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Kaupakulua Vacations

Pack those stellar shades. We have Kaupakulua 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 Kaupakulua – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Kaupakulua 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 Kaupakulua

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 Kaupakulua 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 Kaupakulua well.

Kaupakulua Flight + Hotel packages

Top Hotel Deals

See all 1,458 Properties in Kaupakulua
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave, Kahului
    2.5 out of 5.0
     
     

    Across from Kaahumanu Center, the hotel is within 3 miles of the airport, downtown Kahului, and Wailuku, and within 7 miles of Kihei beaches. The hotel is also ...

    Maui Seaside Hotel$154

    Maui Seaside Hotel$154
    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; ...

      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$599

        Four Seasons Resort Maui at Wailea$599
        Maui Coast Hotel

        Maui Coast Hotel

        2259 S Kihei Rd, Kihei
          3.5 out of 5.0
           
           

          Surrounded by shops and restaurants, this seven-story hotel is across the street from Kamaole Beach Park I, 3 miles from upscale Wailea, and 7 miles from Maui ...

          Maui Coast Hotel$250

          Maui Coast Hotel$250
          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
            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$492

              Fairmont Kea Lani Maui$492
              Maui Beach Hotel

              Maui Beach Hotel

              170 Kaahumanu Avenue, Kahului
                2.5 out of 5.0
                 
                 

                Tikis dot the lawn of this Maui hotel, right on the harbor in Kahului, Hawaii, 2 miles from Kahana Beach Park, and 5 miles from Iao Valley State Park. Kahului ...

                Maui Beach Hotel$129

                Maui Beach Hotel$129
                Days Inn by Wyndham Maui Oceanfront

                Days Inn by Wyndham Maui Oceanfront

                2980 S Kihei Road, Kihei
                  2.5 out of 5.0
                   
                   

                  Set on a splendid stretch of sand 2 miles from Kihei, this low-rise hotel is 3 miles from the championship golf courses of Wailea Resort; Maui Ocean Center is ...

                  Days Inn by Wyndham Maui Oceanfront$132

                  Days Inn by Wyndham Maui Oceanfront$132
                  Courtyard Maui Kahului Airport

                  Courtyard Maui Kahului Airport

                  532 Keolani Place, Kahului
                    3.5 out of 5.0
                     
                     

                    Situated near the airport, this hotel is within 3 mi (5 km) of Kanaha Beach Park, Maui Arts and Cultural Center, and Maui Nui Botanical Gardens. Queen Ka’ahumanu ...

                    Courtyard Maui Kahului Airport$259

                    Courtyard Maui Kahului Airport$259
                    Luana Kai Resort

                    Luana Kai Resort

                    940 S. Kihei Road, Kihei
                      3.0 out of 5.0
                       
                       

                      Offering direct access to the beach, this Kihei condo building is within a 10-minute walk of Waipuilani Park and Kalepolepo. Maui Nui Golf Club and Kihei Regional ...

                      Top Flight Deals

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