Kissimmee may be known as the gateway to Walt Disney World, but it’s also a destination in its own right. This vibrant city in Osceola County blends tropical climate, nature preserves, and family fun with easy access to the action in Orlando.
Highlights include:
Spacious house rentals close to top attractions but far from the crowds
Scenic outdoor areas like Shingle Creek Regional Park and Lake Tohopekaliga for kayaking, biking, and wildlife spotting
A relaxed pace with the convenience of nearby shopping, dining, and golf courses
Staying in vacation rentals in Kissimmee means you’re perfectly positioned for both play and peace, with plenty of room to recharge between park-hopping days.
Kissimmee Weather: When Is the Best Time to Visit?
Thanks to its tropical climate, Kissimmee offers warm, sunny weather nearly year-round. Here's what to expect:
Spring (March–May): One of the best times to visit, with sunny skies, lower crowds, and milder temps
Summer (June–August): Peak season for families; hot, humid days are perfect for vacation homes with pools
Fall (September–November): A great time to save money and enjoy the parks with fewer crowds
Winter (December–February): Pleasant temps in the 70s make it ideal for snowbirds and holiday travelers
Whatever the time frame, Wander’s Kissimmee vacation homes make it easy to enjoy the sunshine in style.
Food and Drink in Kissimmee, FL
From lakeside seafood shacks to vibrant Latin cuisine and upscale steakhouses, Kissimmee has something for every craving. Be sure to explore:
- Downtown Kissimmee for local favorites and charming cafés
- Old Town for classic American fare and themed eateries with vintage flair
- The area’s many pet-friendly restaurants and interactive exhibits for kids
- A quick drive to Orlando for world-class dining, wine bars, and foodie experiences
Stock up at nearby markets and enjoy a relaxed dinner in your vacation home in Kissimmee, FL, or hire a private chef to cook for your group.
Points of Interest in Kissimmee
Beyond the parks, Kissimmee offers plenty of local charm and fascinating attractions. Highlights include:
Kissimmee Lakefront Park – Great for walking, biking, or watching the sun set over Lake Toho
Osceola County Welcome Center and History Museum – Learn about the region’s military history and early pioneers
Fun Spot America – A smaller amusement park with go-karts, laser tag, and arcade games
Old Town – A nostalgic walk through retro shops, classic car shows, and old-school rides
Conservation areas for spotting wildlife like bald eagles and alligators
Amazing Activities In & Around Kissimmee
Adventure is never far away when you stay in a Kissimmee vacation home rental. Here’s what you can look forward to:
Day trips to Cocoa Beach (less than an hour’s drive) for sand, surf, and sunshine
Bass fishing tours and airboat rides through the Florida Everglades
Exploring theme park attractions at Universal Studios, SeaWorld, and Walt Disney World
Playing a round on one of the area’s many championship golf courses
Strolling the city center or booking a hot air balloon ride at sunrise
Book Your Kissimmee, FL Vacation Rental with Wander
With premium amenities, unbeatable locations, and room for the whole family, Wander’s Kissimmee house rentals offer a better way to stay.
Skip the cramped hotel room and experience your Florida vacation in style: with a private pool, full kitchen, dedicated workspaces, and all the comforts of home.
Ready to plan your next trip to Kissimmee? Browse our luxury vacation rentals today and create unforgettable memories with Wander.
