Find and compare 5 Star hotels in Wailea
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Featured Wailea 5 Star hotels
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
The price is CA $1,226 per night from Mar 21 to Mar 22
CA $1,226
CA $1,544 total
Mar 21 - Mar 22
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (1,000 reviews)
Everything about this hotel is incredible!
Reviewed on Feb 20, 2026
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
The price is CA $905 per night from Mar 10 to Mar 11
CA $905
CA $1,163 total
Mar 10 - Mar 11
includes taxes & fees
Book a stay at this 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! (1,007 reviews)
Everything was great especially the grounds absolutely stunning. The only knock i would give it is the outside of the overall hotel needs a bit of paint or some refreshment other than that the rooms were spacious clean and the grounds were gorgeous kids loved the pool and beach very much overall ...
Reviewed on Feb 25, 2026
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,233 per night from Mar 7 to Mar 8
CA $1,233
CA $1,546 total
Mar 7 - Mar 8
includes taxes & fees
Book a stay at this 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! (1,004 reviews)
Incredible sunset views Great beach Friendly staff that were good at turning over unused sunbeds on the beach and cocktail staff at the restaurants were particularly good Resort was very clean and beautifully designed Liked the water refill in the lovely fairmont bottles Minor quibbles Limited non ...
Reviewed on Feb 21, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street Kihei HI
Fully refundableReserve now, pay when you stay
The price is CA $1,465 per night from Mar 23 to Mar 24
CA $1,465
CA $1,820 total
Mar 23 - Mar 24
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our ...
Ho‘olei Villas at Grand Wailea
146 Ho'olei Circle Kihei HI
The price is CA $2,790 per night from Mar 1 to Mar 2
CA $2,790
CA $3,401 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this 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! (44 reviews)
We stayed in Villa 99-5. . To sum it up quickly, the price to experience was in our opinion way too high. Also as a member an elite member, I did not get the discounts on the Cabana rentals and beach chair. The restaurant staff and food was very good. For the price we believe that there should be ...
Reviewed on Oct 22, 2025
Fairmont Kea Lani Maui Villa Experience
4100 Wailea Alanui Dr-Building A Kihei HI
The price is CA $4,438 per night from Feb 28 to Mar 1
CA $4,438
CA $5,349 total
Feb 28 - Mar 1
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free breakfast, free valet parking, and 3 outdoor pools. Popular attractions Wailea Beach and Polo Beach are ...
Wailea Luxury Hilltop Resort Vistas
10 Wailea Ekolu Pl Kihei HI
Book a stay at this luxury apartment in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located ...
10/10 Exceptional! (2 reviews)
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
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
Grand Wailea Maui, A Waldorf Astoria Resort
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Everything was top of tier really enjoyed my stay. "
A verified traveller stayed at Grand Wailea Maui, A Waldorf Astoria Resort
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