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Winter Garden Vacations

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

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

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 Garden 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 Garden well.

Winter Garden Flight + Hotel packages

Top Hotel Deals

See all 5,979 Hotels in Winter Garden
Liki Tiki Village by Diamond Resorts

Liki Tiki Village by Diamond Resorts

17777 Bali Blvd, Winter Garden
    3.5 out of 5.0
     
     

    Liki Tiki Village by Diamond Resorts is a 64-acre hotel in southwest Orlando, a half-hour drive from Orlando International Airport. Guests can drive 10 minutes ...

    Liki Tiki Village by Diamond Resorts$58

    Liki Tiki Village by Diamond Resorts$58
    The Grove Resort & Spa Orlando - Spacious 1, 2 & 3-Bedroom Suites

    The Grove Resort & Spa Orlando - Spacious 1, 2 & 3-Bedroom Suites

    14501 Grove Resort Avenue, Winter Garden
      4.0 out of 5.0
       
       

      5-minute drive from Walt Disney World® Resort

      TownePlace Suites Orlando @ Flamingo Crossings West Entrance

      TownePlace Suites Orlando @ Flamingo Crossings West Entrance

      13295 Flamingo Crossings Boulevard, Winter Garden
        3.5 out of 5.0
         
         

        Situated in Winter Garden, this hotel is within 9 mi (15 km) of Disney's Hollywood Studios®, Epcot®, and Disney Springs®. Walt Disney World® and Magic Kingdom® ...

        TownePlace Suites Orlando @ Flamingo Crossings West Entrance$71

        TownePlace Suites Orlando @ Flamingo Crossings West Entrance$71
        SpringHill Suites Orlando at Flamingo Crossing/West Entrance

        SpringHill Suites Orlando at Flamingo Crossing/West Entrance

        13279 Flamingo Crossings Boulevard, Winter Garden
          3.0 out of 5.0
           
           

          Situated in Winter Garden, this hotel is within 9 mi (15 km) of Disney's Hollywood Studios®, Epcot®, and ESPN Wide World of Sports. Disney Springs® and Walt ...

          SpringHill Suites Orlando at Flamingo Crossing/West Entrance$79

          SpringHill Suites Orlando at Flamingo Crossing/West Entrance$79
          Orange County National Lodge

          Orange County National Lodge

          16325 Phil Ritson Way, Winter Garden
            3.0 out of 5.0
             
             

            Situated in Winter Garden, this golf lodge is in the same area as Walt Disney World®, Magic Kingdom® Park, and Disney's Magnolia Golf Course. Area attractions ...

            Orange County National Lodge$60

            Orange County National Lodge$60
            Edgewater Hotel

            Edgewater Hotel

            99 W Plant St, Winter Garden
              2.5 out of 5.0
               
               

              Situated near the airport, this bed & breakfast is steps from Winter Garden Heritage Museum, Garden Theatre, and Central Florida Railroad Museum. Winter Garden ...

              Edgewater Hotel$98

              Edgewater Hotel$98
              Palisades - A Two and Three Bedroom Condo Resort

              Palisades - A Two and Three Bedroom Condo Resort

              14200 Avalon Road, Winter Garden
                3.5 out of 5.0
                 
                 

                Located in West Kissimmee, this condo building is within 12 mi (20 km) of ESPN Wide World of Sports, Disney's Boardwalk, and Walt Disney World®. Magic Kingdom® ...

                Magical Palisades Resort Condo 2 Bedroom IPG Florida

                Magical Palisades Resort Condo 2 Bedroom IPG Florida

                14200 Avalon Road 215, Winter Garden
                  3.5 out of 5.0
                   
                   

                  Located in West Kissimmee, this condo building is within 9 mi (15 km) of Lake Davenport, ChampionsGate Golf Club, and Disney's Animal Kingdom® Theme Park. Disney's ...

                  B Resort and Spa located in Disney Springs® Resort Area

                  B Resort and Spa located in Disney Springs® Resort Area

                  1905 Hotel Plaza Blvd, Lake Buena Vista
                    4.0 out of 5.0
                     
                     

                    Walking distance to 2 Walt Disney World Parks

                    B Resort and Spa located in Disney Springs® Resort Area$65

                    B Resort and Spa located in Disney Springs® Resort Area$65
                    Caribe Royale All-Suite Hotel & Convention Center

                    Caribe Royale All-Suite Hotel & Convention Center

                    8101 World Center Dr, Orlando
                      4.0 out of 5.0
                       
                       

                      This all-suite hotel with its own convention center is within 6 miles of Walt Disney World Resort, Universal Orlando, SeaWorld, and the Orlando Convention ...

                      Caribe Royale All-Suite Hotel & Convention Center$79

                      Caribe Royale All-Suite Hotel & Convention Center$79

                      Top Flight Deals

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