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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31 - 40 of 54 results

31 - 40 of 54 results

Dezerland in the Rain — Dezerland

Top Tips for Hurricane Season Travel

If you’re planning on visiting the Sunshine State during hurricane season, check out our FAQ below.

A man and woman toast to their accommodations in Kissimmee — Cheers to good times in Kissimmee

Accommodations in Kissimmee That Go Above and Beyond

Lazy rivers, multilevel pools, in-house theaters, private spas, personal concierge service, and more. These accommodations take your Central Florida vacation to the next level.

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

Themed Vacation Rentals in Kissimmee

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

Aerial view of a resort pool complex with winding lazy river, palm trees, lounge chairs, and blue umbrellas surrounded by lush landscaping. — A bird’s-eye view of laid-back luxury, where winding pools and palm-lined paths set the pace for a perfect resort day.

Top Unique Hotel Experiences in Kissimmee

From lounging in a tropical lagoon to riding water slides to playing footgolf, find fun resort experiences when you stay in Kissimmee, Florida.

A man unloads his car in front of a vacation home as his family enters the home. — Plan your next stay in Kissimmee at one of our many vacation homes.

Where to Stay in Kissimmee

Kissimmee offers lodging to fit any need, from 4-star resorts to motels to vacation rentals. Learn more about all the ways you can stay in Central Florida!

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!

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.

Two people lounging by the pool at the Gaylord Palms Resort and Convention Center enjoying drinks and food. — Enjoying drinks and food poolside at the Gaylord Palms Resort and Convention Center

A Three-Day Itinerary for a Quiet Getaway

There’s a quieter stretch on the Kissimmee calendar when the pace softens, the weather cooperates, and the destination feels refreshingly open. Fewer crowds, easier reservations, and more room to enjoy familiar favorites make this an ideal time for a long weekend or spontaneous escape. This three-day itinerary highlights how Kissimmee shines when timing does the work, and everything feels just a little easier.