Trip Ideas for Your Kissimmee Vacation

Find inspiration for your trip to Central Florida with articles, lists and itineraries featuring things to do and places to explore.

Located minutes from Orlando, Kissimmee is your gateway to Central Florida’s must-do adventures: thrilling airboat rides, vibrant local festivals, family-friendly theme parks, and all the shopping and dining options you could dream of. The hard part is deciding where to start, but that’s where we come in.

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21 - 26 of 26 results

21 - 26 of 26 results

Father and son at the park.

9 Things to Do with Dad in Kissimmee

Celebrate Father's Day the Kissimmee way!

A person pulls a book out of a shelf. — Discover stories that enhance your Kissimmee adventure

Discover Must-Visit Bookstores in Kissimmee for a Literary Adventure

Enhance your Kissimmee adventure with a literary twist! Discover indie bookstores where stories unlock secret speakeasies, spark community connections, and unleash epic comic book quests.

Smiling girl in a sun shower with an umbrella. — Don't let a little rain ruin your Kissimmee vacation

6 Fun Vacation Things to do on a Rainy Day in Florida

Even in a downpour, there's family fun to be had in Kissimmee — just don't forget your umbrella!

A family enjoying an outdoor meal together at a restaurant patio, smiling and talking over drinks and plates of food on a sunny day. — Good food, good laughs, and that laid-back Florida patio glow. Moments like this taste even better than the barbecue.

3 Spots with the Best Live Entertainment in Downtown Kissimmee

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People gather for live entertainment in Old Town Kissimmee — Old Town Kissimmee is a great place for live entertainment

Top Live Entertainment in Kissimmee

See top spots for exciting live entertainment, from major bands to local live music to popular stand-up comedians and beyond. It's always showtime in Kissimmee!

Two men and a woman walk the water front in Celebration. — Enjoy your next meeting or event in sunny Florida.

9 Hotels in Kissimmee for Hosting Your Next Meeting or Event

Where business meets innovation — and a bit of fun! Discover top meeting hotels in Kissimmee with flexible spaces, modern amenities, and unique venues for your next event.