An outdoor holiday tree fully decorated on a beautiful Kissimmee day
Celebrate the Holidays

in Kissimmee

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The holiday season is fast approaching, and there’s no better place to celebrate with your loved ones than right here in Kissimmee. Make no mistake about it, Kissimmee is awesome all year long, with outdoor adventures, attractions, sports, and entertainment options waiting for you to discover, but the holiday season is a truly special time here—one that’s full of events that will make your visit absolutely unforgettable.

If you’re looking for the best ways to get in the holiday spirit during your upcoming trip, you’ve come to the right place. Here are the can’t-miss things to do when celebrating the holidays in Kissimmee that will put you at the top of everyone’s nice list!

Enjoy an Old-Fashioned Holiday in Old Town Kissimmee

Old Town Kissimmee illuminated by holiday decorations

Embrace an all-American holiday during Holidays at Old Town. Taking place from November 23rd to December 25th, Holidays at Old Town transforms beautiful Old Town Kissimmee into a winter wonderland—complete with a little fluffy snow! Brick-paved streets are lined with colorful lights and festive decorations hang in the windows of the shops. And at the center of it all is the iconic Old Town Christmas Tree. At over 40-feet tall—and decorated from top to bottom—you’ve never seen anything like this tree! Best of all, while you’re here, you can get some of your holiday shopping done!

Visit Celebration’s Holiday Homes

An interior of a home decorated for the holiday season

For more than two decades, the Holiday Home Tour & Winter Wonderland in Celebration has been a tradition for thousands of locals and visitors to our area. On December 1st and 2nd, you’ll have the opportunity to tour many of Celebration’s beautiful homes—all decorated especially for the holidays! Whether you’re looking for a little inspiration for your own holiday display, or you’re a fan of the New Urbanism architecture of these homes built by the Walt Disney Company, you’re sure to be delighted on this two-hour self-guided tour.  

Explore the St. Cloud Holiday Festival

The first weekend in December is rich with holiday activities. Not only is this when the Holiday Home Tour takes place, it’s also time for the 40th annual St. Cloud Holiday Festival. This festival is a dream come true for holiday lovers! There’s a parade, a crafters market, delicious snacks and treats, family fun, an antique car show, live entertainment, and more. If you’re the type of person who likes being holly and jolly all December long, this festival will get you started on the right foot!

Watch the Kissimmee Festival of Lights Parade

A car drives in the Kissimmee Festival of Lights Parade

One of our favorite annual holiday events in Kissimmee is the Festival of Lights Parade. This year, the parade takes place on December 8th right here in downtown Kissimmee. You and your family can watch as floats representing groups, communities, and businesses from across Kissimmee light up the evening—all lead by our very own Grand Marshall. However, this is more than just a parade. It’s also a chance for kids to meet Santa himself down on Main Street and give him their wish list! There will also be arts and crafts at the Hart Memorial Library, and the lighting of the Monument of the States.

Take in a Seasonal Musical at Osceola Arts

Nothing gets us in a holiday state of mind quite like a musical! And this season at Osceola Arts, you have the chance to see an all-time classic reimagined for the stage—Meredith Willson’s Miracle on 34th Street! Every Friday, Saturday, and Sunday between November 30th and December 23rd, you can watch as Kris Kringle and his friends work to prove he is the real Santa Claus to people all around the world. Sure, you may know this iconic story (and may be able to recite your favorite lines by heart), but this version includes singing and dancing that is definitely going to get your toes tapping!  

Experience the Holiday Spectacular at Gaylord Palms Resort

Children enjoy playing with a life-sized gingerbread man

The holiday season at Gaylord Palms Resort is truly something to behold. From November 16th through January 6th, over two million twinkling lights light up the resort, while magical decorations are on display across the grounds. Kids will love exploring ICE! The indoor winter wonderland complete with ice carving, snow to play in, and special sculptures inspired by the holiday classic, A Christmas Story. Take in the Cirque Dreams Unwrapped Stage Show for thrilling displays of showmanship, zoom down an eight-lane tubing hill in the Alpine Village, decorate your own gingerbread house, visit Santa’s workshop, join the Elf on the Shelf for breakfast, and more! A stay at Gaylord Palms Resort during the holiday season is the gift that keeps on giving!  

So what’s the best part of celebrating the season in Kissimmee? It’s getting to have all of this fantastic festive fun with none of the chilly weather! We can’t wait to share in a little holiday magic with you, right here in Kissimmee. Start planning your vacation today!

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