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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31 - 40 of 52 results

31 - 40 of 52 results

Group of friends carrying pool floaties walking along a sidewalk in the sunshine. — Spend some time at the pool when you stay at Margaritaville Resort Orlando.

Savor Island Time at Margaritaville Resort Orlando

Feel transported to the tropics with a stay at Margaritaville Resort Orlando. Swim, sip, and shop your way through this island-inspired resort and soak up all the great amenities.

Three women take a selfie at Boardwalk Plaza in Kissimmee

See, Eat, and Explore Downtown Kissimmee for Less Than $30

Explore Downtown Kissimmee without spending a fortune. A full day of adventure, food, and family fun is waiting — all for less than $30!

A white ceramic coffee mug with a black circle and the words, XO Coffee in white letters in the center, on a wooden tabletop. In the background, there is a faint outline of a neon sign. — Enjoy a coffee while watching tattoo artists at work at XO Coffee Shop.

XO Coffee Shop: Fresh Brews & Tattoos

XO Coffee Shop in Kissimmee blends great coffee with creative tattoo art, offering a welcoming space for everyone. Experience the perfect mix of caffeine, creativity, and community.

A plate of carnitas tostadas garnished with lime, cilantro, and queso fresco at Planet Hollywood in Disney Springs, with the Aerophile balloon visible in the background. — Carnitas Tostadas from Planet Hollywood pair perfectly with sunny skies and vibrant views at Disney Springs.

Celebrating Hispanic Heritage in Kissimmee

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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.

A large family gathers around the Christmas tree in Kissimmee

Kissimmee Vacation Homes for the Holidays

Explore the vacation home rentals available in Central Florida to find the perfect spot to celebrate this holiday season.

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.