A beach with clear turquoise water, people sunbathing and swimming, and a mountain in the background.

Find 5 Star Hotels in Wailea, HI from ￥89,103

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Check availability on Wailea 5 Star Hotels

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Wailea 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.8 out of 10, Excellent, (1,006 reviews)
"Beautiful hotel, great amenities, so many pools and fun things and beach access, restaurants, bar, will definitely go back!"
United States
Seyed Kamyar
The price is ￥108,819
￥139,519 total
includes taxes & fees
Dec 5 - Dec 6
Grand Wailea Maui, A Waldorf Astoria Resort
A staircase with a view of a garden, palm trees, and a bridge.

2. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,002 reviews)
"Great place to stay with the family."
United States
Iulian
The price is ￥155,025
￥195,125 total
includes taxes & fees
Dec 1 - Dec 2
Fairmont Kea Lani Maui
A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

3. Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,001 reviews)
"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"
United States
Quinn
The price is ￥130,639
￥165,424 total
includes taxes & fees
Nov 7 - Nov 8
Four Seasons Resort Maui at Wailea
A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.

4. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
5.0 star property
Wailea
9.0 out of 10, Wonderful, (1,000 reviews)
"Not sure if you can beat the pools, value, location, views, snorkel, and staff on the island! Loved our stay!"
United States
Rachel
The price is ￥86,377
￥113,641 total
includes taxes & fees
Nov 29 - Nov 30
Wailea Beach Resort - Marriott, Maui
A poolside area with a fire pit, lounge chairs, and umbrellas.

5. Hotel Wailea Maui

Hotel Wailea Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,002 reviews)
"Spacious and updates rooms with everything you need. The service is simply outstanding. The pool was never crowded. The food at the restaurants was so good!"
United States
Maureen
The price is ￥151,858
￥189,674 total
includes taxes & fees
Nov 18 - Nov 19
Hotel Wailea Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

6. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (54 reviews)
"The room was beautiful the view incredible , the amenities were perfect. I would stay again and again"
United States
Risa
The price is ￥272,549
￥333,821 total
includes taxes & fees
Dec 1 - Dec 2
Ho‘olei Villas at Grand Wailea
A resort pool area with a hot tub, lounge chairs, and palm trees.

7. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
Villa, Garden View, 2-bedroom
A modern kitchen with white cabinets, stainless steel appliances, and a large island.

8. Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (3 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Wailea.
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr Kihei HI
The price is ￥133,117 per night from Nov 7 to Nov 8
￥133,117
￥169,117 total
Nov 7 - Nov 8
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
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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.

Learn more about Wailea

Indulge in Hawai’i’s high life with a stay in this beautiful coastal area known for its luxury accommodation and secluded beaches.

See all hotels in Wailea
A golf course with a view of the ocean and a mountain in the distance.

Top Wailea Hotel Reviews

Hotel Wailea Maui

Hotel Wailea Maui

10/10 Excellent
"This place was top tier. From the service to the cleanliness and aesthetics. Highly recommend!"
Brad 5-night trip
Posted 3 hours ago
Hotel Wailea Maui

Frequently asked questions

What are the best 5-star hotels in Wailea?
Get set for 5-star luxuriousness at Grand Wailea Maui, A Waldorf Astoria Resort, Ho'olei Villas at Grand Wailea or Four Seasons Resort Maui at Wailea. These are among the best stays in Wailea according to Expedia guest reviews. Pick your favorite and get a taste of the finer life!
How much does it cost to stay in a 5-star hotel in Wailea?
There are a range of pricing options for 5-star hotels in Wailea on Expedia. How much you'll pay will depend on when you plan to travel, length of your trip and other factors. Compare available properties for your preferred dates and make use of our pricing and other filters to lock in the perfect high-end stay.

  • Search for the lowest price per night from ￥89,103

What makes a hotel 5 stars in Wailea?
Outstanding guest service is the hallmark of every 5-star hotel in Wailea. From the minute you arrive, staff ensure your every need is met, whether recommending activities and tours or providing in-room massage treatments. In addition, hotels must feature superior amenities to be considered for a 5-star rating. These can include luxury toiletries, saunas or spas, pools, gourmet kitchens and knowledgeable concierge.

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