Wailea Holiday Packages

Save when you book Wailea package deals

Choose two or more items and save on your trip:

Top Wailea holiday packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kaanapali Beach Resort
Aston Mahana at Kaanapali
Wailea Beach Resort - Marriott, Maui
Aston Maui Hill
Aston at The Whaler on Kaanapali Beach
Molokini which includes colourful reefs and marine life

Book your Wailea holiday

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 AU$1,760 per night from 8 Jun to 9 Jun
AU$1,760
per night
8 Jun - 9 Jun
Four Seasons Resort Maui at Wailea: Family-friendly resort with free WiFi and 3 outdoor pools. Located on the beach.
"The most amazing four seasons. Everything here is done right."

Reviewed on 2 Jun. 2024

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 AU$1,517 per night from 18 Jun to 19 Jun
AU$1,517
per night
18 Jun - 19 Jun
Fairmont Kea Lani Maui: Family-friendly resort with free Internet and 3 outdoor pools. Located near the boardwalk.
"It’s a really nice hotel in a great location."

Reviewed on 6 Jun. 2024

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 AU$1,457 per night from 13 Jun to 14 Jun
AU$1,457
per night
13 Jun - 14 Jun
Grand Wailea Maui, A Waldorf Astoria Resort: Pet-friendly resort with free WiFi and 9 outdoor pools. Located on the beach.
"👍"

Reviewed on 4 Jun. 2024

Grand Wailea Maui, A Waldorf Astoria Resort
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.