Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Popular amenities for Kissimmee vacation rentals
Other great vacation rentals in Kissimmee
Guesthouse in Kissimmee
4.93 out of 5 average rating, 140 reviewsStylish guesthouse close to Disney
Aug. 25 – Sep. 1
Apartment in Kissimmee
4.78 out of 5 average rating, 129 reviews1BR w/Kitchenette near AdventHealth Orlando
Nov. 7 – 14
Home in Davenport
4.95 out of 5 average rating, 58 reviewsSweet vacation home.
May 12 – 19
Townhouse in Kissimmee
5.0 out of 5 average rating, 10 reviewsSummer Studio at Kissimmee
Sep. 8 – 15
Condo in Kissimmee
5.0 out of 5 average rating, 4 reviewsWestgate Vacation Villas 2br suite, Saturday check
Dec. 14 – 21
Tiny homes in Orlando
5.0 out of 5 average rating, 16 reviews3D Printed Micro House - *20 mins EAST of airport*
Aug. 4 – 11
Guesthouse in Kissimmee
4.96 out of 5 average rating, 25 reviewsKissimmee Studio
Jul. 4 – 11
Apartment in Kissimmee
5.0 out of 5 average rating, 8 reviewsBoho Chic Luxury Retreat 5 Min to Parks & Food
Jun. 9 – 16
Quick stats about vacation rentals in Kissimmee
Total rentals
7.3K properties
Rentals with dedicated workspaces
3.6K properties have a dedicated workspace
Rentals with a pool
6.6K properties have a pool
Pet-friendly rentals
1K properties allow pets
Family-friendly rentals
6.3K properties are a good fit for families
Total number of reviews
206K reviews
Your guide to Kissimmee
Welcome to Kissimmee
Located in central Florida, Kissimmee is well situated near some of the most sought-after attractions in the state. Being so close to the Walt Disney World Resort, Universal Orlando Resort, and LEGOLAND Florida parks ensures that this city is popular with families and theme-park fans alike. Kissimmee has its own set of charms to entice visitors, including easy access to the Florida Everglades, the Kennedy Space Center, and many aquatic attractions. You can spend jam-packed days enjoying the company of fairy-tale creatures and riding thrill rides, then change it up with visits to the natural world and dreams of reaching for the stars in outer space. The city has its share of nationally known dining options to cater to visitors from around the world, including entertainment districts that combine the best in food, shopping, and fun. Whether you’re looking for magical lands, family fun, or a wide variety of entertainment options, Kissimmee will deliver an unforgettable holiday experience.
The best time to stay in a vacation rental in Kissimmee
Kissimmee’s busy season runs from March to August, with peak visitation periods taking place during U.S. Thanksgiving, Christmas, and Spring Break (generally March and April). During these times, Orlando’s theme parks are teeming with fans of every age, and the state’s heat and humidity are at their peak. To avoid the worst of the heat, consider booking one of the area’s vacation rentals for between October and March, when temperatures are a bit milder and the crowds have eased up slightly. Pack a light jacket or sweater to wear after the sun sets. The months of July through September are the rainy season in central Florida. Temperatures can often rise above 30 degrees Celsius, and afternoon thundershowers are a common occurrence, so be sure to have protective gear on hand.
Top things to do in Kissimmee
Immerse Yourself in Magical Worlds
Kissimmee is minutes from some of the most popular theme parks in the world. From exploring the four Walt Disney World Resort parks to channeling wizarding magic and superhero power at Universal Orlando Resort and building vacation memories at LEGOLAND Florida, central Florida’s theme parks are not to be missed.
Kennedy Space Center Visitor Complex
Defy gravity and reach for the stars at this gateway to space exploration. The center features behind-the-scenes tours of launch sites and spaceflight facilities, a walk-through rocket garden, astronaut training simulation rides, and the chance to get up close to the Space Shuttle Atlantis.
Florida Everglades
Kissimmee is near Shingle Creek, the headwaters to the Florida Everglades, sometimes called the Sea of Grass. Kayaking in the calm waters beneath a quiet forest of cypress trees is an ideal way to learn more about this unique ecosystem and the many birds, frogs, and alligators who make it their home. Or take a swamp tour on an airboat and leave the driving to someone else.
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