Kissimmee, in the heart of Central Florida, you’ll find a charming, vibrant city that epitomizes the Sunshine State’s promise of fun, adventure, and relaxation. Kissimmee is an idyllic location for families and solo adventurers, known for its year-round sunshine, natural beauty, and proximity to world-renowned theme parks.

Whether you’re staying in one of our beautiful themed vacation homes or considering booking at one of our bespoke resorts, we invite you to explore the diverse offerings of this magical locale.

1. Explore Old Town Kissimmee

Photo Credit: VIAVAL TOURS

Nestled in the heart of Kissimmee, Old Town captures the classic charm of Florida in a unique and entertaining way. Reminiscent of a classic Florida town from a bygone era, this beloved local attraction is a carefully constructed throwback that offers a mix of nostalgia and fun.

Take a leisurely stroll down brick-lined streets flanked by beautiful, vintage-style buildings. This walking district is home to over 70 unique and affordable shops, where you can find everything from clothing and accessories to collectibles and candy. It’s the perfect spot for picking up a memorable vacation souvenir.

Old Town also boasts a selection of restaurants and bars, offering a diverse range of culinary and nightlife options. Whether you’re in the mood for a classic American burger, Mexican food, or Italian fare, you’ll find a restaurant that satisfies your cravings.

But it’s not just shopping and dining at Old Town. The entertainment is abundant, especially on the weekends. Take a spin on the Ferris wheel, enjoy live music at one of the many outdoor stages, or catch a classic car parade. Every Saturday, the streets of Old Town come alive with the Saturday Nite Classic Car Show and Cruise, a must-see event for automobile enthusiasts.

2. Take an Airboat Tour

For an adventure that truly captures the essence of Florida’s wild, natural beauty, an airboat ride in Kissimmee is an absolute must. These high-speed boats skim across the water’s surface, providing an adrenaline rush and a unique way to explore the Sunshine State’s waterways and wildlife.

One of the best places to embark on this thrilling adventure is at Lake Tohopekaliga, often referred to as Lake Toho or the Everglades. As your airboat slices through the water, your captain will point out fascinating aspects of the surrounding ecosystem. With the wind in your hair and the hum of the boat beneath you, you’ll weave through dense marshes and open waters, discovering corners of Florida’s wilderness that are inaccessible by conventional means.

The highlight of any airboat ride is undoubtedly the opportunity to encounter Florida’s famed alligators in their natural habitat. Along with these ancient creatures, you’ll have the chance to spot various species of birds, turtles, and perhaps even the elusive Florida panther.

3. Get Your Adrenaline Pumping at Fun Spot America

Photo Credit: VIAVAL TOURS

Just a short drive from the heart of Kissimmee, Fun Spot America promises a day filled with thrilling rides, family-friendly games, and unforgettable excitement. Renowned for its personal, friendly feel and a variety of attractions, this amusement park is a popular destination for families, groups, and solo thrill-seekers.

At Fun Spot America, you’ll find an impressive collection of roller coasters and rides catering to all levels of bravery. Daredevils can ride the SkyCoaster, the world’s tallest ride of its kind, combining elements of skydiving and hang-gliding. The park is also home to the only wooden roller coaster in Central Florida, the Mine Blower, which offers an exciting twist on a classic amusement park ride.

Beyond the roller coasters, Fun Spot America offers various other activities. Kids can enjoy a variety of rides in the Kiddie Park, while the entire family can engage in friendly competition at the arcade, which features classic and modern games. And don’t forget ziplining or go-karts!

One of the most appealing aspects of Fun Spot America is its ‘pay-as-you-go’ policy, which means that you only pay for the rides you go on. This way, everyone can tailor their experience to their interests and thrill levels.

4. Relax at Kissimmee Lakefront Park

Photo Credit: Michael Gordon

Kissimmee Lakefront Park is a tranquil oasis in the heart of Central Florida, offering a welcome respite from the hustle and bustle of the city’s other high-energy attractions. Set alongside Lake Tohopekaliga, this scenic park provides various recreational activities and relaxation opportunities for visitors of all ages.

Visitors can enjoy a leisurely walk along the meticulously maintained boardwalk, taking in the beauty of the lush landscape and picturesque lake views. Numerous benches line the path, providing the perfect spots to sit, unwind, and perhaps even catch a glimpse of the local wildlife, such as ducks, turtles, and even alligators.

Children will love the park’s playground areas, which feature modern, safe equipment. With plenty of green space for picnicking, you can easily make a day of your visit.

5. Discover the Biking Trails

Kissimmee’s diverse landscapes provide the perfect backdrop for an invigorating bike ride. Whether you’re an experienced cyclist seeking challenging terrain or a casual biker looking for a leisurely journey, the city’s numerous biking trails cater to all fitness levels and preferences.

Shingle Creek Regional Trail is a local favorite. This multi-use trail extends from Kissimmee to Orlando and offers riders a variety of scenic views. As you pedal through the diverse landscapes, you’ll be enveloped by lush greenery, pass picturesque waterways, and may even spot some of the local wildlife. It’s an experience that seamlessly combines fitness with nature appreciation.

Another popular trail is the Lake Toho Loop. This 19-mile trail encircles Lake Tohopekaliga and takes riders past Kissimmee’s Waterfront Park. The route provides a wonderful opportunity to enjoy the serene lake views, watch local anglers in action, and even take a break at the park.

Kissimmee also offers easy access to the expansive Florida Coast-to-Coast Trail. When completed, this impressive route will stretch over 250 miles across the state, providing a more ambitious journey for dedicated cyclists.

6. Explore the Museum of Military History

Located in the heart of Kissimmee, the Museum of Military History is dedicated to educating, increasing awareness, building knowledge, and promoting appreciation for those who have served in our nation’s military. It’s a fascinating destination for history enthusiasts, families, and anyone interested in understanding the sacrifices of American servicemen and women.

As soon as you enter the museum, you’re immediately immersed in America’s rich military history. The museum houses an extensive collection of exhibits, artifacts, and memorabilia from the Revolutionary Civil Wars to both World Wars and various other historical conflicts.

The Museum of Military History also hosts guest speakers, presentations, and special events, offering visitors an even deeper understanding of our nation’s military history. Consider taking a guided tour in order to fully appreciate the museum. It’s an experience that not only educates but also fosters an appreciation for the service and sacrifices of our military men and women.

7. Unwind at Shingle Creek Regional Park

Photo Credit: Jeff Holcombe

A natural gem in the heart of bustling Kissimmee, Shingle Creek Regional Park offers a peaceful retreat for those seeking to reconnect with nature. Spanning over 456 acres, the park is often referred to as the “northernmost headwaters of the Florida Everglades” and showcases the diverse beauty of Central Florida’s natural landscape.

As you explore the park, you’ll wander through a mix of pine flatwoods, oak hammocks, wetlands, and cypress swamps, all teeming with native wildlife. It’s not uncommon to spot birds, turtles, and even gators during your visit, so be sure to bring your binoculars for a close-up view.

The park features several miles of multi-use trails, perfect for outdoor activities such as walking, running, and biking. With numerous observation decks and picnic areas along the way, you’ll have plenty of opportunities to pause and absorb the tranquility of the surroundings.

For a unique perspective of the park, consider renting a kayak, paddleboard, or canoe and exploring Shingle Creek, the park’s namesake waterway. As you paddle, you’ll enjoy a unique perspective of the park’s wildlife and landscapes, making it a truly immersive natural experience.

8. Visit the Surrounding Theme Parks

While Kissimmee is packed with attractions, it’s also conveniently located near some of the world’s most famous theme parks, making it an ideal base for thrill-seekers and families looking for the perfect day trip.

A short drive away is the magical world of Walt Disney World Resort. Comprising four theme parks – Magic Kingdom, Epcot, Disney’s Hollywood Studios, and Animal Kingdom – and two water parks, Disney World offers endless fun and enchantment for visitors of all ages.

Close by, you’ll also find Universal Orlando Resort. Here, you can immerse yourself in the action-packed world of Universal Studios, journey through the legendary lands of Universal’s Islands of Adventure, or cool off in the tropical paradise of Universal’s Volcano Bay.

For those interested in LEGO, a trip to LEGOLAND Florida Resort is a must. This interactive theme park offers creative hands-on experiences, exciting rides, and shows that are perfect for families with younger children in search of fun things to do on a quintessential Florida vacation.

Each park offers a unique experience, promising a memorable day out. So, step into a world of imagination, adventure, and fun for the whole family, just a stone’s throw away from Kissimmee.

9. Check out the Monument of States

One of the best-known Downtown Kissimmee attractions, the Monument of States is a unique, historical landmark that stands as a testament to unity and patriotism. Built in 1943, during the height of World War II, this 50-foot tower is an intriguing piece of Americana worth exploring.

The idea of the monument was conceived by Dr. Charles Bressler-Pettis, a local civic leader who sought a symbol of unity during a time of global unrest. He asked states, countries, and dignitaries around the world to send local rocks, and the response was overwhelming. The monument consists of these donated stones, minerals, and fossils, some of which bear inscriptions or dedications.

10. Attend a Show at Medieval Times

Take a step back in time and immerse yourself in a world of chivalry, rivalry, and revelry at Medieval Times Dinner & Tournament. Located in Kissimmee, this popular attraction provides a unique dinner show experience that promises to entertain and amaze visitors of all ages.

Medieval Times is set within an 11th-century-style castle. As you walk through the castle doors, you’ll be transported to a time of knights and nobles, horses and falcons, and exciting medieval games.

The heart of the experience is the two-hour grand tournament. As you feast on a four-course, utensil-free meal, you’ll watch six brave knights compete in games of skill, hand-to-hand combat, and thrilling jousting matches. Each audience section is assigned a knight to cheer for, making for an interactive and immersive experience.

The show has an impressive display of falconry and equestrian skills, with beautiful Andalusian horses showcasing their strength and agility.

Magic Awaits in Kissimmee

Kissimmee, Florida is an enchanting destination filled with diverse attractions, natural beauty, thrilling adventures, and rich history. Whether you’re seeking relaxation, excitement, or a bit of both, you will find it here.

Have we piqued your interest? Consider a stay at one of our cozy and convenient vacation homes or resorts, which provide the perfect home base as you experience Kissimmee.