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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1 - 10 of 25 results

1 - 10 of 25 results

Group of friends celebrating the holidays with sparklers and wine around a festive dinner table decorated with candles and Christmas lights. — Ring in the holidays with good food, bright lights, and even brighter smiles during your stay in Kissimmee.

Host Your Next Meeting in Kissimmee and Experience Holiday Magic

Combine productive meetings with the festive spirit of Central Florida’s top attractions and local holiday events.

Cowgirl at Silver Spurs Rodeo.

Rodeo Experiences in Kissimmee

Experience thrilling rodeo events in Kissimmee, Florida, from bull riding and barrel racing at Silver Spurs Arena to family-friendly cowboy fun.

Attendees at classroom-style tables watch a four-person panel onstage under crystal chandeliers, with Reunion Resort & Golf Club logos on two large screens. — Crystal chandeliers, dual screens, and room for a crowd make the Grande Ballroom a natural fit for general sessions and panel discussions.

Meetings Become Experiences at Reunion Resort in Kissimmee

Set across 2,300 acres in Kissimmee, Reunion Resort & Golf Club blends flexible meeting space, villa-style stays, three signature golf courses, and rooftop dining, so every moment of your event becomes a chance to connect.

Corporate Meetings and other Special Event Services

Kissimmee's grandest home rentals are event-ready spaces that easily accommodate special occasions and corporate gatherings.

Colorful fireworks burst across a dark night sky, with bright streaks of red, blue, green, and gold radiating outward. — A sky full of fireworks lights up the night, turning the celebration into a sparkling finale of color and energy.

The Best New Year’s Eve Fireworks Shows in Central Florida

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Two knights sword-fighting on the backs of horses at Medieval Times Dinner & Tournament — Catch a showtime of Medieval Times Dinner & Tournament

Epic Feasts & Battles at Medieval Times Dinner & Tournament

Step into the castle, feast like royalty, and watch an epic battle of gallant knights and old-world chivalry at Medieval Times Dinner & Tournament.

A stylish entertainment venue with pool tables, a bowling alley, and large-screen TVs glowing under red and blue lights in Kissimmee, Florida. — Enjoy a night of friendly competition with bowling, billiards, and big-screen entertainment at this vibrant venue in Kissimmee.

Food, Fun & Games at Kings Dining & Entertainment

With good food, creative cocktails, and a range of games with a high-end spin, Kings Dining & Entertainment in Orlando makes for a fun afternoon or night out.

Luke Boden kicks a soccer ball on the footgolf course at Reunion Resort. — Footgolf is a unique experience for all sports enthusiasts, especially soccer fans.

Luke Boden: A Tour of Kissimmee Sports Venues

Tag along as soccer coach Luke Boden visits key Kissimmee sports venues.

Red Mustang on display during a car show at Old Town Kissimmee — Catch a car show at Old Town Kissimmee

Car Shows at Old Town Entertainment District

Experience the best Kissimmee car shows at Old Town Entertainment District, where classic cars, hot rods, muscle cars, and vintage vehicles shine every week with free admission — alongside family-friendly attractions, dining, and live music.

Three meeting attendees walking in the Gaylord Palms Convention Center — Gaylord Palms Resort & Convention Center

Discover Why Kissimmee Is the Ultimate Destination for Meetings and Conventions

Uncover the charm of Kissimmee with easy access, unique venues, and plenty of opportunities for fun in the sun!