Villa and house rentals in Kissimmee

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Top-rated villas in Kissimmee

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Beautiful Modern Villa near Disney #03321
Entire villa · 4 guests · 2 beds · 1 bathroom
Beautiful Modern Villa near Disney #03321Relax and enjoy this 1 bedroom/1 bathroom modern villa with a separate sitting area and small kitchenette. It will sleep 2 to 4 guest and is minutes from Disney and other attractions.
Blessed 3-Bedroom Villa
Entire villa · 6 guests · 4 beds · 2 bathrooms
Blessed 3-Bedroom VillaRelax with the whole family at this peaceful place to stay. Enjoy your stay and explore Disney World and other Parks just minutes away. Walmart,Target, and many Restaurants in the area.
Free Pool Heat!Close to Disney.Luxury House
Entire villa · 12 guests · 7 beds · 5 bathrooms
Free Pool Heat!Close to Disney.Luxury HouseWhat's better than relaxing at our spacious & modern villa after a long day hanging out with Mickey Mouse at Disney or shopping at premium outlets? Our villa, located in the newly built Storey Lake resort, offers 2 large gathering places for everyone in your party. You're only 4 minute walk to the clubhouse with all the amazing amenities: sports court, Jacuzzi, lazy river, pools, cabanas, poolside food and beverage service, playgrounds and Splash Park. Free Pool Heat for Jan/Feb of 2022

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Stay near Kissimmee's top sights

Medieval Times Dinner & Tournament
Theme Restaurant · 105 locals recommend
Photo of Medieval Times Dinner & Tournament

Travel through the mists of time to a forgotten age and a tale of devotion, courage and love—at Medieval Times Dinner & Tournament. Imagine the pageantry and excitement that would have been yours as a guest of the king ten centuries ago...

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    4420 - Le Reve · 20LR New house! 4 bedroom , Excellent location
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    New Renovated 3/2 Home Lake resort close to Disney
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    Disney Getaway | Lake Berkley Resort | Pool | 6ppl
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    Lake Townhome w/private pool close to theme parks
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    King Bed Pool Condo 20 Min To Disney W/Pet Care
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    Quaint condo close to Disney and Universal.
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    1204 AWESOME LOCATION BRAND NEW PRIVATE POOL
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    ♫♪Let it Go♫♪ - The Force is Strong With This One | Private Heated Pool | 2 Masters! - Pool Heat and BBQ/Propane included!
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    The Best Luxury Apartment near Disney
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    Sanitized⭐ King bedroom🌟 Executive apartment
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    Large Luxury Apt-Great Location 1 Bedroom-2 Beds
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    Cozy luxurious 1 bedroom King with Air Sanitizer!!

Your guide to Kissimmee

All About Kissimmee

Located in the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.


How do I get around Kissimmee?

Orlando International Airport (MCO) is just 16 miles northeast of Kissimmee and is served by most major airlines, making it the easiest way to get here. Even closer, Kissimmee Gateway Airport (ISM) is only two miles away but doesn’t offer scheduled flights — if you’re flying in on a private or chartered jet, this is likely where you’ll land. For road-trippers from other Florida cities, Kissimmee is an easy drive: it’s four hours from Tallahassee, about three hours from both Miami and Jacksonville, and under two hours from Tampa. Visitors from Georgia, South Carolina, Alabama, and even North Carolina may also opt to make the day’s drive rather than flying in.

Rideshare options and public transportation are plentiful here, but many visitors prefer to rent a car to visit nearby theme parks or to more easily drive out into the Osceola County countryside. Find rental locations at Orlando Airport and in downtown Kissimmee.


When is the best time to stay in a vacation rental in Kissimmee?

The weather in central Florida is nice year-round — there’s a reason it’s called the Sunshine State. Winters in Kissimmee tend to be sunny, warm, and dry, so around the holidays, Florida tends to be a popular escape for those who live in colder climates. Though temperatures hover around 70 degrees Fahrenheit from December through February, you’ll still want to pack a jacket. In the busy summer months, you can expect temperatures around 90 degrees and the kind of humidity that makes air conditioning a necessity. Keep in mind that summer and early autumn also bring hurricanes to Florida. Spring and fall can be considered the best of both worlds, with lovely weather and fewer crowds.


What are the top things to do in Kissimmee?

Old Town

Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.

Fan Boat Swamp Tour

Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.

Hot Air Balloon Ride

Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.