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Stock Island Vacations

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

Hotwire can help you find your travel bliss with Stock Island 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 Stock Island

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 Stock Island 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 Stock Island well.

Top Hotel Deals

See all 434 Hotels in Stock Island
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$168

    The Perry Hotel Key West$168
    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
      Key West Harbour Oceanfront Suites

      Key West Harbour Oceanfront Suites

      6000 Peninsular Ave., Key West
        3.5 out of 5.0
         
         

        Offering direct access to the beach, this Key West condo building is within 3 mi (5 km) of Key West Harbour, Robbie's, and Key West Golf Club. Smathers Beach ...

        Hemingway Hideaway

        Hemingway Hideaway

        7 Coral Way, Key West
          3.5 out of 5.0
           
           

          Situated in Key West, this vacation home is 1.1 mi (1.8 km) from Key West Harbour and 2.5 mi (4.1 km) from Key West Art and Historical Society. Robbie's and ...

          Key West Yacht Life

          Key West Yacht Life

          Key West Harbour Yacht Club Stock Island, Key West
            4.0 out of 5.0
             
             

            Nestled on the beach, this Key West houseboat is within 3 mi (5 km) of Key West Harbour, Robbie's, and Key West Golf Club. Smathers Beach and Simonton Beach ...

            Blue Sky Charter Company LLC.

            Blue Sky Charter Company LLC.

            Various Addresses, Key West
              3.0 out of 5.0
               
               

              These houseboat accommodations are located throughout the area in Key West.

              Sail Florida Adventures

              Sail Florida Adventures

              617 Front Street, Key West
                2.0 out of 5.0
                 
                 

                Nestled on the beach, this Key West houseboat is within 3 mi (5 km) of Key West Harbour, Robbie's, and Key West Golf Club. Smathers Beach and Higgs Beach are ...

                Golf Club Getaway Apartment 2

                Golf Club Getaway Apartment 2

                175 Golf Club Dr, Key West
                  3.0 out of 5.0
                   
                   

                  Situated in Key West, this vacation home is close to Key West Golf Club, Robbie's, and Key West Harbour. Local attractions also include Key West Art and Historical ...

                  Sunset Marina View Apartment 2

                  Sunset Marina View Apartment 2

                  5601 College Rd, Key West
                    3.5 out of 5.0
                     
                     

                    Situated in Key West, this condo building is close to Key West Golf Club, Key West Art and Historical Society, and Robbie's. Local attractions also include Smathers ...

                    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$144

                      Havana Cabana at Key West$144

                      Top Flight Deals

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