Find and compare 5 Star hotels in Wailea

Name: Wailea Luxury Hilltop Resort Vistas
Rating: 10

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Featured Wailea 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

CA $1,038

CA $1,324 total

Oct 25 - Oct 26

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.8/10 Excellent! (1,014 reviews)

"The pools were wonderful, but the hours were short. It’s a long walk around the property to get to the pools but very beautiful. I found it to be a bit isolated and expensive, but really enjoyed our stay"

Reviewed on Oct 1, 2026

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

CA $1,174

CA $1,487 total

Oct 2 - Oct 3

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

9.6/10 Exceptional! (1,000 reviews)

"Incredible service and high end property. The rooms are updated with a nice balcony. 3 pools and direct beach access makes it easy."

Reviewed on Sep 24, 2026

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI

CA $858

CA $1,119 total

Oct 30 - Oct 31

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...

9/10 Wonderful! (1,001 reviews)

"Convenient location nd good staff at the concierge for tour bookings"

Reviewed on Sep 30, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

CA $1,503

CA $1,884 total

Oct 23 - Oct 24

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...

Hotel Wailea Maui

555 Kaukahi Street, Maui Kihei HI

Fully refundableReserve now, pay when you stay

CA $1,209

CA $1,519 total

Oct 31 - Nov 1

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...

9.4/10 Exceptional! (1,002 reviews)

"Everything was excellent, form the location to the incredible food!"

Reviewed on Sep 22, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

CA $2,476

CA $3,032 total

Oct 17 - Oct 18

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Wailea Beach and Grand Wailea ...

9.6/10 Exceptional! (54 reviews)

"Amazing property with an incredible staff. A+++ all the way around!"

Reviewed on Aug 25, 2026

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

CA $3,757

CA $4,559 total

Oct 13 - Oct 14

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free breakfast, free valet parking, and 3 outdoor pools. Popular attractions Wailea Beach and Polo Beach are ...

Villa, Garden View, 2-bedroom

3200 Wailea Alanui Dr Kihei HI

CA $921

CA $1,900 total

Oct 7 - Oct 8

includes taxes & fees

Book a stay at this luxury condo in Kihei. Enjoy free parking, a beach locale, and free grocery shopping service. Popular attractions Wailea Beach and Keawakapu ...

Wailea Luxury Hilltop Resort Vistas

10 Wailea Ekolu Pl Kihei HI

Book a stay at this luxury apartment in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located ...

10/10 Exceptional! (3 reviews)

"The best place while we in Hawaii. The first time we had a place with cool Ac . Nice view . Gotta to stay here guys. Big kitchen and clean everywhere. Awesome bathroom, the mirror with light and the view from kitchen.. Amazing❤️"

Reviewed on Aug 11, 2026

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent Wailea hotel reviews by fellow wanderers

AC Hotel by Marriott Maui Wailea

4 out of 5

Posted less than an hour ago

Travelocity Verified Review

"Only negative thing I have to say is the food wasn’t the best. There’s plenty of other places to go that are very close though."

A verified traveller stayed at AC Hotel by Marriott Maui Wailea

Grand Wailea Maui, A Waldorf Astoria Resort

4 out of 5

Posted 10 hours ago

Travelocity Verified Review

A verified traveller stayed at Grand Wailea Maui, A Waldorf Astoria Resort

Andaz Maui at Wailea Resort - a concept by Hyatt

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"We really enjoyed our stay. We booked 2 weeks but ended up leaving a couple days early because of the potential hurricane threat. Staff was amazing!! Everyone was so very friendly! Loved the walking path to other hotels, shops, restaurants! Rooms were nice, loved the coffee, chips, cookies, cute reusable bag provided. Wished it had another mirror somewhere to get ready while another was showering and wished there was more space for clothes. Though again we were there for 2 weeks so had a lot. They had full sized shampoo, conditioner, body wash, ironing board and cloths steamer, nice hair dryer and robes. Small reusable water bottles with ice and water available on each floor. Food by the pool was good. We rented a car for part of our stay, so super close to Kīhei for food, other beaches, shops but $60/day to park and had to use valet. Pools were beautiful! Reef safe sunscreen 30 & 50 were provided at every pool. We were a little disappointed that 2 pools were being worked on and we didn’t know it beforehand. Very noisy at one pool M-F for hours. And limited shady spots, and if windy, shade umbrellas had to come down. You could purchase cabanas in the shade for an extra $250 I believe but many sat empty at all pools. Beach was rough after the storm (can’t be helped because of weather) but no one was working on steps, path to get down to the beach. Other hotels were on it days after it happened… just something to be prepared, aware of. We were able to snorkel."

A verified traveller stayed at Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea Ekahi - CoralTree Residence Collection

5 out of 5

Posted 9 days ago

Travelocity Verified Review

"What a gorgeous complex! There was no "beach" at all and the main pool at the beach access was being renovated, so that was a bit of a bummer. BUT, we frequented another pool close to us which was very nice. The area was quiet, very clean and well maintained. We didn't have info in our condo regarding pool codes, WIFI, map of the area to find the 3rd pool or fitness center, so we were messaging a lot. Would have been helpful to have a little book of things to do, places to walk to, etc., in the condo. Condo itself (30D) was gorgeous, very comfortable and it was hard to leave. THANK YOU for a wonderful stay!"

A verified traveller stayed at Wailea Ekahi - CoralTree Residence Collection

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