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Aug 21 - Aug 23
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Aug 28 - Aug 30

Featured Wailea 5 Star hotels

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,344 per night from Aug 17 to Aug 18
CA $1,344
CA $1,693 total
Aug 17 - Aug 18
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 ...
Opens in a new windowFairmont Kea Lani Maui
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 $1,015 per night from Aug 29 to Aug 30
CA $1,015
CA $1,295 total
Aug 29 - Aug 30
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 ...
8.6/10 Excellent! (1,001 reviews)
"This was a lovely stay. We ended up in the Napua wing and it truly was great. The staff was very kind and remembered our names instantly. A lazy river should come with every hotel hahaha!"

Reviewed on Aug 14, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
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 $1,145 per night from Aug 24 to Aug 25
CA $1,145
CA $1,449 total
Aug 24 - Aug 25
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 ...
Opens in a new windowFour Seasons Resort Maui at Wailea
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 $1,053 per night from Aug 31 to Sep 1
CA $1,053
CA $1,333 total
Aug 31 - Sep 1
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 ...
9.4/10 Exceptional! (1,004 reviews)
"Great atmosphere relaxing,.quiet & beautiful!"

Reviewed on Aug 16, 2026

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 $2,388 per night from Sep 5 to Sep 6
CA $2,388
CA $2,925 total
Sep 5 - Sep 6
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 Grand Wailea ...
Opens in a new windowHo‘olei Villas at Grand Wailea
NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts

NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts

5 out of 5
3200 Wailea Alanui Dr Kihei HI
Book a stay at this luxury condo in Kihei. Enjoy free parking, a beach locale, and free grocery shopping service. Popular attractions Wailea Beach and Keawakapu ...
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Opens in a new windowNEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts
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 $4,064 per night from Aug 26 to Aug 27
CA $4,064
CA $4,922 total
Aug 26 - Aug 27
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 ...
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
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! (3 reviews)
"The best place while we in Hawaii. The first time we had a place with cool Ac . Nice view . Gotta to stay here guys. Big kitchen and clean everywhere. Awesome bathroom, the mirror with light and the view from kitchen.. Amazing❤️"

Reviewed on Aug 11, 2026

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Opens in a new windowWailea Luxury Hilltop Resort Vistas
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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.

Recent Wailea hotel reviews by fellow wanderers

Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Everything was very good. I only wished there were more variety with the breakfast."
A verified traveller stayed at Residence Inn by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea

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