities. I think it was absolutely worth it.

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