Find and compare 5 Star hotels in Wailea

Start date: Check-in selected.
To Date
End date: Check-out

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

Featured Wailea 5 Star hotels

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
The price is CA $1,058 per night from Nov 21 to Nov 22
CA $1,058
CA $1,248 total
Nov 21 - Nov 22
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition ...
9.6/10 Exceptional! (999 reviews)
Great Service
Offered turn down service; the staff went above any beyond to ensure that we were comfortable.

Reviewed on Oct 26, 2025

Opens in a new windowFour Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
The price is CA $829 per night from Nov 30 to Dec 1
CA $829
CA $1,069 total
Nov 30 - Dec 1
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,003 reviews)
This resort is stunning! The view from our room was amazing! We stayed 8 nights and ate at all the restaurants. All were great. Nobu had the best sunset (make reservation for 30 mins prior to sunset and request the middle table out on the patio). The bar at Humuhumunukunukuapuaa is so cool! You’ll ...

Reviewed on Nov 8, 2025

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is CA $1,071 per night from Nov 29 to Nov 30
CA $1,071
CA $1,346 total
Nov 29 - Nov 30
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
9.4/10 Exceptional! (1,006 reviews)
We stayed at the Fairmont Kea Lani for our honeymoon and from the moment we arrived everything was perfect. The lei and kukui nut necklaces were so fun and check in was a breeze, we were even able to check in early. Our room was huge and the ocean view from our balcony was a beautiful way to wake ...

Reviewed on Nov 11, 2025

Opens in a new windowFairmont Kea Lani Maui
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
Fully refundableReserve now, pay when you stay
The price is CA $1,177 per night from Nov 30 to Dec 1
CA $1,177
CA $1,472 total
Nov 30 - Dec 1
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our ...
9.2/10 Wonderful! (1,001 reviews)
Lovely room and property, friendly staff, excellent amenities (on site dining, shuttle service, beautiful pool and hot tub.) Offers a more secluded, romantic and quieter Maui experience than the typical Wailea lodging. Unique Birdcage Restaurant and bar was an added plus for us.

Reviewed on Nov 6, 2025

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle, Kihei, HI
The price is CA $2,559 per night from Nov 21 to Nov 22
CA $2,559
CA $3,110 total
Nov 21 - Nov 22
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Wailea Beach and Shops at Wailea ...
9.6/10 Exceptional! (43 reviews)
Perfect for Families. Quite spacious and great for a relaxing Family vacation.

Reviewed on Jun 15, 2025

Opens in a new windowHo‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

5 out of 5
4100 Wailea Alanui Dr-Building A, Kihei, HI
The price is CA $4,202 per night from Dec 15 to Dec 16
CA $4,202
CA $5,039 total
Dec 15 - Dec 16
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy free breakfast, free valet parking, and 3 outdoor pools. Popular attractions Wailea Beach and Polo Beach are ...
9.6/10 Exceptional! (6 reviews)
It’s a decent hotel to stay for the family.

Reviewed on Aug 22, 2024

Opens in a new windowFairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas

5 out of 5
10 Wailea Ekolu Pl, Kihei, HI
Stay at this 5-star luxury apartment in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located ...
We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back!

Reviewed on Nov 28, 2024

Opens in a new windowWailea Luxury Hilltop Resort Vistas
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