Vacation rentals in Kissimmee

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Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Give Kids The World Village7 locals recommend
Walmart Supercenter44 locals recommend
Medieval Times Dinner & Tournament346 locals recommend
Osceola Heritage Park12 locals recommend

Quick stats about vacation rentals in Kissimmee

  • Total rentals

    7.2K properties

  • Total number of reviews

    217K reviews

  • Family-friendly rentals

    6.2K properties are a good fit for families

  • Pet-friendly rentals

    1.1K properties allow pets

  • Rentals with a pool

    6.5K properties have a pool

  • Rentals with dedicated workspaces

    3.9K properties have a dedicated workspace

Your guide to Kissimmee

All About Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.

The best time to stay in a vacation rental in Kissimmee

Kissimmee weather stays fairly warm throughout the year, but visitors should plan for a few rainy days here and there. Summers are usually hot and humid, and on a sunny day, a visit to Cocoa Beach is about an hour’s drive away from most Kissimmee vacation rentals. Spring weather is cooler but warm enough to kayak through the headwaters of the Florida Everglades at the Shingle Creek Regional Park. On a typical winter or fall day, the weather is cool and comfortable enough to be outdoors. During these two seasons, you can plan a picnic at the serene Brownie Wise Park facing Kissimmee’s massive Lake Tohopekaliga.

Top things to do in Kissimmee

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.

Frequently Asked Questions

  • How is the weather in Kissimmee?

    Kissimmee boasts a tropical climate, with hot, humid summers reaching 90°F (32°C) and milder winters averaging around 60°F (15°C). Rainfall is more frequent in the summer, while winter tends to be drier.

  • What are some of the best things to do in Kissimmee?

    Popular activities in Kissimmee include exploring the Old Town, a recreated Florida town full of shops and restaurants, taking a thrilling airboat tour on Lake Tohopekaliga, or enjoying a round of golf at one of the city's many golf courses.

  • What is the best time of year to visit Kissimmee?

    The most popular time to visit Kissimmee is in the summer, particularly between March and August. During this period, the city hosts local events such as the Kissimmee Sunshine Regional Chili Cook-Off and the Silver Spurs Rodeo.

  • What are the best places to stay in Kissimmee?

    Celebrate, a family-friendly community, is often recommended for its proximity to theme parks. Downtown Kissimmee is popular for its vibrant nightlife and historic landmarks. West Kissimmee, located close to a number of natural attractions, is also frequently suggested.

  • What are the best places to visit in Kissimmee?

    Popular places to visit in Kissimmee include the Kissimmee Lakefront Park, the Osceola County Historical Society Pioneer Village, and Gatorland, a wildlife preserve and theme park.

  • What are some hiking trails in Kissimmee?

    Kissimmee has a variety of hiking trails such as the Shingle Creek Regional Trail for scenic views of natural Florida or the Disney Wilderness Preserve which is home to numerous species of plants and animals.

  • What are some family activities to do in Kissimmee?

    Families in Kissimmee can explore numerous attractions including the interactive exhibits at the Museum of Military History, a fun-filled day at Fun Spot America amusement park, or a chance to spot native Florida wildlife at the Wildlife Refuge.

  • What are some of the best day trip ideas in Kissimmee?

    Popular day trips from Kissimmee often include a visit to Orlando, just 17 miles (27 km) away, to experience its world-renowned theme parks. Alternatively, the beautiful beaches of Clearwater are just 90 miles (145 km) away.

  • Are there vacation rentals with a dedicated workspace in Kissimmee?

    Yes! Work meets play with ease at over 3,870 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Kissimmee?

    Four-legged friends are welcome in Kissimmee. Choose from more than 1,080 vacation rentals for guests traveling with pets.

Destinations to explore

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  3. Florida
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