Explore top 2026 5 Star Hotels in Wailea

Name: Wailea Luxury Hilltop Resort Vistas
Rating: 10

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Top Wailea 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$813 nightly

$965 total

Oct 25 - Oct 26

Total with taxes and fees

A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. There's fun for all ages with a lazy river and a children's pool, ...

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$1,080 nightly

$1,282 total

Oct 19 - Oct 20

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. There's fun for all ages with a free kid's club and a children's ...

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

$646 nightly

$767 total

Oct 25 - Oct 26

Total with taxes and fees

A full-service spa, 4 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's pool and a waterslide, ...

9/10 Wonderful! (1,002 reviews)

"Loved this hotel resort better than Gran Wailea! Jahdiel at the pool was so friendly and helpful every day! Love Jahdiel!"

Reviewed on Oct 3, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,118 nightly

$1,327 total

Oct 23 - Oct 24

Total with taxes and fees

A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's ...

Hotel Wailea Maui

555 Kaukahi Street, Maui Kihei HI

$840 nightly

$997 total

Oct 31 - Nov 1

Total with taxes and fees

This luxury resort includes 3 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, ...

9.4/10 Exceptional! (1,000 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

$1,777 nightly

$2,110 total

Oct 17 - Oct 18

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, ...

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

$2,698 nightly

$3,203 total

Oct 24 - Oct 25

Total with taxes and fees

A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with beach cabanas ...

Villa, Garden View, 2-bedroom

3200 Wailea Alanui Dr Kihei HI

$1,319 nightly

$1,565 total

Oct 19 - Oct 20

Total with taxes and fees

This condo features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A coffee shop, a terrace, ...

Wailea Luxury Hilltop Resort Vistas

10 Wailea Ekolu Pl Kihei HI

This apartment features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.

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

Get rates

Don't see what you're looking for?

See all available properties in Wailea

View all properties

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

Wailea Beach Resort - Marriott, Maui

5 out of 5

Posted 16 hours ago

Travelocity Verified Review

"Loved this hotel resort better than Gran Wailea! Jahdiel at the pool was so friendly and helpful every day! Love Jahdiel!"

A verified traveler stayed at Wailea Beach Resort - Marriott, Maui

Andaz Maui at Wailea Resort - a concept by Hyatt

5 out of 5

Posted 6 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 traveler stayed at Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea Ekahi - CoralTree Residence Collection

5 out of 5

Posted 11 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 traveler stayed at Wailea Ekahi - CoralTree Residence Collection