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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21 - 30 of 36 results

21 - 30 of 36 results

A two story Mediterranean style vacation home sits in the back ground, with a pool, chairs and fire pit in the foreground at dusk. — Enjoy the comforts of a Kissimmee Vacation Home Rental

Top Vacation Homes in Kissimmee for Spring Break

Find the best Kissimmee vacation rental for your spring break getaway.

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida. — Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.

Influencer Itinerary: 4 Days of Outdoor Adventure & Indoor Leisure

Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Bump Up the Fun with a Blissful Three-Day Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

Two people lounging by the pool at the Gaylord Palms Resort and Convention Center enjoying drinks and food. — Enjoying drinks and food poolside at the Gaylord Palms Resort and Convention Center

A Three-Day Itinerary for a Quiet Getaway

There’s a quieter stretch on the Kissimmee calendar when the pace softens, the weather cooperates, and the destination feels refreshingly open. Fewer crowds, easier reservations, and more room to enjoy familiar favorites make this an ideal time for a long weekend or spontaneous escape. This three-day itinerary highlights how Kissimmee shines when timing does the work, and everything feels just a little easier.

Kimberly J. Brown smiles in surprise as two baby goats hop onto the table while she paints during a painting with goats experience at Alaska Farms. — A little goat interference never hurt the creative process! Kimberly J. Brown gets a surprise assist from some curious kids at Alaska Farms.

A Touch of Kissimmee Magic with Kimberly J. Brown

Being normal is vastly overrated, and so is a basic vacation. Actress Kimberly J. Brown casts a spell of fun over Kissimmee with castles, goats, and Halloween-ready adventures.

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

3 Common Myths About Celebration

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The exterior of The One by Magical Vacation Homes features a large horseshoe paved driveway, a large entryway, and a couple balconies. — The One at Magical Vacation Homes

6 Unforgettable Vacation Homes for Your Next Getaway to Florida

Explore exceptional homes from Magical Vacation Homes, where luxury, unique amenities, and affordability come together for an unforgettable vacation experience.

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.

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!