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Villa and house rentals in Kissimmee

Villa and house rentals in Kissimmee

Book self-catered villas, houses, and more on Airbnb

Top-rated villas in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.

Fantasy World Resort Vacation Villa Christmas Week
Entire villa · 6 guests · 4 beds · 2 bathrooms

Fantasy World Resort Vacation Villa Christmas WeekFantasy World is a family friendly vacation resort in Kissimmee Florida offering spacious vacation villas to visiting families at an affordable rate. Located just south of Orlando. Fantasy World Resort is conveniently located just minutes from Orlando FL’s world famous attractions! Scheduled transportation is available to the following attractions: Walt Disney World®, SeaWorld, and Universal Studios Orlando.

Private Luxury Suite/Entrance/Bath 5m to Disney1
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bathroom

Private Luxury Suite/Entrance/Bath 5m to Disney1We are proud to be one of Airbnb's Super Hosts. Our standards are high for you. If you take a moment to read any reviews our guests stay for the service and clean luxury space. Our goal is to welcome you into our home as a family member. We want you to feel at home and have fun, relax and create great memories! Your room has a private entrance, and a Luxurious King Bed. Also, a private in room bathroom, TV with Premium Cable, DVR, refrigerator, premium internet and continental breakfast.

Luxury/5m to Disney/Pool home/ B2
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bathroom

Luxury/5m to Disney/Pool home/ B2Our standards are high. If you take a moment to read any review our guests stay for the service, and clean luxury space. Our goal is not only to provide a clean, comfortable room but to welcome you into our home as a dear family member. We really want you to have a fun and relaxing time and create great memories! Your private room has a Queen luxurious bed. Your shared bath is next to your private room. If no one is in the next room its all yours. TV with cable and free internet. We have 5*+.

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular villa amenities in Kissimmee

  • Pool
  • Hot tub
  • Wifi
  • Air conditioning
  • Kitchen

Houses in Kissimmee

5✯Tranquil ,relax in Jet Tub,LG Suite W/ King bed,
SUPERHOSTPrivate room
5✯Tranquil ,relax in Jet Tub,LG Suite W/ King bed,
Brand new Master bedroom
SUPERHOSTPrivate room
Brand new Master bedroom
Bedroom Near Attractions & Airport
SUPERHOSTPrivate room
Bedroom Near Attractions & Airport
Private, Mediterranean retreat close to Disney!
SUPERHOSTPrivate room
Private, Mediterranean retreat close to Disney!
Romantic Room.....w/in-room bath near Disney Land!
SUPERHOSTPrivate room
Romantic Room.....w/in-room bath near Disney Land!
Magic space Next to MCO Airport
SUPERHOSTEntire house
Magic space Next to MCO Airport
Private room in Kissimmee
SUPERHOSTPrivate room
Private room in Kissimmee
Charming Room Families and Friends
SUPERHOSTPrivate room
Charming Room Families and Friends
30 miles from Disney.  40 miles to Melbourne beach
SUPERHOSTPrivate room
30 miles from Disney. 40 miles to Melbourne beach
Clean, confortable and  Sophisticated place
SUPERHOSTPrivate room
Clean, confortable and Sophisticated place
Just a room. 30 miles to Disney. 40 miles to ocean
SUPERHOSTPrivate room
Just a room. 30 miles to Disney. 40 miles to ocean
Habitación compartida 2 personas 2 camas dobles
Shared room
Habitación compartida 2 personas 2 camas dobles

Pet-friendly villas

Paradise Found Kissimmee Rental
SUPERHOSTEntire villa
Paradise Found Kissimmee Rental
Welcome to your house in Orlando and Disney area!
Entire villa
Welcome to your house in Orlando and Disney area!
Disney Retreat: Private Home w Pool and Game Room
Entire villa
Disney Retreat: Private Home w Pool and Game Room
Lakefront 5 BR 2-Story Villa With Private Pool
SUPERHOSTEntire villa
Lakefront 5 BR 2-Story Villa With Private Pool
7BDR with Movie Theater, Pool/Spa, close to Disney
Entire villa
7BDR with Movie Theater, Pool/Spa, close to Disney
*Renovated Beach House Near Disney w/ Private Pool
Entire villa
*Renovated Beach House Near Disney w/ Private Pool
Mad Men Magic Kingdom House**OUTDOOR MOVIE EXPERIENCE*FREE Heated Pool&Spa&Grill*6mi2Disney*WORK SPACE
SUPERHOSTEntire villa
Mad Men Magic Kingdom House**OUTDOOR MOVIE EXPERIENCE*FREE Heated Pool&Spa&Grill*6mi2Disney*WORK SPACE
Amazing, Cozy 4BR/3B. This house was made for YOU!
SUPERHOSTEntire villa
Amazing, Cozy 4BR/3B. This house was made for YOU!
1816 Home on the Road
SUPERHOSTEntire villa
1816 Home on the Road
Westgate Lake Resort 2 BDRMS deluxe
Entire villa
Westgate Lake Resort 2 BDRMS deluxe
*Just Renovated* Amazing 3BR Villa w/ Free Hot Tub
Entire villa
*Just Renovated* Amazing 3BR Villa w/ Free Hot Tub
Solara Dream - 9 Bedroom Villa (Up to 30 Guests)
SUPERHOSTEntire villa
Solara Dream - 9 Bedroom Villa (Up to 30 Guests)

Villas with pools

***Paradise Island Cove 4/3 Pool close theme parks
Entire villa
***Paradise Island Cove 4/3 Pool close theme parks
The Dorset Shire
Entire villa
The Dorset Shire
Sandy Ridge Villa, Large South Facing Pool & Spa
SUPERHOSTEntire villa
Sandy Ridge Villa, Large South Facing Pool & Spa
Large villa situated in Orlando's finest suburb
Entire villa
Large villa situated in Orlando's finest suburb
Doorway to Disney
SUPERHOSTEntire villa
Doorway to Disney
Vistana-Sheraton Resort-Orlando, Nr. Disney
Entire villa
Vistana-Sheraton Resort-Orlando, Nr. Disney
🌞 2 master suites! Venetian Bay Villages! VEJA!!🌴
SUPERHOSTEntire villa
🌞 2 master suites! Venetian Bay Villages! VEJA!!🌴
Destiny Disney
SUPERHOSTEntire villa
Destiny Disney
Luxury villa, private pool, near Disney,WiFi
Entire villa
Luxury villa, private pool, near Disney,WiFi
Disney Area Luxury Villa with Pool
SUPERHOSTEntire villa
Disney Area Luxury Villa with Pool
Star Island Resort deluxe family suite
Entire villa
Star Island Resort deluxe family suite
Casa near Disney: 5 bed/3 bath lakefront pool home
Entire villa
Casa near Disney: 5 bed/3 bath lakefront pool home

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.

Getting There

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.

Weather

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.

Don't Miss

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.

Nearby destinations