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Kaupo Vacations

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

Hotwire can help you find your travel bliss with Kaupo 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 Kaupo

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 Kaupo 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 Kaupo well.

Kaupo Flight + Hotel packages

Top Hotel Deals

See all 35 Hotels in Kaupo
Travaasa Hana, Maui

Travaasa Hana, Maui

5031 Hana Hwy, Hana
    4.0 out of 5.0
     
     

    Set amid the picturesque oceanfront community of "Heavenly Hana" on Maui's secluded eastern shore, this resort is close to Hamoa Beach.

    Travaasa Hana, Maui$525

    Travaasa Hana, Maui$525
    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
      Hana Kai Maui

      Hana Kai Maui

      4865 Uakea Rd, Hana
        3.0 out of 5.0
         
         

        Located in Hana, this beachfront condo building is in the historical district, 2.6 mi (4.2 km) from Hamoa Beach, and 4.7 mi (7.6 km) from Kahanu Garden.

        Wailea Ekolu Village, A Destination Residence

        Wailea Ekolu Village, A Destination Residence

        10 Wailea Ekolu Place, Kihei
          3.5 out of 5.0
           
           

          Located in Wailea, this golf condo building is 0.6 mi (0.9 km) from Shops at Wailea and 1.7 mi (2.8 km) from Wailea Beach. Ulua Beach and Mokapu Beach are also ...

          Kailani Suite at Hana Kai Resort

          Kailani Suite at Hana Kai Resort

          4865 Uakea Rd, Hana
            2.5 out of 5.0
             
             

            Situated near the beach, this condo building is 0.5 mi (0.8 km) from Red Sand Beach and 3 mi (4.9 km) from Wainapanapa State Park. Fagan Memorial and Hamoa Beach ...

            Kailani Suite at Hana Kai Resort$275

            Kailani Suite at Hana Kai Resort$275
            Hale Kiana

            Hale Kiana

            112 Mano Dr, Kula
              3.0 out of 5.0
               
               

              Situated by the ocean, this apartment building is within 16 mi (25 km) of Alexander and Baldwin Sugar Museum, Haleakala National Park, and H.A. Baldwin Beach ...

              Wailea Ekolu

              Wailea Ekolu

              10 Wailea Ekolu Place, Kihei
                3.5 out of 5.0
                 
                 

                Located in Wailea, this condo building is 0.6 mi (0.9 km) from Shops at Wailea and 1.3 mi (2.1 km) from Wailea Beach. Ulua Beach and Mokapu Beach are also within ...

                Top Flight Deals

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