Wailea Holiday Packages

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Holidays To Wailea

Life’s a beach…at least, you want it to be. Well, in Wailea, Hawaii, life includes several beaches, plus delicious island cuisine and dolphin-watching, too!

Catch the next wave to the west coast of Maui to start your dream holiday in Wailea. By day you can be a beachcombing connoisseur after dark, sample the local concerts and festivals. Oh, and did we mention that Wailea takes spa days very seriously? Well, you’ve gotta wind down from all that surfing, golfing and sunbathing you’ll be doing.

Already packing your bathers and sunnies? Book one of Wotif’s Wailea packages and head to the Pacific!

Things to Do in Wailea

Wailea holidays are just one beautiful snapshot after another, with more beaches than many big coastal cities, so pick up one of Wotif’s Wailea car rental deals and start cruising. Wailea Beach is a good place to start and not just because the name is easy to remember—it also happens to be beautiful and uncrowded. From there, you’ll be close to the Coastal Nature Trail, which is perfect for runners, cyclists and bird-watchers.

Golf enthusiasts—or beach enthusiasts who like riding the golf carts—can work on their back swing at waterfront golf courses. Just don’t drive the ball right into the Pacific Ocean.

To make some fine finned friends, drive south of Wailea to La Perouse Bay, where you can get up close and personal with dolphins at the end of the historic King’s Trail. Yes, dolphins, right in front of you!

Shopping, Dining & Nightlife

When it comes to bringing home a big haul, Wailea doesn’t mess around. For the full luxury mall experience with dining and entertainment, too, spend the arvo at The Shops at Wailea. In Kihei, Wailea’s neighbour to the north, check out the Kihei Kalama Village Marketplace for an open-air experience and local treasures.

Even in a village in Maui, you can take care of your cravings for Italian cuisine, because the Wailea waterfront is lined with global dining as well as delicious dishes you won’t find anywhere else. Dig into the fresh seafood and fish you’ll think for sure swam right up to the kitchen. The local poke and mahi mahi are a must, and nothing says “Aloha” to your taste buds like a mai tai—one of Hawaii’s signature cocktails.

Speaking of cocktails, Wailea has a top-notch bar scene, with live music filling the streets every night. Catch a concert or make your way out to the beach for a traditional luau to learn how to sway the island way. Wailea is known throughout Hawaii for its nightly luaus. You don’t want to end your Wailea holiday without joining the party!

What’s Next?

Ready to catch the next wave—er, we mean flight? Mix and match awesome Hawaii packages with Wotif to save on flights and accommodation all over the “Aloha State”. Start browsing holiday packages in Wailea and you’ll be island-hopping before you know it!

Top Wailea hotels

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$1,401 per night from 3 May to 4 May
NZ$1,401
includes taxes & fees
3 May - 4 May
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition ...
"One of the best resorts in Hawaii"

Reviewed on 26 Apr. 2025

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is NZ$1,925 per night from 8 May to 9 May
NZ$1,925
includes taxes & fees
8 May - 9 May
Stay at this 4.5-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 ...
"NA"

Reviewed on 25 Apr. 2025

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
The price is NZ$1,779 per night from 3 May to 4 May
NZ$1,779
includes taxes & fees
3 May - 4 May
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 ...
"Very nice stay-grounds are beautiful. Staff at adult only pool 7/10-ran into many staff being short in their language to enforce wrist bands. For the price of resort it would be nice to have better customer service. Rest of staff very helpful and kind."

Reviewed on 23 Apr. 2025

Grand 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.