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.

31 - 40 of 47 results

Exterior entrance of Meliã Orlando Celebration, framed by palm trees and a circular fountain in front of the hotel. — Arrive in style at Meliã Orlando Celebration, where palm-lined paths lead straight into vacation mode.

Top 5 Reasons to Stay at Meliã Orlando Celebration During Your Central Florida Vacation

Central to everything, Meliá Orlando Celebration boasts fine dining, pet-friendly accommodations, and the perfect spot to relax.

two fruity drinks being enjoyed poolside — Enjoy a fruity poolside drink at the Meliã Orlando Celebration

Top 5 Resorts with the Best Pool Bars

Sunny Kissimmee wouldn’t be complete without plenty of pool bar options; here are a few of the most amazing pool bars in the area.

A family enjoying an outdoor meal together at a restaurant patio, smiling and talking over drinks and plates of food on a sunny day. — Good food, good laughs, and that laid-back Florida patio glow. Moments like this taste even better than the barbecue.

3 Spots with the Best Live Entertainment in Downtown Kissimmee

Downtown Kissimmee is not just a destination; it's an experience waiting to be explored.

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

3 Common Myths About Celebration

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!

People gather for live entertainment in Old Town Kissimmee — Old Town Kissimmee is a great place for live entertainment

Top 9 Places to Watch Live Entertainment in Kissimmee

See top spots for exciting live entertainment, from major bands to local live music to popular stand-up comedians and beyond. It's always showtime in Kissimmee!

Father and son at the park.

9 Things to Do with Dad in Kissimmee

Celebrate Father's Day the Kissimmee way!

8 Hotels Near Disney World in Kissimmee, Florida

These eight hotels provide roomy, comfortable accommodations just minutes from world-famous theme parks and come with unique amenities to make your vacation exactly what you need.

Smiling girl in a sun shower with an umbrella. — Don't let a little rain ruin your Kissimmee vacation

6 Fun Vacation Things to do on a Rainy Day in Florida

Even in a downpour, there's family fun to be had in Kissimmee — just don't forget your umbrella!