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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51 - 60 of 247 results

51 - 60 of 247 results

Brightine

Helpful Guide for Brightline Orlando

Brightline makes it easier than ever to explore Florida with modern, eco-friendly trains connecting top destinations in the state. With convenient service between Orlando and major cities like Miami, West Palm Beach, and Fort Lauderdale, Brightline is a stress-free alternative to driving or flying — perfect for visitors looking to experience more of the Sunshine State.

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.

What Kissimmee Halloween Costume Matches Your Personality?

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A family of four smiles and poses together in front of a looping roller coaster at a theme park, with parents holding their two young children. — Big smiles, little thrill-seekers, and a coaster waiting in the wings. This is what a family day of unforgettable fun looks like.

Top Central Florida Theme Park Rides

You'll find great rides for everyone, from laidback experiences for the young and old to fast-paced thrill rides for the brave and bold.

Pouring red wine into a flute from a bottle next a to a flute of white wine

Top Date Night Restaurants in Kissimmee

Add global flair to your date night and let your taste buds lead you on a delicious journey at these romantic restaurants in and around Kissimmee.

Golf course with flag and water — Kissimmee's Famous Golf Courses

Top Golf Courses in Kissimmee

Surrounded by lush greenery and towering trees, Kissimmee golf courses are as scenic as they are challenging. Find the best fairways here.

Top Restaurants in Celebration

From freshly baked biscuits to gourmet charcuterie plates to refreshing ice cream, Celebration's restaurants are sure to please.

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.