
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
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

Fairmont Kea Lani Maui
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

Wailea Beach Resort - Marriott, Maui
Very good resort with less crowds
Reviewed on 30 Mar 2026
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