Holiday 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 favourite
Home in Keaau
4.93 out of 5 average rating, 30 reviews

Gorgeous Gated Retreat Near Ocean w Pool & Deck!

JasmineRating, 5 stars1 month ago
My family and I greatly enjoyed our time at the house. It had ample space and beautiful surroundings outside. We felt right at home here with everything we needed to cook together each day and even fun pool toys for our days outside. We would definitely return!
Top Guest favourite
Home in Kailua-Kona
4.99 out of 5 average rating, 120 reviews

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

TylerRating, 5 stars2 weeks ago
This was quite a charming place with supportive hosts. We enjoyed the frog song but some may find it loud. The property is rich in design elements and immersing you in the out doors. Local recommendations and flexible hosts made for an overall good experience.
Superhost
Home in Kailua-Kona
4.93 out of 5 average rating, 14 reviews

Big House with ocean view and private pool in Kona

MattRating, 5 stars1 week 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.
Guest favourite
Home in Kailua-Kona
4.91 out of 5 average rating, 142 reviews

Tropical Oasis Home with Pool and Steps to Beach

JuliaRating, 5 stars2 weeks ago
Our family's stay at Joe and Anna's home was excellent and perfectly set up for our three-generation group to enjoy a relaxing stay. The home has ample and comfortable indoor/outdoor communal space, was super clean, and is kept cool by fans throughout (and AC in bedrooms). Joe and Anna are very responsive hosts and have really thought about all the details. We really appreciated all of the thoughtful touches that made it super easy for us to explore the island (snorkelling gear, beach towels, chairs, and more) and the well-stocked kitchen. It was great to be in such a quiet and convenient location, with easy access to the nearby shopping centre with a grocery store and restaurants, and beaches/activities. This property is a real gem, and we hope to come back again!
Guest favourite
Home in Makaha Valley
4.91 out of 5 average rating, 100 reviews

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

JuliaRating, 5 stars5 days ago
The house is amazing, very well equipped, there is absolutely everything you need there from all sorts of kitchen appliances, grill stuff and beach equipment. The view is absolutely breathtaking. The house is beautifully furnished. Contact with Kristen was great, she was responding very quickly to all of our questions. I really, really recommend this house!!!!
Top Guest favourite
Home in Kailua-Kona
5 out of 5 average rating, 21 reviews

Home with Panoramic Ocean Views + Private Pool

AchalRating, 5 stars3 days 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 week 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!
Guest favourite
Home in Pepeekeo
4.87 out of 5 average rating, 165 reviews

Hamakua Coast Tropical Home

TandyRating, 5 stars6 days ago
What a great stay! Nice and private - the ocean view and sunrises were perfect! The porch and outdoor eating spaces were awesome. The house was clean and had everything we could think of that we’d need. And that pool was pretty snazzy, too! Everything was just perfect.

Condo rentals with a pool

Guest favourite
Condo in Kihei
4.92 out of 5 average rating, 148 reviews

Beach Area Condo

TracyRating, 5 stars6 days ago
What a great location! Karen’s condo was exactly as described, very clean, comfortable beds. We loved it so much we booked for next year. It is like a 4 minute walk to beach, she had beach chairs, toys and umbrella. There is a convenient outside shower in lower parking lot to wash off sand. We saw lots of whales breaching or tail slapping from beach, even a giant sea turtle would come sun itself. If you are planning on staying here, we found directions to actual condo confusing. We were hauling luggage and golf clubs up and down stairs. The easiest way to get to unit if you park in upper lot bring your luggage DOWN to The road to main entrance there is one set of steps to go down to unit.
Guest favourite
Condo in Lahaina
4.98 out of 5 average rating, 183 reviews

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

JordanRating, 5 stars2 weeks 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.
Guest favourite
Condo in Kailua-Kona
4.95 out of 5 average rating, 106 reviews

Royal Kahili Condo with Lanai Ocean View

PattiRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Kailua-Kona
4.93 out of 5 average rating, 147 reviews

2 Bedroom Penthouse Condo With Ocean View And Pool

SteveRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Kailua-Kona
4.99 out of 5 average rating, 121 reviews

Modern condo in Kona- Close to the ocean & dining

LukeRating, 5 stars1 week ago
Keisha's place was great. All instructions on how to find the place and get in were very clear and easy to understand. The place was squeaky clean and very nice. We enjoyed spending most mornings on the outside back patio area. It is a peaceful location, and within walking distance of numerous restaurants and attractions. Overall we were very pleased with our stay and we would recommend this place to anyone.
Guest favourite
Condo in Wailuku
4.89 out of 5 average rating, 114 reviews

Oceanfront Condo with Pool and Jacuzzi

Candace ErinRating, 5 stars3 weeks ago
Beautiful location. Easy check in.
Superhost
Condo in Koloa
4.89 out of 5 average rating, 102 reviews

LUX***NEW-Modern Spacious Condo &Amazing Balconies

SrinivasanRating, 5 stars1 week ago
Very good property but a little pricey especially for a non-peak season
Superhost
Condo in Kailua-Kona
4.78 out of 5 average rating, 134 reviews

A/c & Ocean front pool, 1bedroom in heart of Kona

ChadRating, 5 stars2 months ago
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!

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