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Wailea Vacations

Pack those stellar shades. We have Wailea vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Wailea – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Wailea vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Wailea

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Wailea vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Wailea well.

Wailea Flight + Hotel packages

Top Hotel Deals

See all 249 Hotels in Wailea
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei
    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 ...

    Four Seasons Resort Maui at Wailea$559

    Four Seasons Resort Maui at Wailea$559
    Wailea Beach Resort - Marriott, Maui

    Wailea Beach Resort - Marriott, Maui

    3700 Wailea Alanui Dr, Kihei
      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 ...

      Wailea Beach Resort - Marriott, Maui$351

      Wailea Beach Resort - Marriott, Maui$351
      Grand Wailea, A Waldorf Astoria Resort

      Grand Wailea, A Waldorf Astoria Resort

      3850 Wailea Alanui Drive, Kihei
        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; ...

        Grand Wailea, A Waldorf Astoria Resort$399

        Grand Wailea, A Waldorf Astoria Resort$399
        Fairmont Kea Lani Maui

        Fairmont Kea Lani Maui

        4100 Wailea Alanui Dr, Kihei
          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) ...

          Fairmont Kea Lani Maui$391

          Fairmont Kea Lani Maui$391
          Residence Inn by Marriott Maui Wailea

          Residence Inn by Marriott Maui Wailea

          75 Wailea Ike, Kihei
            3.0 out of 5.0
             
             

            Located in Wailea, this hotel is within 1 mi (2 km) of Shops at Wailea and Wailea Beach. Ulua Beach and Mokapu Beach are also within 15 minutes.

            Residence Inn by Marriott Maui Wailea$299

            Residence Inn by Marriott Maui Wailea$299
            Wailea Ekahi Village, A Destination Residence

            Wailea Ekahi Village, A Destination Residence

            3300 Wailea Alanui, Kihei
              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 ...

              Wailea Grand Champions, A Destination Residence

              Wailea Grand Champions, A Destination Residence

              155 Wailea Ike Place, Kihei
                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. ...

                Andaz Maui at Wailea Resort - a concept by Hyatt

                Andaz Maui at Wailea Resort - a concept by Hyatt

                3550 Wailea Alanui Dr, Kihei
                  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 ...

                  Andaz Maui at Wailea Resort - a concept by Hyatt$404

                  Andaz Maui at Wailea Resort - a concept by Hyatt$404
                  Hotel Wailea, Relais & Chateaux- Adults Only

                  Hotel Wailea, Relais & Chateaux- Adults Only

                  555 Kaukahi Street, Kihei
                    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 ...

                    Hotel Wailea, Relais & Chateaux- Adults Only$549

                    Hotel Wailea, Relais & Chateaux- Adults Only$549
                    Makena Surf, A Destination Residence

                    Makena Surf, A Destination Residence

                    4850 Makena Alanui, Kihei
                      4.0 out of 5.0
                       
                       

                      Located along a half-mile stretch of Pa'ipu Beach near La Perouse Bay, Makena Surf is a fantastic choice for a secluded Hawaii beachfront vacation, with 90 holes ...

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                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.