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 $1,058 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

Grand Wailea Maui, A Waldorf Astoria Resort
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

Fairmont Kea Lani Maui
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

Hotel Wailea, Relais & Chateaux - Adults Only
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

Ho‘olei Villas at Grand Wailea
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

Fairmont Kea Lani Maui Villa Experience
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

Wailea Luxury Hilltop Resort Vistas
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
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

Fairmont Kea Lani Maui
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"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 up every morning. Housekeeping was impeccable, the food was delicious and having a semi-private beach with chairs and umbrellas was amazing to sit and relax the day away. We also enjoyed the spa while we were there and the services we received were so relaxing, a perfect way to end our perfect honeymoon. We would definitely recomment the Fairmont Kea Lani and can't wait to come back again."
A verified traveller stayed at Fairmont Kea Lani Maui
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