Wailea Holidays, Packages & Deals 2026

Top hotels for your Wailea holiday

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

Stay at this luxury resort in Kihei. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...

Last night on an extended trip to Asia, stopped over in Maui. A perfect end to our trip (despite the inclement weather). We have always stayed in the Ka'anapali area of Maui, but due to weather Wailea was better option for this trip and The Four Seasons didn't disappoint. Would definitely consider ...

Reviewed on 28 Mar 2026

Get rates

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

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 condition ...

Staff was incredibly welcoming and helpful. Bar/restaurant staff were amazing. Pools were clean and poolside servers were very friendly. Overall an amazing property with wonderful staff

Reviewed on 16 Mar 2026

Get rates

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI

Stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa and 4 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...

Great memories

Reviewed on 28 Mar 2026

Get rates

Don't see what you're looking for?

See all available properties in Wailea

View all properties

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 romantic 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 Kihei. 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 Kihei. Stroll along the seaside in this relaxing area or seek out the snorkelling spots.