Skip to content
Some content has been automatically translated. Show original language

Vacation rentals in Kissimmee

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Kissimmee

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

SUPERHOST
  1. Entire villa
  2. Davenport
Sandy Ridge Villa, Large South Facing Pool & Spa

Superbly situated at the end of a small cul-de-sac with no rear neighbours and conservation views. Our 5 bedroomed villa sleeps a maximum of 10 people. Fully air conditioned. Large south facing pool and spa with sun loungers completely screened. Pool and spa heating at extra cost. Complimentary high speed wireless internet and cable TV in all bedrooms. The garage has been converted to a games room which has a pool table, air hockey table, bar football, table tennis and a dartboard.

$119 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Cozy Suite at Compass Bay Resort

Relax in this beautiful and charming suite nicely decorated with a full bathroom inside. We are located near all major restaurants and shops.

$41 per night
  1. Private room
  2. Kissimmee
Single Private Bedroom with a Queen Bed (Room 3)

Relax with the whole family at this peaceful place to stay.

$32 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Villas
  • Resorts

Houses in Kissimmee

SUPERHOST
  1. Entire home
  2. Kissimmee
Beautiful Bright And Cozy 3•Bedroom🏡 Lovely Home
$124 per night
  1. Entire home
  2. Kissimmee
100% renewed 4-bedroom house w/ private pool and spa
$164 per night
  1. Entire home
  2. Kissimmee
Disney vacation home rental.
$129 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
3 bedroom Orlando Florida pool home
$106 per night
  1. Entire home
  2. Kissimmee
Beautiful Clean & Quiet Disney Vacation Home Rent!
$169 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Nice one private Bedroom and Bathroom
$25 per night
  1. Entire home
  2. Kissimmee
Lakeview 6BR Pool/SPA Home, Right beside Clubhouse
$241 per night
  1. Private room
  2. Kissimmee
2 Koala Kozy Korner In Kissimmee
$25 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
South Facing Pool Home! 5 Miles from Disney
$148 per night
  1. Private room
  2. Orlando
Cheerful and Cosy master bedroom
$49 per night
  1. Entire home
  2. Kissimmee
SPACIOUS 3 Bedrooms/2 Bathrooms HOME! PRIVATE POOL
$133 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Villa near Disney with heated pool
$115 per night

Condo rentals in Kissimmee

SUPERHOST
  1. Private room
  2. Kissimmee
Quaint condo close to Disney and Universal.
$35 per night
  1. Private room
  2. Kissimmee
room in kissimme 15-20 minutes from the parks
$39 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
Incredible Family Fun at Calypso Cay - 1 BR
$61 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
RESORT (02) NEAR DISNEY PARKS
$65 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
Calypso Cay Vacation Villas 2BR Suite, SATURDAY Check-In
$75 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
*Resort complex*Next to parks*
$126 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
Calypso Cay Vacation Villas 1BR Suite, SATURDAY Check-In
$65 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
Mickey Mouse Themed Getaway next to Disney 1
$99 per night
  1. Entire condo
  2. Kissimmee
Bright, stylish 3BR 2BA condo near all parks
$102 per night
  1. Entire condo
  2. Ventura
Peaceful, full-featured condo near airport & parks
$42 per night
  1. Entire condo
  2. Kissimmee
Lovely 3BR 2BA condo, great amenities and location
$108 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
2BD/2BA Brand New condo near Disney #120
$135 per night

Weekly rentals in Kissimmee

  1. Entire home
  2. Kissimmee
BELLA VIDA 4515MD - 4 BEDROOMS - 3 BATH - 8 GUESTS
$183 per night
  1. Entire home
  2. Kissimmee
Private pool villa near Disney (games room)
$102 per night
SUPERHOST
  1. Entire home
  2. Davenport
Sunnyside Villa Near Disney Private Pool 8 guests
$104 per night
  1. Entire home
  2. Davenport
Perfect FAMILY VILLA 5BR w/ Pool NO REAR NEIGHBOR
$131 per night
  1. Entire home
  2. Kissimmee
Cheerful 4-Bed 3-bath residential home with pool!
$169 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Disney Vacation Home
$150 per night
  1. Entire home
  2. Kissimmee
☀️Cozy 4BR Town Home with POOL Close to Disney!
$165 per night
  1. Entire home
  2. Kissimmee
Disney Area 3 bedroom 2 bath with Heated Pool 3129
$152 per night
  1. Entire home
  2. Kissimmee
✨Ultimate 6BR Villa Disney Getaway! WITH SPA!
$209 per night
  1. Entire home
  2. Kissimmee
6BR Family Villa w/ private POOL/SPA near Disney
$244 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Private Heated Pool! Relax, Unwind and Enjoy!
$163 per night
  1. Entire home
  2. Kissimmee
GREEN-VIEW 6BR Villa w/Pool/SPA, close to Disney
$195 per night

Your guide to Kissimmee

All About Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.


How do I get around Kissimmee?

Kissimmee is a 25-minute drive from its closest travel hub, the Orlando International Airport (MCO). From the airport, travelers can take the bus and connect to central Florida’s Sunrail to get to Kissimmee. Taxis, ride-hailing services, and car rental options are available at the airport as well. Once you’re in the central Kissimmee area, the bus and tram routes might not reach every place you plan to go to, but taxis and ride-hailing services are handy replacements. For any travel outside of Kissimmee, a rental car will be essential.


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

Kissimmee weather stays fairly warm throughout the year, but visitors should plan for a few rainy days here and there. Summers are usually hot and humid, and on a sunny day, a visit to Cocoa Beach is about an hour’s drive away from most Kissimmee vacation rentals. Spring weather is cooler but warm enough to kayak through the headwaters of the Florida Everglades at the Shingle Creek Regional Park. On a typical winter or fall day, the weather is cool and comfortable enough to be outdoors. During these two seasons, you can plan a picnic at the serene Brownie Wise Park facing Kissimmee’s massive Lake Tohopekaliga.


What are the top things to do in Kissimmee?

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.