Wailea Holiday Deals

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Top hotels for your Wailea holiday

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
The price is NZ$1,617 per night from 4 Jan to 5 Jan
NZ$1,617
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
This property has long been one of my global Four Seasons favorites, and I remain truly grateful for the warm hospitality I always receive. I was also very appreciative of the wonderful upgrade to an ocean-view room — mahalo for that thoughtful gesture. I’ve been visiting this resort regularly since ...

Reviewed on 2 Dec 2025

Opens in a new windowFour Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is NZ$1,846 per night from 8 Jan to 9 Jan
NZ$1,846
8 Jan - 9 Jan 2026
includes taxes & fees
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 ...
Room setup was great, pools and beach were excellent. Everyone had a great time

Reviewed on 22 Dec 2025

Opens in a new windowFairmont 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
The price is NZ$1,504 per night from 10 Jan to 11 Jan
NZ$1,504
10 Jan - 11 Jan 2026
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy free Wi-Fi, 9 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
Very nice resort for a family vacation!

Reviewed on 23 Dec 2025

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
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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 showing a sandy beach, tropical scenes and swimming

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.

Wailea Beach
Maluaka Beach which includes rocky coastline, mountains and a pebble beach

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.

Maluaka Beach
Makena Beach State Park showing a beach

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 romantic area or seek out the snorkelling spots.

Makena State Park Beach