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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Madilynns Craft Coffee Shop

Celebrating Female-Led Businesses in Downtown St. Cloud

Among the many reasons to celebrate this district near Kissimmee, Florida, is the presence of several successful women-owned businesses that have made their mark on the town.

A family enjoys an airboat ride through the wetlands at Wild Florida, smiling and pointing at wildlife in the distance. — A family sets out on an exciting airboat adventure at Wild Florida, gliding across the headwaters of the Everglades to spot native wildlife and soak in Kissimmee’s natural beauty.

Unwrap the Joy of Kissimmee This Holiday Season

Discover how to make this holiday season memorable with unique gift ideas and unforgettable experiences in Kissimmee. Celebrate Small Business Saturday, explore charming shops, indulge in local flavors, and create lasting memories with your loved ones!

Playground at Kissimmee Lakefront Park

Day of Wellness and Relaxation Across Downtown Kissimmee & St. Cloud

Discover a day of relaxation in Downtown Kissimmee and St. Cloud, Florida. From lakeside strolls to yoga, tasty bites, and self-care, unwind in style.

Shoppers stroll along a palm-lined outdoor shopping promenade, passing luxury storefronts while carrying branded shopping bags on a sunny day. — Sunlit strolls and stylish finds turn shopping into a vacation-worthy pastime.

The Ultimate Shopping Day at Orlando Vineland Premium Outlets®

Orlando Vineland Premium Outlets® is Central Florida’s only upscale, open-air outlet shopping destination, featuring a dazzling mix of boutique-style luxury and must-have brands.

Exterior of Mall at Millenia with palm trees and blue sky — Indulge in luxury shopping at the Mall at Millenia

The Mall at Millenia: Luxe Shopping, Dining & More

Find your favorite designer stores, a mix of great dining, and top-tier services from self-care to personal styling at The Mall at Millenia in Orlando.

A man and child run into the pool — Splash and play all day in Kissimmee

When’s the Best Time to Visit Kissimmee?

Whether it’s a spring break, a summer vacation, a fall road trip, or a winter escape from cold weather, every season in Kissimmee offers opportunities for enjoyment.

Family walking down sidewalk at the Promenade at Sunset Walk — Enjoy shopping, dining, and entertainment at Promenade at Sunset Walk

Kissimmee Shopping Guide

From outlet malls to specialty boutiques to local favorites and national brands, there's a shopping experience for everyone in Kissimmee. Find out everything you need to know in this handy guide.

Dog treats. — Woof Gang Pastries specializes in gourmet dog treats for your pup

How To Plan A Paw-Some Vacation in Kissimmee, Florida

We want to make sure that every member of your family has the best time ever while vacationing in Kissimmee. Here are a few things we have to offer our four-legged visitors.

A women and two children walk in front of a rollercoaster at Sea World — Ride the Mako roller coaster at SeaWorld

Your Guide to Planning a Central Florida Vacation

With tips, ideas, a handy checklist, and more, our vacation planning guide will get those wheels turning and mind reeling about all the fun things to plan during your Kissimmee getaway.

Two people float and play in a private vacation home pool, splashing water while relaxing in bright inflatable tubes on a sunny Florida day. — Pool time hits its happy place in Kissimmee’s vacation homes.

Your Ultimate Vacation Planning Checklist

Check out this helpful Vacation Planning Checklist to inspire excitement when preparing for your next trip to Kissimmee, Florida!