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Vacation rental houses in Kissimmee

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Top-rated houses in Kissimmee

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

Great home near Disney World for affordable rentals
SUPERHOST
Entire residential home · 6 guests · 6 beds · 2.5 baths
Great home near Disney World for affordable rentalsThe house is in a closed area. Very nice place, 100 meters from the pool, garden, tennis court and gym. The house is 130 sqm spread over 2 floors. 3 bedrooms and 2 1/2 bathrooms. Bright and pleasantly furnished.
4 BR South Facing Pool Home 5 miles from Disney
SUPERHOST
Entire residential home · 8 guests · 6 beds · 2.5 baths
4 BR South Facing Pool Home 5 miles from DisneyThis beautiful 4 bedroom home is located just minutes from Disney World, Sea World, Universal Studios, and other Orlando attractions. The home includes a private heated south facing swimming pool with a 51 jet Hot Tub. We offer free High Speed Wireless internet and Cable TV. Free Pool and Spa Heat, Gas Grill, and no Charge for Cleaning. This property is privately owned and has 24-hour on call management and is spotless, with professional care for the pool and lawn every week.
5 Bedrooms/5 Bathrooms Storey Lake (4777 KC)
Entire residential home · 14 guests · 10 beds · 5 baths
5 Bedrooms/5 Bathrooms Storey Lake (4777 KC)5 Bedroom/5 Bathroom Storey Lake (4777KC)

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Townhouses
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Popular house amenities in Kissimmee

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

Townhouses in Kissimmee

  1. Private room
  2. Kissimmee
Clean, confortable and Sophisticated place
$41 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
Disney World Vacation Home - The Mouse Townhouse #3
$108 per night
  1. Entire townhouse
  2. Kissimmee
Fantasy World 2br, Luxury on Wet n Wild #5
$100 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
Disney World Vacation Home - The Mouse Townhouse #2
$108 per night
SUPERHOST
  1. Private room
  2. Kissimmee
QUIET AND CLEAN BEDROOM NEAR DISNEY AND PARKS!!
$39 per night
  1. Entire townhouse
  2. Kissimmee
Family Fun
$123 per night
SUPERHOST
  1. Private room
  2. Kissimmee
CLEAN AND QUIET BEDROOM,NEAR DISNEY!
$40 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Private Bedroom, 8 Minutes to Disney Main Gate #1
$62 per night
  1. Private room
  2. Kissimmee
Mickey Room #1 For your Vacation With Private Bath
$39 per night
  1. Private room
  2. Kissimmee
80-Paradise 10 min Disney Queen private bath
$40 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Private Room Queen #1 hosted by Isac&Miriam
$32 per night
SUPERHOST
  1. Private room
  2. Kissimmee
♕ King Suite 1. Close to Everything
$41 per night

Pet-friendly houses

  1. Entire residential home
  2. Kissimmee
3 Bed/2.5 bath So beautiful You`ll get Goose Bumps
$179 per night
  1. Entire residential home
  2. Kissimmee
Cozy Family Home up to 9 & Pool/BBQ - Near Disney
$110 per night
  1. Entire residential home
  2. Kissimmee
Near Disney w/ private pool renovated villa
$138 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Exquisite Destination Villas
$120 per night
  1. Entire residential home
  2. Kissimmee
5BR Luxury Home - Family Resort - Private Pool, Hot Tub and BBQ!
$150 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
4 Bedrooms/2 Bathrooms AMAZING HOME! PRIVATE POOL!
$156 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Cool Summer. Lakeside Kissimmee 25 min from Disney
$156 per night
  1. Entire residential home
  2. Kissimmee
Pool house 3rooms+office near theme park
$113 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
6BR Family Resort Mansion Private Pool/BBQ/More!
$271 per night
  1. Entire residential home
  2. Kissimmee
Modern Villa only 20min drive to major themeparks
$120 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Private4BRhome,PrvtPool,FencedYard,GameRM,WiFi
$151 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
4BR.Sanitized.Private Pool-HBO-WiFi-Gated Resort
$128 per night

Houses with pools

  1. Entire residential home
  2. Kissimmee
Modern 4 Bedroom House with Pool & Jacuzzi
$145 per night
  1. Private room
  2. Kissimmee
BEAUTIFUL PRIVATE BEDROOM NEAR DISNEY
$35 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Centrally located Kissimmee Vacation Home
$62 per night
  1. Entire residential home
  2. Kissimmee
5BD/5BA PRIVATE POOL! SONOMA RESORT (2673CA)
$105 per night
  1. Private room
  2. Kissimmee
Beautiful In-law suite in amazing location!
$55 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Fantasy World Renovated 2BR, Close to Disney.
$106 per night
  1. Entire residential home
  2. Kissimmee
Disney Vacation Home
$150 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Private Room in Orlando/Kissimmee (King 2)
$40 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Family Home minutes from Disney!
$95 per night
  1. Entire residential home
  2. Kissimmee
BELLA VIDA 4515MD - 4 BEDROOMS - 3 BATH - 8 GUESTS
$149 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
♥ Spacious Water View w/Pool °o° Disney Area☆No Carpet☆
$120 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Cheerful 4-BR New home minutes away from Disney
$146 per night

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.