Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


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.


Top Hotel Deals

See all 248 Hotels in Wailea
Andaz Maui at Wailea Resort - a concept by Hyatt $404
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Kihei
     
    4.6
    of 5, from 594 reviews
    4.5 out of 5.0

    Located in Wailea, this beachfront resort is next to a golf course and within 1 mi (2 km) of Ulua Beach and Wailea Beach. Mokapu Beach and Ulua Beach Park are also within 10 minutes.

    Hotel Wailea, Relais & Chateaux- Adults Only $549
    Hotel Wailea, Relais & Chateaux- Adults Only

    Hotel Wailea, Relais & Chateaux- Adults Only

    555 Kaukahi Street, Kihei
       
      4.5
      of 5, from 665 reviews
      5.0 out of 5.0

      Situated near the beach in Wailea, this spa resort is close to Wailea Blue Golf Course, Wailea Beach, and Wailea Emerald Golf Course. Also nearby are Wailea Gold Golf Course and Polo Beach.

      Grand Wailea, A Waldorf Astoria Resort $409
      Grand Wailea, A Waldorf Astoria Resort

      Grand Wailea, A Waldorf Astoria Resort

      3850 Wailea Alanui Drive, Kihei
         
        4.4
        of 5, from 1,314 reviews
        4.5 out of 5.0

        Set amid waterfall gardens and a meandering canyon of pools, this grand island resort is within a mile of championship golf, a tennis center, and upscale shops; Kihei Town is three miles away.

        Wailea Grand Champions, A Destination Residence
        Wailea Grand Champions, A Destination Residence

        Wailea Grand Champions, A Destination Residence

        155 Wailea Ike Place, Kihei
           
          4.4
          of 5, from 514 reviews
          3.0 out of 5.0

          Located in Wailea, Maui, this condo resort is right on the Wailea Golf Club course. It is 1 mile from Mokapu Beach and Ulua Beach, and 1 mile from Wailea Beach. Polo Beach is 2 miles away.

          Four Seasons Resort Maui at Wailea $559
          Four Seasons Resort Maui at Wailea

          Four Seasons Resort Maui at Wailea

          3900 Wailea Alanui Drive, Kihei
             
            4.8
            of 5, from 855 reviews
            5.0 out of 5.0

            Located on Maui's sunny south shore, this resort faces the wide, crescent curve of Wailea Beach, with its sugar sands and calm waters. The Wailea Blue golf course and The Shops at Wailea are within a half-mile.

            Wailea Ekahi Village, A Destination Residence
            Wailea Ekahi Village, A Destination Residence

            Wailea Ekahi Village, A Destination Residence

            3300 Wailea Alanui, Kihei
               
              4.5
              of 5, from 273 reviews
              3.0 out of 5.0

              Located in Wailea, this beachfront condo building is next to a golf course and within 1 mi (2 km) of Ulua Beach and Wailea Beach. Mokapu Beach and Ulua Beach Park are also within 10 minutes.

              Fairmont Kea Lani Maui $367
              Fairmont Kea Lani Maui

              Fairmont Kea Lani Maui

              4100 Wailea Alanui Dr, Kihei
                 
                4.7
                of 5, from 1,291 reviews
                4.5 out of 5.0

                Set amid waterfall gardens, pools, and Polo Beach, this 22-acre oceanfront resort borders Wailea's 3 championship golf courses and is 1 mile (1.6 kilometers) from the upscale Shops at Wailea and 3 miles (4.8 kilometers) from Kihei Town.

                Wailea Beach Resort - Marriott, Maui $336
                Wailea Beach Resort - Marriott, Maui

                Wailea Beach Resort - Marriott, Maui

                3700 Wailea Alanui Dr, Kihei
                   
                  4.5
                  of 5, from 143 reviews
                  4.5 out of 5.0

                  Cradled against an oceanfront hillside, this expansive, low-rise Maui hotel lies a minute's walk from beaches and a quarter-mile from the Shops at Wailea; 3 golf courses are within 2 miles.

                  Top Flight + Hotel Deals

                  Top Deals on Flights

                  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.