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Our top choices for Wailea 5-star hotels

Property grounds
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 20.927.580 ₫
24.843.548 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Four Seasons Resort Maui at Wailea
9 outdoor pools, pool cabanas (surcharge), pool loungers
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, (1001)
"Awesome place to stay with kids "
United States
Sandeep
The price is 18.031.150 ₫
23.113.040 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Grand Wailea Maui, A Waldorf Astoria Resort
Exterior detail
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1006)
"Beautiful amenities and friendly staff! "
United States
Laura
The price is 22.576.779 ₫
28.353.936 ₫ total
includes taxes & fees
17 Jan - 18 Jan 2026
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 26.297.676 ₫
32.781.014 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Restaurant
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 52.828.056 ₫
64.421.409 ₫ total
includes taxes & fees
8 Jan - 9 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 89.475.276 ₫
107.092.350 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Fairmont Kea Lani Maui Villa Experience
Luxury Apartment | Beach/ocean view
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.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI
The price is 16.768.388 ₫ per night from 9 Jan to 10 Jan
16.768.388 ₫
21.676.114 ₫ total
9 Jan - 10 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
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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 12.064.258 ₫

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.