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.

31 - 40 of 47 results

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.

A two story Mediterranean style vacation home sits in the back ground, with a pool, chairs and fire pit in the foreground at dusk. — Enjoy the comforts of a Kissimmee Vacation Home Rental

Vacation Homes in Kissimmee for Spring Break

It won’t be long before spring has sprung, and that can only mean one thing: spring break! You can have everything you’ve ever dreamed of in a vacation, right here in Kissimmee.

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.

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida. — Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.

Influencer Itinerary: 4 Days of Outdoor Adventure & Indoor Leisure

Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

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

Modern two-story vacation home in Kissimmee at sunset, with warm exterior lighting, a spacious driveway, and an upper-level balcony. — A golden-hour welcome. This is what arriving in the Vacation Home Capital of the World feels like.

Top 5 Most Unique Amenities at The Bear’s Den Resort Orlando

Whether you’re visiting Central Florida to escape the cold weather or planning your next vacation with the whole family, The Bear’s Den Resort Orlando is the ideal spot for luxury accommodations.