Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Popular amenities for Kissimmee vacation rentals
Homes for rent in Kissimmee
Home in Kissimmee
4.81 out of 5 average rating, 108 reviewsBeautiful Vacation Home With Private Pool.
Home in Kissimmee
4.86 out of 5 average rating, 176 reviewsPersonal pool home 4/2close to Disney!
Home in Kissimmee
4.86 out of 5 average rating, 174 reviewsCharming 3-Bedroom Home: 25 Mins from Disney!
Home in Kissimmee
4.83 out of 5 average rating, 143 reviewsNice house, private community, with pool
Home in Kissimmee
4.87 out of 5 average rating, 302 reviewsBe Our Guest !
Home in Kissimmee
4.9 out of 5 average rating, 105 reviewsTropical Lagoon at Runaway Beach Club *Disney*
Home in Kissimmee
4.81 out of 5 average rating, 112 reviewsPool House in Kissimmee
Home in St. Cloud
4.98 out of 5 average rating, 172 reviewsCozy Spacious studio with private entrace.
Apartments for rent in Kissimmee
Rental unit in Winter Garden
4.97 out of 5 average rating, 236 reviewsLakeview Garden Studio
Rental unit in Kissimmee
4.89 out of 5 average rating, 314 reviews3BR/2Bath Spacious condo 15min Disney
Rental unit in Florida Center
4.88 out of 5 average rating, 282 reviewsCarmen Romantic Studio W/Private Beautiful Terrace
Rental unit in Kissimmee
4.95 out of 5 average rating, 154 reviewsLovely one bedroom apartment.
Rental unit in Clermont
4.82 out of 5 average rating, 243 reviewsCharming Lakefront Apt. Near Disney
Rental unit in Winter Garden
4.9 out of 5 average rating, 126 reviewsStay A While
Rental unit in Kissimmee
4.87 out of 5 average rating, 210 reviewsModern Great Villa near Disney & Parks
Rental unit in Kissimmee
4.9 out of 5 average rating, 127 reviewsLuxury 2/2 Condo, close to Disney/Free Water Park
Villas for rent in Kissimmee
Villa in Kissimmee
4.85 out of 5 average rating, 113 reviewsModern Pool Villa, Game Room & Theater Near Disney
Villa in Kissimmee
4.97 out of 5 average rating, 145 reviewsClose To The Mouse: Something for Everyone!
Villa in Kissimmee
4.85 out of 5 average rating, 389 reviewsDisney Area w/ Movie Theater, Game Room and Pool!
Villa in Kissimmee
4.91 out of 5 average rating, 139 reviewsLuxury villa Salt Pool&Spa close to Disney
Villa in Kissimmee
4.88 out of 5 average rating, 108 reviewsNEW Unique 6BR,private pool,Full game room, + MORE
Villa in Kissimmee
4.85 out of 5 average rating, 158 reviewsAmazing House close to Disney. Enjoy Private Pool!
Villa in Kissimmee
4.9 out of 5 average rating, 101 reviewsBeautiful Home with Pool near Golf & Disney
Villa in Kissimmee
4.8 out of 5 average rating, 174 reviewsKing bed pool free parking resort 15 min disney
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.
What types of vacation rentals are available in Kissimmee?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Kissimmee. From over 800 villa rentals, over 3,390 house rentals to over 480 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
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.
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