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Our top choices for Wailea 5-star hotels

Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1000)
"Beautiful property, efficient staff, truly a wonderful stay "
Canada
Angela
The price is 19.878.395 ₫
23.448.951 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Four Seasons Resort Maui at Wailea
7 restaurants, breakfast served
Grand Wailea Maui, A Waldorf Astoria Resort

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, (1000)
"Awesome place to stay with kids "
United States
Sandeep
The price is 17.004.219 ₫
21.768.560 ₫ total
includes taxes & fees
13 Dec - 14 Dec
Grand Wailea Maui, A Waldorf Astoria Resort
View from room
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1003)
"Beautiful amenities and friendly staff! "
United States
Laura
The price is 20.790.695 ₫
26.078.002 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Fairmont Kea Lani Maui
Outdoor spa tub
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1001)
"Great"
United States
Joseph
The price is 22.353.321 ₫
27.931.314 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor pool, pool loungers
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (44)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
United States
Leslie
The price is 48.205.766 ₫
58.934.256 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Ho‘olei Villas at Grand Wailea
View from property
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is 83.699.891 ₫
100.279.841 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Fairmont Kea Lani Maui Villa Experience
Luxury Apartment | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2)
"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 21.826.741 ₫ per night from 14 Dec to 15 Dec
21.826.741 ₫
27.300.143 ₫ total
14 Dec - 15 Dec
includes taxes & fees
9.2/10 Wonderful! (998 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.

Top Wailea Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in Wailea?
Grand Wailea Maui, A Waldorf Astoria Resort, Ho'olei Villas at Grand Wailea and Four Seasons Resort Maui at Wailea are among the leading 5-star hotels in Wailea, based on reviews by our guests. These upmarket hotels rate highly for things like their amenities, location and service standards. Pick your favourite and experience the best of it all.
How much does it cost to stay in a 5-star hotel in Wailea?
You can find several pricing options for 5-star hotels in Wailea on Expedia. How much you'll pay will depend on your holiday dates, length of your trip and other factors. Compare available properties for your desired dates and make use of our pricing and other filters to find the perfect high-end stay.

  • Search for the lowest price per night from 11.994.473 ₫

What makes a hotel 5 stars in Wailea?
In Wailea, a hotel is required to offer a specific level of high-end conveniences to be designated 5 stars. These may include gourmet restaurants, on-site gyms, saunas and spas, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their guest-centric service. You can look forward to things like nightly turn-down services, concierge services and in-room massages. Some may also offer thoughtful touches like welcome gifts.

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