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Key West Vacations

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

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

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 Key West 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 Key West well.

Key West Flight + Hotel packages

Top Hotel Deals

See all 418 Hotels in Key West
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$265

    Southernmost Beach Resort$265
    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 ...

      24 North Hotel Key West

      24 North Hotel Key West

      3820 North Roosevelt Boulevard, Key West
        4.0 out of 5.0
         
         

        Situated near the airport, this hotel is 2.2 mi (3.6 km) from Key West Harbour and within 6 mi (10 km) of Key West Lighthouse and Keeper's Quarters Museum and ...

        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$169

          Oceans Edge Key West Resort, Hotel & Marina$169
          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, ...

            Fairfield Inn & Suites by Marriott Key West, Keys Collection

            Fairfield Inn & Suites by Marriott Key West, Keys Collection

            3852 North Roosevelt Boulevard, Key West
              3.0 out of 5.0
               
               

              Located in the heart of Key West, this hotel is 1.1 mi (1.8 km) from Key West Golf Club and within 3 mi (5 km) of Key West Art and Historical Society and Smathers ...

              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$178

                The Gates Hotel Key West$178
                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 ...

                  DoubleTree Resort by Hilton Grand Key - Key West

                  DoubleTree Resort by Hilton Grand Key - Key West

                  3990 S Roosevelt Blvd, Key West
                    3.5 out of 5.0
                     
                     

                    Located on the quieter side of Key West, this tropical-style resort offers complimentary scheduled shuttle service to Duval Street as well as shuttle service ...

                    DoubleTree Resort by Hilton Grand Key - Key West$149

                    DoubleTree Resort by Hilton Grand Key - Key West$149
                    Hilton Garden Inn Key West,The Keys Collection

                    Hilton Garden Inn Key West,The Keys Collection

                    3850 N Roosevelt Blvd, Key West
                      3.5 out of 5.0
                       
                       

                      Located in the heart of Key West, this hotel is 1.1 mi (1.7 km) from Key West Golf Club and within 3 mi (5 km) of Key West Art and Historical Society and Smathers ...

                      Top Flight Deals

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