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 43 results

1 - 10 of 43 results

Playground at Kissimmee Lakefront Park

Todo lo que puedes hacer en Lakefront Park en Kissimmee

¡Vive la experiencia del Lakefront Park en Kissimmee! Sumérgete en la belleza de Lake Toho mientras disfrutas de pesca, paseos escénicos, y momentos inolvidables en familia. Además, descubre los sabores locales en este pintoresco refugio al aire libre.

Dr. Laura and her family on an airboat at golden hour

A Family Road Trip to Kissimmee

Join Dr. Laura Scott and her family on a road trip to Kissimmee, Florida, where family fun meets relaxation, local flavor, and the kind of sunshine that makes every moment brighter.

Kyla Kenedy sits to eat a plate of tacos while two cameramen film the shot. — Behind the scenes of the personal chef experience at Kyla's vacation home.

Kyla Kenedy: Top Luxury Experiences Around Kissimmee

Discover some of the most luxurious ways to unwind, indulge, and elevate your getaway in Kissimmee. Episode two of The Kissimmee Experience highlights several standout experiences that showcase the destination’s upscale side.

A sunny tree-lined street with colorful homes and businesses in Kissimmee, Florida.

Celebration, Florida: A Town Like No Other

With tree-lined streets, captivating architecture, and a welcoming mix of shops and restaurants, Celebration invites visitors of all ages to explore.

Red Mustang on display during a car show at Old Town Kissimmee — Catch a car show at Old Town Kissimmee

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.

A mother and child run toward the swimming pool

Enjoy Kissimmee’s Resort Pools with a Day Pass

Looking for a way to unwind poolside at a Kissimmee resort? Discover top spots offering day passes so you can enjoy the luxurious amenities Kissimmee resorts have to offer.

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

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.

A bright vintage car drives past the colorful Old Town entrance arches in Kissimmee, with the Ferris wheel and visitors in the background. — Rolling into Old Town style, where classic cars and classic Florida fun cruise side by side.

Top Car Shows and Automotive Experiences in Kissimmee

Kissimmee is a dream destination for car lovers. From weekly meetups and classic-car cruises to world-famous auctions and auto attractions, the area is full of experiences that get engines — and enthusiasts — fired up.

Children holding freshly made s’mores at a picnic table, with gooey marshmallows and chocolate between graham crackers. — A classic campfire moment, sweet and wonderfully sticky.

Top Spots to Set Up Camp in Kissimmee

Enjoy outdoor adventures by day, then sleep under the stars at one of Kissimmee's top camping spots.

A modern luxury vacation home at dusk featuring a glowing blue resort-style pool with a waterfall, fire feature, palm trees, lounge chairs, and illuminated outdoor living spaces. — 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.

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.