Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Kissimmee Vacations

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

Hotwire can help you find your travel bliss with Kissimmee 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 Kissimmee

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 Kissimmee 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 Kissimmee well.

Kissimmee Flight + Hotel packages

Top Hotel Deals

See all 2,271 Hotels in Kissimmee
Mystic Dunes Resort & Golf Club by Diamond Resorts

Mystic Dunes Resort & Golf Club by Diamond Resorts

7600 Mystic Dunes Lane, Kissimmee
    3.5 out of 5.0
     
     

    Set on 600 lushly landscaped acres near Celebration, Mystic Dunes Resort & Golf Club by Diamond Resorts is just 2 miles from Walt Disney World Resort and a short ...

    Mystic Dunes Resort & Golf Club by Diamond Resorts$104

    Mystic Dunes Resort & Golf Club by Diamond Resorts$104
    Maingate Lakeside Resort

    Maingate Lakeside Resort

    7769 W Irlo Bronson Memorial Hwy, Kissimmee
      3.0 out of 5.0
       
       

      Sprawling across 24 acres in Kissimmee, this Mediterranean-style hotel is located 2 miles from Walt Disney World Resort, and within 17 miles of SeaWorld and ...

      Maingate Lakeside Resort$42

      Maingate Lakeside Resort$42
      Red Lion Hotel Orlando - Kissimmee Maingate

      Red Lion Hotel Orlando - Kissimmee Maingate

      7300 W Irlo Bronson Hwy, Kissimmee
        3.0 out of 5.0
         
         

        Located in the heart of Kissimmee, this motel is 2.7 mi (4.3 km) from Disney's Animal Kingdom® Theme Park and within 6 mi (10 km) of Disney's Blizzard Beach ...

        Red Lion Hotel Orlando - Kissimmee Maingate$54

        Red Lion Hotel Orlando - Kissimmee Maingate$54
        Baymont by Wyndham Celebration

        Baymont by Wyndham Celebration

        7601 Black Lake Road, Kissimmee
          3.0 out of 5.0
           
           

          Situated in Kissimmee, this hotel is 2.1 mi (3.4 km) from Disney's Animal Kingdom® Theme Park and within 6 mi (10 km) of Disney's Hollywood Studios® and Disney's ...

          Baymont by Wyndham Celebration$58

          Baymont by Wyndham Celebration$58
          The Grand Orlando Resort at Celebration

          The Grand Orlando Resort at Celebration

          2900 Parkway Blvd, Kissimmee
            3.5 out of 5.0
             
             

            This 23-acre resort is 1.5 miles (2.4 kilometers) from Walt Disney World Resort and across from Celebration with its restaurants, shops, cafes and theaters.

            The Grand Orlando Resort at Celebration$53

            The Grand Orlando Resort at Celebration$53
            Reunion Resort, A Salamander Golf & Spa Resort

            Reunion Resort, A Salamander Golf & Spa Resort

            7593 Gathering Drive, Kissimmee
              5.0 out of 5.0
               
               

              Reunion Resort, A Salamander Golf & Spa Resort is a 13-minute drive from Walt Disney World Resort, and 20 minutes from SeaWorld® Orlando and Universal Orlando ...

              Reunion Resort, A Salamander Golf & Spa Resort$142

              Reunion Resort, A Salamander Golf & Spa Resort$142
              Caribe Cove Resort by Wyndham Vacation Rentals

              Caribe Cove Resort by Wyndham Vacation Rentals

              9000 Treasure Trove Ln, Kissimmee
                3.5 out of 5.0
                 
                 

                Caribe Cove Resort by Wyndham Vacation Rentals is nestled within a tranquil wooded landscape, a 15-minute drive from Disney's Animal Kingdom Theme Park and Disney's ...

                Caribe Cove Resort by Wyndham Vacation Rentals$119

                Caribe Cove Resort by Wyndham Vacation Rentals$119
                Flamingo Waterpark Resort

                Flamingo Waterpark Resort

                2261 E. Irlo Bronson Memorial Hwy, Kissimmee
                  3.0 out of 5.0
                   
                   

                  Conveniently located just 5 minutes from downtown Kissimmee and 20 minutes from Orlando, the Flamingo Waterpark Resort is an ideal Florida destination.

                  Flamingo Waterpark Resort$45

                  Flamingo Waterpark Resort$45
                  Magic Moment Resort and Kids Club

                  Magic Moment Resort and Kids Club

                  5200 West Irlo Bronson Memorial Highway, Kissimmee
                    3.0 out of 5.0
                     
                     

                    Situated on the Strip, this hotel is within 2 mi (3 km) of Museum of Military History, Fun Spot America, and Old Town. Capone's Dinner Show and Lake Buena Vista ...

                    Magic Moment Resort and Kids Club$45

                    Magic Moment Resort and Kids Club$45
                    Magical Memories Villas

                    Magical Memories Villas

                    Various Addresses, Kissimmee
                      3.0 out of 5.0
                       
                       

                      Located in the heart of Central Florida attractions, Magical Memories Villas are within 8 miles of Walt Disney World Resort.

                      Top Flight Deals

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