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

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is NZ$2,080 per night from 16 Dec to 17 Dec
NZ$2,080
16 Dec - 17 Dec
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 ...
"Loved everything about our stay. Staff was always so kind, food was delicious, and rooms were so clean"

Reviewed on 12 Nov 2026

Opens in a new windowFairmont Kea Lani Maui
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
3700 Wailea Alanui Dr Kihei HI
The price is NZ$1,261 per night from 10 Dec to 11 Dec
NZ$1,261
10 Dec - 11 Dec
includes taxes & fees
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. ...
"The staff was amazing. However the resort itself is not worth the price. It’s outdated and parts of the resort is going under construction so the construction crew is banging and making noise early in the morning. I’m on vacation, so I shouldn’t be awoken at 6am by the construction going on. I think ..."

Reviewed on 10 Nov 2026

Opens in a new windowWailea Beach Resort - Marriott, 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$1,595 per night from 29 Nov to 30 Nov
NZ$1,595
29 Nov - 30 Nov
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. ...
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.

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