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 74 results

31 - 40 of 74 results

Orlando Magic

Central Florida’s Top Sports Experiences

Catch major sports action in and around Kissimmee all year long. From NBA basketball to minor league hockey, it's easy to get in on the game.

A person pulls a book out of a shelf. — Discover stories that enhance your Kissimmee adventure

Discover Must-Visit Bookstores in Kissimmee for a Literary Adventure

Enhance your Kissimmee adventure with a literary twist! Discover indie bookstores where stories unlock secret speakeasies, spark community connections, and unleash epic comic book quests.

A large green roller coaster travels over water on a sunny day in Kissimmee.

Fan Favorites: The 3 Most Thrilling Roller Coasters

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Woman golfer lines up a putt on a sunny day at the Omni Orlando Resort at ChampionsGate in Kissimmee, Florida, with the resort’s luxury hotel visible in the background. — Focus meets finesse at the Omni Orlando Resort at ChampionsGate, where scenic greens and world-class hospitality set the stage for a perfect game.

Fore Incredible Kissimmee Golf Vacation Ideas

Planning a golf getaway in Kissimmee? Here are a few must-tee courses we think are a real hole-in-one.

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!

Three women take a selfie at Boardwalk Plaza in Kissimmee

Savor & Stroll: A Historic Walking Tour of Downtown Kissimmee

Explore Downtown Kissimmee’s rich history and food scene on a walking tour. From iconic landmarks to delicious local bites, there’s always more to discover in the heart of Florida!

Family eating a meal together next to a pool at their vacation home in Kissimmee, Florida. — Find the perfect home-away-from-home with Jeeves Florida Vacation Rentals.

Kissimmee’s Most Fun-Yet-Affordable Vacation Homes

Planning an affordable Central Florida vacation? No problem! Vacation homes don’t have to break the bank and can often offer more value than a hotel.

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

The Most Luxurious Vacation Home Rentals in Kissimmee

When it comes to vacation home rentals, you may think you’ve seen it all, but have you ever seen a vacation rental with its own indoor basketball court? Elevate your expectations with the crème de la crème of Kissimmee's vacation home rentals!

downtown st cloud — Downtown St. Cloud

Downtown St. Cloud's Ultimate Sports Bar Guide

From family-friendly vibes and classic sports bar fun to a tropical retreat right in St. Cloud, FL, Sidelines Sports Grill, Garage Bar St. Cloud, and Island Cloud Grill promise great food, cold drinks, and vibrant game nights, ensuring a great experience for every fan.

A group of six children stand side by side on a brick street at Old Town Kissimmee in the evening, holding balloon animals with string lights and colorful storefronts behind them. — Six smiles, a pocketful of balloon animals, and an Old Town night just getting started.

8 Toddler-Friendly Restaurants in Central Florida

Toddlers are full of energy, and mealtime is no exception! Check out these toddler-friendly restaurants in Central Florida to make mealtime a great time for everyone.