2026 5 Star Hotels in Wailea

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Featured 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
Grand 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
Four Seasons Resort Maui at Wailea
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
3700 Wailea Alanui Dr Kihei HI
Wailea Beach Resort - Marriott, Maui
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
Fairmont Kea Lani Maui
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
555 Kaukahi Street, Maui Wailea HI
Fully refundableReserve now, pay when you stay
Hotel Wailea Maui
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
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
Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom

5 out of 5
3200 Wailea Alanui Dr Kihei HI
Villa, Garden View, 2-bedroom
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
See all 1,210 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.