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Sugarloaf Key Vacations

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

Hotwire can help you find your travel bliss with Sugarloaf Key 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 Sugarloaf Key

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 Sugarloaf Key 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 Sugarloaf Key well.

Sugarloaf Key Flight + Hotel packages

Top Hotel Deals

See all 447 Hotels in Sugarloaf Key
Sugar Loaf Lodge

Sugar Loaf Lodge

17001 Overseas Hwy, Sugarloaf Key
    2.5 out of 5.0
     
     

    Situated on the waterfront, this hotel is within 16 mi (25 km) of Key West Golf Club, Key West Art and Historical Society, and Key West Harbour. Robbie's and ...

    Pelico Paradise

    Pelico Paradise

    19068 Pelico Rd, Sugarloaf Key
      3.5 out of 5.0
       
       

      Situated in Sugarloaf Key, this vacation home is within 20 mi (32 km) of Key West Golf Club, Ernest Hemingway Home and Museum, and Key West Art and Historical ...

      Havana Cabana at Key West

      Havana Cabana at Key West

      3420 N. Roosevelt Blvd, Key West
        3.5 out of 5.0
         
         

        Situated in Key West, this hotel is close to Key West Golf Club, Key West Art and Historical Society, and Smathers Beach. Also nearby are Fort East Martello ...

        Havana Cabana at Key West$135

        Havana Cabana at Key West$135
        The Perry Hotel Key West

        The Perry Hotel Key West

        7001 Shrimp Road, Key West
          4.0 out of 5.0
           
           

          Situated on the waterfront, this resort is 1.3 mi (2.2 km) from Key West Harbour and 1.8 mi (2.8 km) from Key West Golf Club. Smathers Beach and Ernest Hemingway ...

          The Perry Hotel Key West$157

          The Perry Hotel Key West$157
          Ibis Bay Beach Resort

          Ibis Bay Beach Resort

          3101 N. Roosevelt Blvd, Key West
            2.5 out of 5.0
             
             

            The white-sand beach of Ibis Bay Beach Resort is a 5-minute drive from downtown Key West. Both the Ernest Hemingway Home & Museum and Southernmost Point are ...

            Ibis Bay Beach Resort$138

            Ibis Bay Beach Resort$138
            Southernmost Beach Resort

            Southernmost Beach Resort

            1319 Duval Street, Key West
              4.0 out of 5.0
               
               

              This Key West historical district hotel is 2 blocks from Southernmost Point. Ernest Hemingway Home and Museum, and Key West Lighthouse and Keeper's Quarters ...

              Southernmost Beach Resort$209

              Southernmost Beach Resort$209
              Oceans Edge Key West Resort, Hotel & Marina

              Oceans Edge Key West Resort, Hotel & Marina

              5950 Peninsular Avenue, Key West
                4.0 out of 5.0
                 
                 

                Situated on the boardwalk, this hotel is 0.2 mi (0.4 km) from Key West Harbour and within 3 mi (5 km) of Robbie's and Key West Golf Club. Ernest Hemingway Home ...

                Oceans Edge Key West Resort, Hotel & Marina$139

                Oceans Edge Key West Resort, Hotel & Marina$139
                The Gates Hotel Key West

                The Gates Hotel Key West

                3824 N Roosevelt Blvd, Key West
                  4.0 out of 5.0
                   
                   

                  Situated at the northern tip of Key West, this hotel is within 2 miles (3.2 kilometers) of Smathers Beach and the airport and is minutes away from Earnest Hemingway ...

                  The Gates Hotel Key West$135

                  The Gates Hotel Key West$135
                  Best Western Key Ambassador Resort Inn

                  Best Western Key Ambassador Resort Inn

                  3755 S Roosevelt Blvd, Key West
                    2.5 out of 5.0
                     
                     

                    Located on the Atlantic side of Island and just minutes from the Key West Art Society and Historical Downtown. Nearby points of interest include Smathers Beach, ...

                    Best Western Key Ambassador Resort Inn$170

                    Best Western Key Ambassador Resort Inn$170
                    Heron House - Adult Only

                    Heron House - Adult Only

                    512 Simonton St, Key West
                      3.5 out of 5.0
                       
                       

                      Heron House is surrounded by the 187 historic buildings of old Key West, and a 10-minute walk from the Ernest Hemingway Home and Museum and the waterfront at ...

                      Top Flight Deals

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