Wailea Holidays, Packages & Deals 2025

Top hotels for your Wailea holiday

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

NZ$1,472

14 Sept - 15 Sept

includes taxes & fees

Stay at this 5-star 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 ...

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI

NZ$1,885

1 Oct - 2 Oct

includes taxes & fees

Stay at this 5-star luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Kihei, HI

NZ$1,587

7 Oct - 8 Oct

includes taxes & fees

Stay at this 4.5-star luxury resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

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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.

Popular places to visit

Wailea Beach

Nothing says holiday like spending a lazy day at Wailea Beach, a popular beach in Kihei. Wander the seaside or discover the beautiful sunsets in this relaxing area.

Maluaka Beach

If a restful holiday is part of your travel plans, Maluaka Beach might be the perfect place to visit during your trip to Makena. Discover the beautiful sunsets in this relaxing area or enjoy its snorkelling spots.

Makena State Park Beach

If a restful holiday is part of your travel plans, Makena State Park Beach might be the perfect place to visit during your trip to Makena. Stroll along the seaside in this relaxing area or seek out the snorkelling spots.