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Vacation rentals in Kissimmee

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Top-rated vacation rentals in Kissimmee

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

SUPERHOST
  1. Entire condo
  2. Kissimmee
RESORT (02) NEAR DISNEY PARKS

Single apartment with all amenities, in excellent location, near DISNEY Parks, and many restaurants and shops, with access to major communication roads in the city

G$13,608 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
South Facing Pool Home! 5 Miles from Disney

Beautiful South Facing Pool Home! 5 Miles from Disney

G$29,728 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.

G$8,435 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Houses in Kissimmee

SUPERHOST
  1. Entire home
  2. Kissimmee
Beautiful Bright And Cozy 3•Bedroom🏡 Lovely Home
G$25,870 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Great home near Disney World for affordable rentals
G$22,599 per night
  1. Private room
  2. Kissimmee
Single Private Bedroom with a Queen Bed (Room 3)
G$6,519 per night
  1. Entire home
  2. Kissimmee
Private pool villa near Disney (games room)
G$21,354 per night
  1. Entire home
  2. Kissimmee
Mickey's Crib, Kissimmee The Heart of Disney
G$21,383 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
7-bedroom vacation home near Disney with pool/spa
G$38,730 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Family Home minutes from Disney!
G$21,982 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Fantastic 7BR/4.5B, Private Pool/SPA, Disney Area!
G$52,637 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
3 bedroom Orlando Florida pool home
G$22,729 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Home near Disney 4br with pool
G$30,984 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
3 bedroom Villa in Kissimmee
G$18,842 per night
SUPERHOST
  1. Private room
  2. Saint Cloud
30 miles from Disney. 40 miles to Melbourne beach
G$5,923 per night

Weekly rentals in Kissimmee

SUPERHOST
  1. Entire home
  2. Kissimmee
4926 - Brand New Modern Home w/ Splash Pool
G$32,563 per night
  1. Entire home
  2. Kissimmee
SPACIOUS 3 Bedrooms/2 Bathrooms HOME! PRIVATE POOL
G$26,678 per night
  1. Entire home
  2. Kissimmee
BELLA VIDA 4515MD - 4 BEDROOMS - 3 BATH - 8 GUESTS
G$35,979 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Beautiful pond view 3-bedroom home with a pool
G$28,562 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Disney Vacation Home
G$31,403 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Welcome to your house in Orlando and Disney area!
G$35,142 per night
  1. Entire home
  2. Kissimmee
3 Bed/2.5 bath So beautiful You`ll get Goose Bumps
G$40,076 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Private Heated Pool w/ View! Soothing Tranquility!
G$41,870 per night
SUPERHOST
  1. Private room
  2. Kissimmee
Beautiful In-law suite in amazing location!
G$11,395 per night
  1. Entire home
  2. Kissimmee
Disney area 3 Bed 2 Bath-HEATED Pool 5371
G$27,574 per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Modern 4 Bedroom House with Pool & Jacuzzi
G$50,902 per night
  1. Entire home
  2. Kissimmee
Disney Magical Memories Vacation Home
G$41,870 per night

Weekly rentals in Kissimmee

SUPERHOST
  1. Entire condo
  2. Kissimmee
Calypso Cay Vacation Villas 1BR Suite, SATURDAY Check-In
G$13,608 per night
  1. Entire condo
  2. Kissimmee
Affordable and so close to Disney
G$14,655 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
Adventure Awaits at Calypso Cay - 2 Bedroom Condo!
G$21,228 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
Mickey Mouse Themed Getaway next to Disney 1
G$20,726 per night
SUPERHOST
  1. Entire condo
  2. Orlando
Grand Beach Resort 3BR Suite, SATURDAY Check-In
G$16,748 per night
  1. Private room
  2. Kissimmee
room in kissimme 15-20 minutes from the parks
G$8,016 per night
  1. Entire condo
  2. Orlando
World Quest Orlando Resort 3BR 2BA
G$16,748 per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
*NEW*• Modern Luxury Condo
G$24,643 per night
  1. Entire condo
  2. Orlando
Balcony w/Pool View-Disney area-2 Bed/2 Bath Condo
G$27,335 per night
  1. Entire condo
  2. Kissimmee
Storey Lake 3 BR, CLOSE TO DISNEY. NO RESORT FEES!
G$29,728 per night
  1. Entire condo
  2. Kissimmee
Funshine even in the rain.
G$19,888 per night
SUPERHOST
  1. Entire condo
  2. Orlando
Grand Beach Resort 3BR Suite, SATURDAY Check-In
G$19,888 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.