Kissimmee Area Holidays 2025 & 2026

Kissimmee is a city in Central Florida, situated about 18 miles south of Orlando. It’s a favoured destination for Orlando holidays, particularly those seeking villa accommodations. From the prestigious Champions Gate and Reunion Resort to newer communities like Windsor Island, as well as mid-range options like Windsor Hills, Kissimmee offers a range of options to suit every traveller. Dubbed the Vacation Home Capital of the World, it’s a hotspot for comfort and convenience.

Our Florida car hire packages offer the most convenient way to explore Kissimmee. This allows easy access to Orlando’s famous theme parks such as Walt Disney World and Universal Orlando Resort, as well as local attractions like Old Town Kissimmee, Gatorland, and Island H2O Water Park.

The best time to visit Kissimmee is from March to April for mild weather and spring festivities or October to November for cooler temperatures and Halloween events, such as Halloween Horror Nights at Universal Orlando Resort, Howl-O-Scream at SeaWorld, and Mickey’s Not-So-Scary Halloween Party at Walt Disney World. While summer attracts many visitors, it brings high humidity, frequent rain, and large crowds.

Kissimmee boasts attractions beyond the nearby theme parks, including:

• Island H2O Water Park: A high-tech water park featuring interactive slides, a lazy river, wave pools, and cabanas.
• Gatorland: Known as the Alligator Capital of the World, it offers wildlife encounters, shows, and a thrilling zip line over an alligator marsh.
• Medieval Times Dinner & Tournament: Dine on a medieval-style feast while enjoying live jousting and sword-fighting performances.
• Boggy Creek Airboat Adventures: Explore Florida’s wetlands on an exhilarating airboat ride, with opportunities to spot wildlife and enjoy sunset or night tours.
• Old Town: A nostalgic entertainment complex featuring shops, restaurants, rides, and weekly car shows.
• Fun Spot America: A family-friendly amusement park with roller coasters, go-karts, and an arcade.
• Kissimmee Lakefront Park: A scenic park offering fishing, boating, biking, and picturesque picnic spots.

Kissimmee provides diverse shopping experiences, including:

• Kissimmee Value Outlet Shops: Affordable options like Bealls Outlet and Liberty Tourist Outlet.
• The Loop: An open-air centre with retailers such as Kohl’s, JCPenney, and the Nike Clearance Store, plus dining and a cinema.Plaza del Sol: Over 50 speciality shops including Ross Dress for Less and Burlington.
• Lake Buena Vista Factory Stores: Outlet shopping featuring brands like Gap and Nike, with convenient free parking.
• Celebration Town Center: Quaint boutiques such as Market Street Gallery and Little Thimble Craft Studio.

Explore these fantastic destinations near Kissimmee:

• Wekiwa Springs State Park: Approximately 38 miles from Kissimmee, Wekiwa Springs offers a stunning escape into nature with emerald-green springs, lush hammocks, and scenic trails.
• St. Augustine: Discover the oldest city in the U.S., with cobblestone streets and historic landmarks like Castillo de San Marcos. Situated 128 miles from Kissimmee, the two hour journey is ideal for a historical day trip.
• Kennedy Space Center: Located on Merritt Island, about an hour from Orlando, the Kennedy Space Center offers a fascinating experience for space enthusiasts. Highlights include NASA exhibits, launch viewing opportunities, and immersive displays celebrating human space exploration.
• Crystal River: Roughly 90 miles (1.5 hours) from Kissimmee, Crystal River is renowned for its pristine springs and winter manatee gatherings. Visitors can swim or snorkel alongside these gentle creatures, especially in the Crystal River National Wildlife Refuge.
• Tampa: Situated about 75 miles (1.5 hours) from Kissimmee, Tampa offers a vibrant mix of attractions including Busch Gardens, the Florida Aquarium, the Tampa Riverwalk, and historic Ybor City. 
• Clearwater Beach: Clearwater Beach, approximately 100 miles (2 hours) from Kissimmee, is famed for its powdery white sand and tranquil, shallow waters. It’s perfect for families, sunbathers, and water sports enthusiasts, offering a quintessential Florida beach experience.
• St. Petersburg: Known for its beautiful waterfront parks, pristine beaches, and vibrant arts scene, St. Petersburg is home to the renowned Salvador Dalí Museum, which houses an impressive collection of surrealist art. It’s located roughly 95 miles from Kissimmee.
• Daytona Beach: About 70 miles (1.5 hours) from Kissimmee, Daytona Beach offers a mix of beach relaxation and motorsports culture. Don’t miss the Daytona International Speedway for tours and an immersive look at NASCAR history.

Kissimmee is typically around 10 miles from Walt Disney World. Some villa communities like Windsor Hills and Emerald Island are even closer, located within 4 miles of the park.

Universal Orlando Resort is approximately 17 miles from Kissimmee. Villa communities such as Storey Lake Resort and Bella Vida Resort are slightly closer, at about 15 miles away.

Orlando International Airport lies approximately 13 miles from Kissimmee.