Explore top 2025 5 Star Hotels in Wailea

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Top Wailea 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
$751 nightly
The price is $886 total per night from Sep 9 to Sep 10
$886 total
Sep 9 - Sep 10
Total with taxes and fees
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with sun loungers ...
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
$891 nightly
The price is $1,051 total per night from Sep 26 to Sep 27
$1,051 total
Sep 26 - Sep 27
Total with taxes and fees
A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's ...
Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
$755 nightly
The price is $891 total per night from Oct 2 to Oct 3
$891 total
Oct 2 - Oct 3
Total with taxes and fees
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and ...
Four 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
$942 nightly
The price is $1,111 total per night from Sep 14 to Sep 15
$1,111 total
Sep 14 - Sep 15
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet ...
Hotel 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
$2,079 nightly
The price is $2,452 total per night from Sep 17 to Sep 18
$2,452 total
Sep 17 - Sep 18
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, ...
Ho‘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
$2,063 nightly
The price is $2,434 total per night from Sep 7 to Sep 8
$2,434 total
Sep 7 - Sep 8
Total with taxes and fees
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with beach cabanas ...
Fairmont 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
This apartment features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.
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Wailea 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.

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