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Wailea Vacation Packages

Trying to save time and money on your next vacation to Wailea? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Wailea trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. AARP Travel Center has an amazing selection of flights and hotels, as well as Wailea endeavors to pick from.

Wailea Hotel Deals

You can choose from around 851 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Wailea hot spots, we have plenty of options available.

We have competitive rates on everything from all-inclusive resorts that check off all the vacation must-haves to affordable hotels perfect for those on a budget. You can scan all the options and pick the lodging that is ideal for you. With AARP Travel Center's Wailea hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.

Things to do in Wailea

Wailea is the perfect town when you have to a break from it all. With only around 99 people in the area, this quaint town is just right for a quite vacation.

The AARP Travel Center "Things to Do" page has more great activities that you can book.

Book Together and Save

As an AARP Member, you get to benefit from all the great savings. You'll save on select hotels worldwide, flights, and even car rentals. No matter what Wailea vacation package you select, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Bundle today and get ready for your Wailea vacation.

Top Hotel Deals

See all 851 Properties in Wailea

Estimated price for 1 night/2 adults

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI
    4.5 out of 5.0
     
     

    Located in Wailea, this beachfront resort is next to a golf course and within 2 mi (3 km) of Shops at Wailea, Wailea Beach, and Keawakapu Beach. Kamaole Beach ...

    Wailea Beach Resort - Marriott, Maui

    Wailea Beach Resort - Marriott, Maui

    3700 Wailea Alanui Dr, Kihei, HI
      4.5 out of 5.0
       
       

      This family-friendly Kihei resort is located on the waterfront, within 1 mi (2 km) of Shops at Wailea and Keawakapu Beach. Wailea Beach and Kamaole Beach Park ...

      Four Seasons Resort Maui at Wailea

      Four Seasons Resort Maui at Wailea

      3900 Wailea Alanui Drive, Kihei, HI
        5.0 out of 5.0
         
         

        Located in Wailea, this beachfront resort is next to a golf course and within 3 mi (5 km) of Wailea Blue Golf Course, Wailea Beach, and Keawakapu Beach. Kamaole ...

        Andaz Maui at Wailea Resort - a concept by Hyatt

        Andaz Maui at Wailea Resort - a concept by Hyatt

        3550 Wailea Alanui Dr, Kihei, HI
          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 Shops at Wailea and Keawakapu Beach. Wailea Beach and Kamaole Beach ...

          Fairmont Kea Lani Maui

          Fairmont Kea Lani Maui

          4100 Wailea Alanui Dr, Kihei, HI
            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 Wailea Blue Golf Course and Wailea Beach. Keawakapu Beach is 2.2 ...

            Residence Inn by Marriott Maui Wailea

            Residence Inn by Marriott Maui Wailea

            75 Wailea Ike, Kihei, HI
              3.5 out of 5.0
               
               

              Located in Wailea, this hotel is 0.2 mi (0.4 km) from Shops at Wailea and within 3 mi (5 km) of Wailea Beach and Keawakapu Beach. Kamaole Beach Park 3 is 2.5 ...

              Palms at Wailea Maui by Outrigger

              Palms at Wailea Maui by Outrigger

              3200 Wailea Alanui Dr, Kihei, HI
                3.5 out of 5.0
                 
                 

                Located in Wailea, this golf condo resort is within 1 mi (2 km) of Mokapu Beach and Keawakapu Beach. Wailea Beach and Kamaole Beach Park 3 are also within 2 ...

                Hotel Wailea, Relais & Chateaux- Adults Only

                Hotel Wailea, Relais & Chateaux- Adults Only

                555 Kaukahi Street, Kihei, HI
                  5.0 out of 5.0
                   
                   

                  Located in Wailea, this luxury resort is 0.5 mi (0.7 km) from Wailea Blue Golf Course and within 3 mi (5 km) of Wailea Beach and Keawakapu Beach. Polo Beach ...

                  Wailea Ekahi Village, A Destination Residence

                  Wailea Ekahi Village, A Destination Residence

                  3300 Wailea Alanui, Check-in: 34 Wailea Gateway Pl. A102, Kihei, HI
                    3.0 out of 5.0
                     
                     

                    Located in Wailea, this beachfront condo building is next to a golf course and within a 15-minute walk of Shops at Wailea and Keawakapu Beach. Wailea Beach and ...

                    Wailea Beach Villas, A Destination Luxury Hotel

                    Wailea Beach Villas, A Destination Luxury Hotel

                    3800 Wailea Alanui Drive, Kihei, HI
                      4.5 out of 5.0
                       
                       

                      Located in Wailea, this beachfront condo resort is next to a golf course and within a 15-minute walk of Shops at Wailea, Ulua Beach, and Ulua Beach Park. Mokapu ...

                      Top Flight Deals

                      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.