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Check availability on Wailea 5 Star Hotels

Tonight
May 5 - May 6
Tomorrow
May 6 - May 7
This weekend
May 8 - May 10
Next weekend
May 15 - May 17

Our top choices for Wailea 5-star hotels

9 outdoor pools, cabanas (surcharge), sun loungers

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)
"Perfect location for day drinking "
United States
William
The price is ￥140,765
￥177,339 total
includes taxes & fees
May 19 - May 20
Grand Wailea Maui, A Waldorf Astoria Resort
Exterior detail

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,001 reviews)
"Beautiful place"
United States
Laci
The price is ￥173,334
￥215,130 total
includes taxes & fees
Jun 5 - Jun 6
Fairmont Kea Lani Maui
Property grounds

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)
"Wonderful Hotel Great restaurants staffed by true professionals "
United States
John
The price is ￥133,273
￥158,212 total
includes taxes & fees
May 25 - May 26
Four Seasons Resort Maui at Wailea
Outdoor spa tub

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,002 reviews)
"We had a good time. Comfortable hotel. "
United States
andrea
The price is ￥121,939
￥154,119 total
includes taxes & fees
May 19 - May 20
Hotel Wailea, Relais & Chateaux - Adults Only
Restaurant

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (46 reviews)
"This was a beautiful villa across the street from the grand wailea. Booking included full use of the resort, which was excellent. Included was a shuttle service with uber-like app that we could use to go anywhere within a 1 mile radius. This was a great stay"
United States
Daniel
The price is ￥267,141
￥327,329 total
includes taxes & fees
May 11 - May 12
Ho‘olei Villas at Grand Wailea
View from property

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is ￥534,391
￥643,616 total
includes taxes & fees
Jun 1 - Jun 2
Fairmont Kea Lani Maui Villa Experience
Luxury Apartment | Beach/ocean view

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas
Condo (4 Bedrooms) | View from room

Wailea Elua Collection by KBM - 2 Units (2009/2103)

Wailea Elua Collection by KBM - 2 Units (2009/2103)
5.0 star property
Kihei
Wailea Elua Collection by KBM - 2 Units (2009/2103)
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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.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI
The price is ￥137,059 per night from May 29 to May 30
￥137,059
￥173,751 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (1,003 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

Top Wailea Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent
"Pool was Great"
David 2-night trip
Posted 1 day ago
Grand Wailea Maui, A Waldorf Astoria Resort

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 ￥96,866

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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