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Wailea Vacation Packages

Indulge in Hawai’i’s high life with a stay in this beautiful coastal area known for its luxury accommodation and secluded beaches. 

Enjoy a luxury Hawaiian experience in the sheltered community of Wailea. A vacation here will exceed even the high expectations most people have for a trip to these paradise islands. Breathtaking ocean vistas, five wonderfully tranquil beaches and a selection of excellent golf courses make this part of Hawai’i a favorite with high-end holidaymakers.

Wailea is home to several luxury resorts and hotels. One look at the immediate surroundings and it’s easy to understand why these businesses have chosen his spot to offer the ultimate in indulgence and relaxation. The beaches in this area are perfect, with Wailea Beach having once even been named “America’s Best Beach.”

Spend your time here relaxing. Spend all day at the beach sunbathing, swimming or snorkeling. Which beach you choose depends on what you’re looking for. Makena Beach is the place to go for dreamlike views of a nearly untouched stretch of sand. Or, step into the calm waters at Polo Beach to explore the rich marine life of the area, undisturbed by strong waves and currents.

While away an afternoon at Wailea Golf Club, taking advantage of a rare opportunity to play some rounds amid idyllic scenery. Afterwards, unwind with a treatment at one of the extravagant local spas or carry on your sports session at Wailea Tennis Club.

Outdoorsy people of all ages and levels of ability should definitely add Makena Stables to their itinerary. View Wailea’s stunning landscapes from the back of a horse. Some rides are organized for the evening, set against the backdrop of an impossibly perfect Hawaiian sunset.

High-end dining and shopping options abound. Treat yourself to a shopping spree at the Shops at Wailea, where classic brands such as Gucci and Louis Vuitton can be found next to more affordable chain stores. Afterwards, enjoy dinner set to live music or head down to the sand to get the perfect photo of that iconic Hawaiian sunset.

From Kahului Airport, drive south across Maui’s narrowest part to reach Wailea. Within just half an hour, you’ll be closer to heaven than you thought was possible.

Accommodation in Wailea

Wailea is a highly popular destination for travelers, and boasts a fine range of places to stay. Expedia's Wailea lodging guide has all the details.

The Ho'olei at Grand Wailea and Wailea Beach Villas, A Destination Luxury Hotel are among the most popular accommodation options to be found on the island.

Popular Activities in Wailea

Life is either a wonderful adventure or nothing at all, so why not jump into some new and exhilarating experiences?

Wailea has a range of activities on offer. Here are some suggestions to get you started:

For a comprehensive range of activities, check out the Wailea things to do page.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


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These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.