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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A mother and her young son enjoy a meal together while riding the Brightline train, with sunlight streaming through the window and a scenic view outside. — Enjoy a comfortable ride aboard Brightline, savoring snacks and scenery on the way to Kissimmee.

Getting Around Kissimmee by Train: Brightline, SunRail, and More

Discover how to ride the rails in Kissimmee, from fast and convenient train services like Brightline and SunRail to iconic theme park rides like the Walt Disney World® Monorail. Whether you're traveling around Central Florida or hopping aboard a rail-themed adventure, this guide has your ticket.

Love is what makes the world go round at ICON Park, near Kissimmee, Florida.

Romance in Kissimmee This Valentine’s Day

Celebrate Valentine's Day in Kissimmee, Florida, with thrills, sweets, and more romantic fun!

Christmas tree in the Gaylord Palms Resort

Christmas at Gaylord Palms 2025: Rudolph the Red-Nosed Reindeer™ and More Holiday Fun

From Nov. 14, 2025 to Jan. 7, 2026, Christmas at Gaylord Palms transforms the resort into a holiday wonderland featuring Rudolph the Red-Nosed Reindeer™, dazzling lights, and family fun.

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.

Santa's Little Helper cocktail

Holiday Cocktail Recipes from Kissimmee’s Best Mixologists

Warm up the holidays with festive drink recipes straight from Kissimmee’s top bars and restaurants!

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.

Celebrate Mother’s Day Weekend: 48 Hours of Family Fun in Kissimmee

Treat the special mom, mother figure, or loved one in your life to an unforgettable Mother’s Day weekend in Kissimmee. From relaxing spa moments to thrilling adventures, discover two days of exciting activities, delicious dining, and memorable experiences for the whole family.

A beautiful vacation home rental in Kissimmee — A Kissimmee Vacation Home is your home away from home

10 Reasons to Choose a Vacation Home Rental in Kissimmee

Imagine waking up to a picturesque lake view or watching the sunrise on the golf course from your own private balcony of your vacation home rental.

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.