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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Family gathered around a dining table in a decorated Kissimmee vacation home, enjoying a festive holiday meal together by the Christmas tree. — Celebrate the holidays in comfort and style with family and friends in a beautifully decorated Kissimmee vacation home.

Top 5 Ways to Celebrate the Holidays in a Kissimmee Vacation Home

In the Vacation Home Capital of the World®, the holidays can be a little easier for you and much more memorable for the rest of the family.

Girl sitting in a rocket ship bed at a Kissimmee vacation home.

Themed Vacation Rentals in Kissimmee: Where Imagination Meets Home Comfort

With game rooms, bedrooms, and in-house theaters, these vacation home rentals make for a magical place to stay.

Mother and daughter smiling while planning their next family vacation on a laptop at home. — Plan your next family getaway to Kissimmee, where unforgettable adventures are just a short drive away.

Tips and Tricks to Help You Plan Your Vacation

Planning your big Kissimmee getaway? Here are some handy tips for making the most of your vacay.

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

Revving Up: 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.

Two people sit cross-legged in a bright, minimalist studio practicing alternate nostril breathing as part of a mindfulness or yoga session. — Focused breathwork can bring clarity, reduce stress, and support mental wellness, making it an ideal activity for attendees seeking balance during a busy event. Photo courtesy of Crow Practice.

Breathe Easy: Wellness Tips and Resources for Impactful Meetings

Discover how intentional breathwork — shared by Kristine Iverson, founder of Crow Practice in Kissimmee — can enhance focus, reduce stress, and bring balance to your next event.

A small group of colleagues sits together outdoors, smiling and reviewing printed materials during an informal meeting. — Ideas flow a little easier when the meeting feels more like a catch-up than a conference.

Luxury in Kissimmee: Elevated Experiences for Meeting Planners and Attendees

Discover Kissimmee’s luxury meeting venues, exclusive VIP experiences, and personalized services that elevate every event into an unforgettable escape.

Group of people enjoying an airboat ride through the headwaters of the Everglades near Kissimmee, Florida, gliding over the water with lush green marshes under a clear blue sky. — Feel the rush of adventure on an airboat tour through Kissimmee’s headwaters of the Everglades.

How Kissimmee Blends Business, Fun, and Fresh Ideas

In Kissimmee, meetings go beyond the agenda with unique activations, outdoor adventures, and purposeful experiences that leave a lasting impression on attendees and the community. As Central Florida’s ultimate bleisure destination, hosting here often means record attendance, with participants eager to come early and stay late.

Outdoor lawn at Gaylord Palms Resort & Convention Center at sunset. — Enjoy the artfully crafted outdoor spaces when you stay at Gaylord Palms Resort

4 Reasons to Meet in Kissimmee - The Big, Bold Heart of Florida

A sunny tree-lined street with colorful homes and businesses in Kissimmee, Florida.

3 Common Myths About Celebration

Nighttime scene at Old Town Kissimmee featuring classic cars cruising down the brick streets, colorful shops, and visitors enjoying the lively atmosphere. — Experience the charm of Old Town Entertainment District, where classic car shows, family fun, and vintage vibes light up the night.

Kissimmee Events: Your Year-Round Guide to Must-See Celebrations

Discover the top Kissimmee events, from festivals and rodeos to parades in downtown Kissimmee and more. Plan your trip for unforgettable celebrations all year long!