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Vacation rental houses in Kissimmee

Book unique vacation rental houses, apartments, and more on Airbnb

Top-rated houses in Kissimmee

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

Recently Renovated 5 BR Home With Private Pool
Entire residential home · 12 guests · 8 beds · 3 baths
Recently Renovated 5 BR Home With Private PoolBring the whole family to this great place located in a prestigious resort with lots of room for fun and a private pool.
NO AIRBNB FEES!! Entire Thematic House!! Private Pool and Jacuzzi!!! Thematic Game Room!!
Disney only 11 miles away!! More houses is profile!
SUPERHOST
Entire residential home · 12 guests · 8 beds · 4 baths
NO AIRBNB FEES!! Entire Thematic House!! Private Pool and Jacuzzi!!! Thematic Game Room!! Disney only 11 miles away!! More houses is profile!Fully furnished, 5 bedroom thematic vacation home! Tucked away in a quiet residential community, you will find this gem. 5 thematic bedroom, including a thematic game room equipped with arcade style games, ping pong table, air hockey, and foosball! The house also has a private pool with hot tub (heating at an additional cost). Located just 11 miles from Disney!! Also close to many other attractions and local restaurants. Need a place to relax with family, well look no further!
The Red Door House Disney Area / Private Room+Bath
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath
The Red Door House Disney Area / Private Room+BathHalf-way in between Disney and Universal area. Guest room in a charming house in one of the best areas of Orlando. Situated on a cul-de-sac within a friendly safe suburbia, the street/home is quiet. Clean, peaceful setting, relaxed home. 30 min to Disney. 20 min to Sea World. 2 guests max per room. * Private bath with tub/shower combo * WIFI/ TV / ROKU * Small refrigerator in room * Coffee maker in room * Safe driveway parking * Comfortable bed

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Townhouses
  • Villas

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
$40 per night
PLUS
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  2. Kissimmee
Find a Little Magic in a Townhouse near Disney and Universal
$156 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Cozy Suite at Compass Bay Resort
$37 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
Disney World Vacation Home - The Mouse Townhouse #3
$108 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
Stylish Lake Townhome w/private pool at Bella Vida
$132 per night
  1. Entire townhouse
  2. Kissimmee
Free Waterpark - Fantasy World 2br - Rosie
$94 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
Disney World Vacation Home - The Mouse Townhouse #2
$108 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
1206 BRAND NEW AT A GREAT LOCATION NEAR DISNEY
$141 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
Luxury Remodeled Townhome minutes from Disney!
$148 per night
SUPERHOST
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  2. Kissimmee
RUSTY'S DEN House with Hot Tub 3 miles from Disney
$127 per night
SUPERHOST
  1. Entire townhouse
  2. Kissimmee
MY HAPPY PLACE ONE!! ✓ 5 minutes to DISNEY
$95 per night
  1. Entire townhouse
  2. Kissimmee
Sanitized Cozy 4Bed Brand New Home - Jacuzzi&Pool
$149 per night

Pet-friendly houses

SUPERHOST
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3BR-CLEAN-Jacuzzi-HBO,WiFi,BBQ,HeatedRESORTpool
$115 per night
SUPERHOST
  1. Entire residential home
  2. Osceola County
4 Bedroom / 3 Bathroom - Compass Bay (5149)
$95 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Hidden Gem-Cozy Home Gated Community Pet Friendly
$130 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Entire House with Pool and jacuzzi near Disney!!!!
$201 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
4 Bedrooms/2 Bathrooms AMAZING HOME! PRIVATE POOL!
$156 per night
  1. Entire residential home
  2. Kissimmee
Near Disney w/ private pool renovated villa
$142 per night
  1. Entire residential home
  2. Kissimmee
5BR Luxury Home - Family Resort - Private Pool, Hot Tub and BBQ!
$154 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Hideaway Home By The LAKE At The Storey Lake.
$232 per night
  1. Entire residential home
  2. Kissimmee
Newly renovated Luxe home minutes from Disney
$165 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Exquisite Destination Villas
$120 per night
  1. Entire residential home
  2. Kissimmee
Charming Luxury Home 7 BR, 6 Bath, Pool & Jacuzzi
$199 per night
SUPERHOST
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  2. Kissimmee
Casa Feliz - Your 2nd Large Home
$195 per night

Houses with pools

SUPERHOST
  1. Private room
  2. Kissimmee
Bedroom, private bath in mansion style near Disney
$56 per night
  1. Entire residential home
  2. Kissimmee
Magical Cove Disney Themed Townhome Kissimmee FL
$115 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Complete Renovated 5Br Modern Terra Verde Resort
$209 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
***BIG DISNEY FAMILY HOME*** PRIVATE POOL- 5 Bed
$162 per night
  1. Entire residential home
  2. Kissimmee
3 Bedrooms/2 Bath Venetian Bay Village Cozy Town
$86 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
10 min to Disney, Resort Style Brand new home
$159 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Charming Villa with Pool!! Just past the 7 dwarfs
$150 per night
  1. Entire residential home
  2. Kissimmee
Modern 4 Bedroom House with Pool & Jacuzzi
$169 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Cheerful 4-BR New home minutes away from Disney
$160 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
4B New Home/Pool/Wifi/10Min Disney
$159 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
3 Bedroom / 2 Bathroom - Seven Dwarfs Lane (2608)
$85 per night
SUPERHOST
  1. Entire residential home
  2. Kissimmee
Upscale Contemporary Waterfront 3/2 Heated Pool
$225 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.