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

🌴 Gorgeous Oceanfront Luxury Retreat 🌊 private pool, black sand beach, pond, AC

Sleeps 9 · 4 bedrooms · 3+ bathrooms

Top rated rentals with pools - Hawaii

Premier Host

Great little apartment!

Clean, comfortable apartment, everything needed for an enjoyable holiday on Maui’s West coast. Very easy communication with the owner. All staff at Papakea friendly and helpful. A great holiday, thank you Dawn!

Beth K.

Stayed July 2024

Premier Host

Didn’t want to leave

This property is fantastic. The kitchen is well stocked, the water equipment eg snorkels greatly appreciated. 40 mins drive from Kona so it is well and truly far from the crowds. The beach is lovely and a pleasant stroll past fishponds. Access to restaurants at Mauna Lani and “The Shops” is great. The golf course was also beautifully presented and very enjoyable to play. (North) . Sitting on the Lani, enjoying the beautiful gardens and fishpond with ocean in the background so relaxing. Would love to return here

Liz W.

Stayed June 2023

World Class Oceanfront Ko Olina Beach Villa Resort view from 7th floor lanai

Premier Host

Perfection

CQ's 3 bedroom condo was perfect for us. All the photos are a true representation of what you get. We loved the quiet location of Ko olina, being away from Waikiki suited us. Our kids loves the pools and lagoon, and would have spent all day every day in if we let them. Shane was a great help in answering all our questions on arrival and departure. Not only would we come back again, but also recommend to our friends and family. If you are looking for a relaxed, perfectly maintained, friendly environment for your vacation, CQ's place should be your first pick. Thank you for sharing your place.

Lauren G.

Stayed Nov 2017

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Frequently asked questions

Are there any holiday rentals with a pool in Hawaii?

Choose from 23,519 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.