Top Hawaii rentals with pool or private pool - United States of America

Popular Hawaii destinations on Stayz

Explore Hawaii rentals with pools

Aston Maui Kaanapali Villas

Sleeps 4

Premier Host

Oceanfront Home w/Private Pool. USA Military & Fire - Repeat Guest Discount!

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Premier Host

Ocean front~Pool,AC,Views,Spacious! Fall into whale season special 395 per night

Sleeps 10 · 4 bedrooms · 2 bathrooms

Top rated rentals with pools - Hawaii

Premier Host

Stunning yet quiet location.

Beautiful villa, convenient to beach, pool, carpark. Villa well stocked with everything you might need. Gorgeous outlook to beach. Mahalo

D L.

Stayed May 2025

Your own tropical paradise at Paradise Poipu

Premier Host

Lovely

Beautifully appointed house and garden in fantastic location, walking distance to Poipu Beach. Condiments left by/for guests is a nice touch.

Glenn D.

Stayed Dec 2024

Premier Host

Perfect Stay.

This was such a great place for our family of four older children. It was so beautiful to come back to after our day of touring the island sites. We were right on the beach and could look out over to the island beyond, watch the surfers and even dolphins going by. An afternoon swim was fabulous before a cocktail on our patio. The house was very well set up with everything we needed. We cooked most nights and just enjoyed being at the house. We had great communication with the owner and everything for check in ran smoothly.

Sally Y.

Stayed June 2019

Find spaces that suit your style

House

Condo/Apartment

Frequently asked questions

Are there any holiday rentals with a pool in Hawaii?

Choose from 23,041 holiday rentals with a pool around Hawaii. Take the family on a getaway to Kaanapali or check out other exciting cities like Poipu and Napili-Honokowai. Wherever you plan to go and whether you want to swim or just lounge by the water, Stayz has your ideal stay.

How much does it cost to stay in a holiday rental with a pool in Hawaii?

Exactly where you stay, what time of year you travel and your trip length will influence the price of a holiday rental with a pool in Hawaii. Enter your travel dates on Stayz, then pick the right one for you and get ready to make a splash.

When is the best time to book a holiday rental with a pool in Hawaii?

March is when most Stayz guests stay in a holiday rental with a pool in Hawaii. Spend your escape experiencing the buzz of this destination and relaxing by the water at your holiday rental. Demand is higher at this time of the year, so start planning early to get the best options.

What holiday rentals with a pool in Hawaii have nice views?

Use the "Location" filter to find a holiday rental with a pool and the views you'd love to wake up to. Start by entering the dates you plan to visit Hawaii, then narrow your search based on the sort of area you'd rather stay in. The only thing left is to pack your swimsuit and you're set for a splashing good time.

Are there holiday rentals with a private pool in Hawaii?

Choose a holiday rental with a private pool in Hawaii and enjoy a morning swim or midnight dip — or anytime you want! You'll be able to keep the kids easily occupied, and you'll never have to worry about sharing with other guests. Use our "Private pool" filter to discover your ideal holiday rental.

What are the top things to do in Hawaii?

Venture out and experience all that Hawaii has to offer from the comfort of your holiday home rental. It pays to do a bit of research on the things you'd like to do and see, so you can plan the perfect escape.

Why should I book my holiday rental with a pool with Stayz?

Stayz promises excellent customer support from the second you book until your adventure is over, so every aspect of your holiday is enjoyable and hassle-free. It's all part of our Book with Confidence Guarantee, which also includes deposit and payment protection and flexible cancellation policies. Another great thing about us? You can use our filters to narrow your search by budget, location, amenities and more. Whether you're looking for a pet-friendly property or an oceanside getaway for the family, we've got holiday rentals with a pool that meet your exact style and needs.