2026 5 Star Hotels in Wailea

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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
Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
Fairmont 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
Grand 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
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
Ho‘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
Wailea 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
Fairmont 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
Grand 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
Wailea Elua Collection by KBM - 2 Units (2009/2103)
See all 1,243 properties in Wailea
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.