Book the Best Hotels with POOL in Wailea in 2026

Q: What are some accommodations with pools in Wailea?

Grand Wailea Maui, A Waldorf Astoria Resort : Resort, 9-minute walk from Wailea Beach. Features 9 outdoor pools, a children's pool, and a lazy river. Fairmont Kea Lani Maui : Resort, 11-minute walk from Wailea Beach. Offers 3 outdoor pools, a children's pool, and 6 restaurants. Four Seasons Resort Maui at Wailea : Resort, 6-minute walk from Wailea Beach. Provides 3 outdoor pools, a children's pool, and 3 restaurants. Wailea Beach Resort - Marriott, Maui : Resort, 10-minute walk from Wailea Beach. Features 4 outdoor pools, a children's pool, and 4 restaurants. Andaz Maui at Wailea Resort - a concept by Hyatt : Resort located near Wailea Beach. Offers 4 restaurants, 5 outdoor pools, and 2 pool bars.

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Our top choices for Wailea hotels with a pool

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Plunge into luxury at this adults-only resort with a serene outdoor pool and beach shuttle service.

CA $1,309 total

includes taxes & fees

Aug 1 - Aug 2

4 outdoor pools, pool umbrellas, sun loungers

Wailea Beach Resort - Marriott, Maui

Wailea

Dive into paradise at this Hawaiian resort with 4 outdoor pools, a waterslide, and poolside cocktail service.

CA $1,232 total

includes taxes & fees

Jul 31 - Aug 1

9 outdoor pools, cabanas (surcharge), sun loungers

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Splashy paradise with 9 pools, a lazy river, and oceanfront views awaits at this luxury Hawaiian resort.

CA $1,569 total

includes taxes & fees

Aug 14 - Aug 15

3 outdoor pools, cabanas (surcharge), pool umbrellas

Fairmont Kea Lani Maui

Wailea

Triple the tropical fun with 3 outdoor pools, cabanas, and a swim-up bar at this Hawaiian beachfront haven.

CA $1,765 total

includes taxes & fees

Aug 8 - Aug 9

Grand Champions

Wailea

Wailea resort offers serenity with sun-drenched pool and hot tub, perfectly situated by golf greens.

CA $720 total

includes taxes & fees

Jul 17 - Jul 18

Four Seasons Resort Maui at Wailea

Wailea

Splash into paradise at this beachfront resort with 3 outdoor pools, a swim-up bar, and a thrilling waterslide.

CA $2,583 total

includes taxes & fees

Aug 7 - Aug 8

Outdoor pool, free cabanas, pool umbrellas

Residence Inn by Marriott Maui Wailea

Wailea

Soak up the sun at this peaceful poolside oasis with free cabanas, hot tub, and just steps from Wailea Beach.

CA $818 total

includes taxes & fees

Jul 25 - Jul 26

5 outdoor pools, cabanas (surcharge), pool umbrellas

Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

Discover coastal luxury with 5 ocean-view pools where cabanas and loungers invite blissful relaxation beneath the Hawaiian sun.

CA $1,681 total

includes taxes & fees

Aug 16 - Aug 17

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Choose what matters most at hotels with a pool in Wailea

Breakfast included

4 stars

Price trends for hotels in Wailea

Less expensive	More expensive	Next month
September	May	CA $414

Month	Price
January	CA $876
February	CA $796
March	CA $572
April	CA $606
May	CA $1,117
June	CA $424
July	CA $524
August	CA $414
September	CA $400
October	CA $442
November	CA $474
December	CA $558

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Wailea. Select dates and complete search for nightly totals inclusive of taxes and fees.

Top Wailea Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

8/10 Good

"Overall, the Grand Wailea is a great hotel, however, as a guest you feel like you’re just a cog in the machine. We had a great time, but never felt that over the top service / experience that you would expect for a hotel with the reputation that it has / costs as much as it does"

Ho‘olei Villas at Grand Wailea

10/10 Excellent

"Overall, our stay at Ho’olei was wonderful, as always! We were a party of eight, and the three-bedroom villa was the perfect setup for our family. There was something for everyone to enjoy, especially the kids. We loved the fitness classes, the pools on both sides of the property, the dining options, and the Fourth of July festivities. The villa was spotless, spacious, and very comfortable. One of our favorite parts of the trip was enjoying dinner on the lanai while watching the beautiful sunsets—those are memories we'll always cherish. Thank you, Ho’olei, for another amazing stay. We can't wait to come back!"

Andaz Maui at Wailea Resort - a concept by Hyatt

8/10 Good

"Loved the property but definitely had difficulty with getting service poolside. Moved to a different pool and thought that would help. Still no service. Eventually moved back to adult pool and walked around and found a staff member. After that we just decided to go directly to the bar ourselves for a drink. I got the feeling they thought we weren’t staying there but they should ask. We were guests of the hotel. I would appreciate spending that kind of money per night to not have to seek out service."