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Kalaupapa Vacations

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

Hotwire can help you find your travel bliss with Kalaupapa 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 Kalaupapa

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 Kalaupapa 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 Kalaupapa well.

Top Hotel Deals

See all 1,160 Properties in Kalaupapa
The Ritz-Carlton, Kapalua

The Ritz-Carlton, Kapalua

1 Ritz Carlton Dr, Lahaina
    5.0 out of 5.0
     
     

    54 tropical oceanfront acres in the heart of Kapalua surrounded by world-class golf courses, award-winning D.T. Fleming Beach, and one of Maui’s largest nature ...

    The Ritz-Carlton, Kapalua$399

    The Ritz-Carlton, Kapalua$399
    Kaanapali Beach Club Resort by Diamond Resorts

    Kaanapali Beach Club Resort by Diamond Resorts

    104 Kaanapali Shores Pl, Lahaina
      3.5 out of 5.0
       
       

      On the beach in Maui, this all-suite resort is within easy reach of West Maui Beach, 4 miles from historic Lahaina, and within 5 miles of the championship golf ...

      Kaanapali Beach Club Resort by Diamond Resorts$279

      Kaanapali Beach Club Resort by Diamond Resorts$279
      Aston at Papakea Resort

      Aston at Papakea Resort

      3543 Lower Honoapiilani Rd, Lahaina
        3.0 out of 5.0
         
         

        Family-friendly Aston at Papakea Resort is located in West Maui's sunny and easygoing Honokowai area, adjacent to a sandy beach, 2 miles from Kaanapali golf, ...

        Aston at Papakea Resort$199

        Aston at Papakea Resort$199
        Montage Kapalua Bay

        Montage Kapalua Bay

        One Bay Drive, Lahaina
          5.0 out of 5.0
           
           

          Offering direct access to the beach, this Napili, Hawaii condo resort is within a 15-minute walk of Kapalua Golf Resort Bay Course and Kapalua Beach. D.T. Fleming ...

          Montage Kapalua Bay$955

          Montage Kapalua Bay$955
          Kahana Falls Resort

          Kahana Falls Resort

          4260 Lower Honoapiilani Rd, Lahaina
            3.5 out of 5.0
             
             

            This family-friendly Lahaina condo building is located near the beach, within 3 mi (5 km) of Kahekili Beach and Kapalua Beach. Napili Bay and Kapalua Golf Resort ...

            Polynesian Shores

            Polynesian Shores

            3975 Lower Honoapiilani Road, Lahaina
              3.0 out of 5.0
               
               

              Nestled on the beach, this Lahaina condo building is 1.4 mi (2.2 km) from Kahekili Beach and 3 mi (4.8 km) from Kaanapali Beach. Napili Bay and Black Rock are ...

              Aston Mahana at Kaanapali

              Aston Mahana at Kaanapali

              110 Ka'anapali Shores Place, Lahaina
                3.5 out of 5.0
                 
                 

                With views of the islands of Molokai and Lanai, Aston Mahana at Kaanapali hugs the shoreline north of Black Rock, where busy Kaanapali Resort begins; historic ...

                Hotel Moloka'i

                Hotel Moloka'i

                1300 Kamehameha V Hwy, Kaunakakai
                  3.0 out of 5.0
                   
                   

                  Nestled on the beach, this Kaunakakai hotel is 2.6 mi (4.2 km) from Kapuaiwa Coconut Grove and 9.2 mi (14.8 km) from Ironwood Hills Golf Club.

                  Hotel Moloka'i$132

                  Hotel Moloka'i$132
                  Napili Kai Beach Resort

                  Napili Kai Beach Resort

                  5900 Lower Honoapiilani Rd, Lahaina
                    3.5 out of 5.0
                     
                     

                    Set on 10 beachfront acres in West Maui, Napili Kai Beach Resort is adjacent to Kapalua and 12 miles north of Lahaina Town. Trade winds waft peacefully through ...

                    Napili Kai Beach Resort$335

                    Napili Kai Beach Resort$335
                    Napili Shores Maui by Outrigger

                    Napili Shores Maui by Outrigger

                    5315 Lower Honoapiilani Rd, Lahaina
                      3.0 out of 5.0
                       
                       

                      Kaanapali is home to Outrigger Napili Shores, a low-key haven set on Napili Bay in northwest Maui; an ocean-side path leads right to a sandy beach, just 50 yards ...

                      Napili Shores Maui by Outrigger$189

                      Napili Shores Maui by Outrigger$189

                      Top Flight Deals

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