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Apr 20 - Apr 21
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Apr 21 - Apr 22
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Apr 24 - Apr 26
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May 1 - May 3

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 $1,088 per night from Apr 21 to Apr 22
CA $1,088
CA $1,292 total
Apr 21 - Apr 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! (1,007 reviews)
Everything about the hotel and staff is exceptional - there is no better place to stay!

Reviewed on Apr 20, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,436 per night from Apr 21 to Apr 22
CA $1,436
CA $1,786 total
Apr 21 - Apr 22
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! (1,002 reviews)
Incredibly good service and staff. Property very clean. Very attentive.

Reviewed on Apr 18, 2026

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 $905 per night from May 3 to May 4
CA $905
CA $1,163 total
May 3 - May 4
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! (1,003 reviews)
No response from front desk when the water was turned off.

Reviewed on Apr 17, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
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 $1,059 per night from May 10 to May 11
CA $1,059
CA $1,338 total
May 10 - May 11
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! (1,001 reviews)
Everything was Amazing!! Will be coming back

Reviewed on Apr 18, 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 $2,712 per night from May 9 to May 10
CA $2,712
CA $3,309 total
May 9 - May 10
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! (46 reviews)
This was a beautiful villa across the street from the grand wailea. Booking included full use of the resort, which was excellent. Included was a shuttle service with uber-like app that we could use to go anywhere within a 1 mile radius. This was a great stay

Reviewed on Apr 19, 2026

Opens in a new windowHo‘olei Villas at Grand Wailea
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! (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

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Opens in a new windowWailea Luxury Hilltop Resort Vistas
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 $4,804 per night from May 9 to May 10
CA $4,804
CA $5,784 total
May 9 - May 10
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
Grand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units, 3 Bedrooms Ml-1499

Grand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units, 3 Bedrooms Ml-1499

5 out of 5
155 Wailea Ike Pl Kihei HI
Book a stay at this luxury condo in Kihei. Enjoy free parking, private hot tubs, and free grocery shopping service. Popular attractions Wailea Beach and Shops ...
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Opens in a new windowGrand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units, 3 Bedrooms Ml-1499
Wailea Elua Collection by KBM - 2 Units (2009/2103)

Wailea Elua Collection by KBM - 2 Units (2009/2103)

5 out of 5
3600 Wailea Alanui Drive Kihei HI
Book a stay at this luxury condo in Kihei. Enjoy a beach locale, private hot tubs, and free grocery shopping service. Popular attractions Wailea Beach and Wailea ...
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Opens in a new windowWailea Elua Collection by KBM - 2 Units (2009/2103)
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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

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Everything about the hotel and staff is exceptional - there is no better place to stay! "
A verified traveller stayed at Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea

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