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Winter Haven Vacations

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

Hotwire can help you find your travel bliss with Winter Haven 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 Winter Haven

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 Winter Haven 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 Winter Haven well.

Top Hotel Deals

See all 4,490 Hotels in Winter Haven
Winter Haven Gardens Inn and Banquet Center

Winter Haven Gardens Inn and Banquet Center

1150 3rd Street SW, Winter Haven
    2.5 out of 5.0
     
     

    Situated in Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Legoland Florida and Willowbrook Golf Course ...

    Winter Haven Gardens Inn and Banquet Center$53

    Winter Haven Gardens Inn and Banquet Center$53
    Shergill Grand Hotel

    Shergill Grand Hotel

    5665 Cypress Gardens Boulevard, Winter Haven
      3.0 out of 5.0
       
       

      Situated in Winter Haven, this hotel is 0.4 mi (0.6 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. ...

      Shergill Grand Hotel$55

      Shergill Grand Hotel$55
      Howard Johnson by Wyndham Winter Haven FL

      Howard Johnson by Wyndham Winter Haven FL

      1300 3rd St Sw, Winter Haven
        1.5 out of 5.0
         
         

        Situated in Winter Haven, this motel is within a 15-minute walk of Indigo's Family Fun Center and Chain of Lakes Park. Legoland Florida and Willowbrook Golf ...

        Howard Johnson by Wyndham Winter Haven FL$72

        Howard Johnson by Wyndham Winter Haven FL$72
        Holiday Inn Winter Haven

        Holiday Inn Winter Haven

        200 Cypress Gardens Boulevard, Winter Haven
          3.0 out of 5.0
           
           

          Located in the heart of Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Legoland Florida is 3 mi (4.8 km) ...

          Holiday Inn Winter Haven$115

          Holiday Inn Winter Haven$115
          Budget Inn Winter Haven

          Budget Inn Winter Haven

          401 6th Street HWY 17N, Winter Haven
            2.0 out of 5.0
             
             

            Situated in Winter Haven, this motel is 1.2 mi (1.9 km) from Indigo's Family Fun Center and 2 mi (3.2 km) from Chain of Lakes Park. Legoland Florida and Willowbrook ...

            Lake Roy Beach Inn

            Lake Roy Beach Inn

            1823 Cypress Gardens Blvd, Winter Haven
              2.0 out of 5.0
               
               

              Located in the heart of Winter Haven, this hotel is 1.6 mi (2.6 km) from Legoland Florida and 1.9 mi (3.1 km) from Chain of Lakes Park. Indigo's Family Fun Center ...

              Lake Roy Beach Inn$78

              Lake Roy Beach Inn$78
              Hampton Inn Winter Haven

              Hampton Inn Winter Haven

              202 Cypress Gardens Blvd, Winter Haven
                2.5 out of 5.0
                 
                 

                Located in the heart of Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Legoland Florida is 3.1 mi (5 km) ...

                Hampton Inn Winter Haven$135

                Hampton Inn Winter Haven$135
                Economy Suites

                Economy Suites

                1901 Cypress Gardens Blvd, Winter Haven
                  2.0 out of 5.0
                   
                   

                  Situated in Winter Haven, this motel is 1.6 mi (2.5 km) from Legoland Florida and 1.9 mi (3.1 km) from Chain of Lakes Park. Indigo's Family Fun Center is 2.2 ...

                  Rodeway Inn and Suites

                  Rodeway Inn and Suites

                  1911 Cypress Gardens Blvd, Winter Haven
                    1.5 out of 5.0
                     
                     

                    Situated in the suburbs, this motel is 1.6 mi (2.5 km) from Legoland Florida and 1.9 mi (3.1 km) from Chain of Lakes Park. Indigo's Family Fun Center is 2.2 ...

                    Rodeway Inn and Suites$60

                    Rodeway Inn and Suites$60
                    Americas Best Value Inn-Winter Haven

                    Americas Best Value Inn-Winter Haven

                    2275 8th St NW, Winter Haven
                      2.0 out of 5.0
                       
                       

                      Located in the heart of Winter Haven, this motel is 2.6 mi (4.2 km) from Indigo's Family Fun Center and 3 mi (4.8 km) from Willowbrook Golf Course. Chain of ...

                      Top Flight Deals

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