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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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1 - 10 of 29 results
1 - 10 of 29 results
Catch a car show at Old Town Kissimmee
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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.
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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.
When the sun sets, the pool steals the spotlight. Evening swims glow a little brighter with fire features, flowing water, and room to unwind long after dark.
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Top Tier at Reunion: Where the Stay Becomes Part of the Story
In Kissimmee, the Vacation Home Capital of the World®, where space, comfort, and flexibility define the way people travel, Top Tier at Reunion offers a refined way to settle in. These hand-selected luxury homes combine thoughtful design, elevated amenities, and personalized service with the freedom to experience Central Florida on your own terms, from theme park days to nature escapes and unforgettable meals shared around the table.
Plan your next stay in Kissimmee at one of our many vacation homes.
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Where to Stay in Kissimmee: Hotels, Resorts, and Vacation Homes for Every Traveler
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!
Catch a showtime of Medieval Times Dinner & Tournament
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Epic Feasts & Battles at Medieval Times Dinner & Tournament
Step into the castle, feast like royalty, and watch an epic battle of gallant knights and old-world chivalry at Medieval Times Dinner & Tournament.
Cannonballs, sunshine, and your own private pool. This is vacation freedom, Kissimmee-style.
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Your Guide to Hosting the Ultimate Florida Pool Party
Take a dip with your closest friends in an awesome Kissimmee pool. Before splish-splashing the day away, here are a few tips for hosting an unforgettable pool party when you’re vacationing in the Sunshine State.
A family begins their getaway at a spacious Kissimmee vacation home, perfect for creating memories together in the Vacation Home Capital of the World®.
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Find Your Kissimmee Home Base: Stay, Work & Play
Grab your laptop, pack up the kids, and head to Central Florida, where you can stay, work, and play all in one spot.
Enjoy a night of friendly competition with bowling, billiards, and big-screen entertainment at this vibrant venue in Kissimmee.
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Food, Fun & Games at Kings Dining & Entertainment
With good food, creative cocktails, and a range of games with a high-end spin, Kings Dining & Entertainment in Orlando makes for a fun afternoon or night out.
A sky full of fireworks lights up the night, turning the celebration into a sparkling finale of color and energy.