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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.

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  1. Entire condo
  2. Kissimmee
Incredible Family Fun at Calypso Cay - 1 BR

Calypso Cay Resort is a family-friendly, Caribbean-themed Kissimmee property and is located famous for…Walt Disney World® Resort, Universal Studios® and Sea World®. The awesome amenities at Calypso Cay Resort include: 18 holes of mini golf, 3 outdoor heated pools, 2 are zero entry, 2 hot tubs, 3 water slides, License To Chill Tiki Bar & Grill, sand volleyball, lighted basketball, family grilling areas and covered cabanas, Dunkin’ Donuts, fitness room, game room, FREE WIFI and parking.

R1,006 ZAR per night
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

R1,623 ZAR 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.

R527 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Kissimmee's top sights

Photo of Kissimmee Lakefront Park
Kissimmee Lakefront Park38 locals recommend
Photo of Skate Reflections
Skate Reflections3 locals recommend
Photo of Medieval Times Dinner & Tournament
Medieval Times Dinner & Tournament98 locals recommend
Photo of Give Kids The World Village
Give Kids The World Village3 locals recommend
Photo of Silver Spurs Arena
Silver Spurs Arena3 locals recommend
Photo of Osceola Heritage Park
Osceola Heritage Park5 locals recommend

Houses in Kissimmee

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  2. Kissimmee
Lovely Luxury 3-Bedroom Full House
R1,272 ZAR per night
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  1. Entire home
  2. Kissimmee
NEW LISTING: Heated Pool 15 Minutes to Disney
R4,120 ZAR per night
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  1. Entire home
  2. Kissimmee
3 bedroom Orlando Florida pool home
R1,640 ZAR per night
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  1. Entire home
  2. Kissimmee
South Facing Pool Home! 5 Miles from Disney
R2,649 ZAR per night
  1. Entire home
  2. Kissimmee
Beautiful Bright And Cozy 3•Bedroom🏡 Lovely Home
R2,354 ZAR per night
SUPERHOST
  1. Private room
  2. St. Cloud
Just a room. 30 miles to Disney. 40 miles to ocean
R457 ZAR per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Private Heated Pool! Relax, Unwind and Enjoy!
R2,607 ZAR per night
  1. Private room
  2. Kissimmee
Very convenient place near Disney and airport
R607 ZAR per night
  1. Entire home
  2. Kissimmee
BELLA VIDA 4575- 5 BEDROOMS - 12 GUESTS- GAME ROOM
R3,872 ZAR per night
  1. Entire home
  2. Kissimmee
SANITIZED Storey Lake, Free Warterpark NC207
R2,132 ZAR per night
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  1. Entire home
  2. Kissimmee
Recently Renovated 5 BR Home With Private Pool
R3,392 ZAR per night
  1. Entire home
  2. Kissimmee
Mickey's Crib, Kissimmee The Heart of Disney
R1,804 ZAR per night

Condo rentals in Kissimmee

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  1. Entire condo
  2. Kissimmee
Mickey Mouse Themed Getaway next to Disney 1
R1,623 ZAR per night
SUPERHOST
  1. Private room
  2. Kissimmee
Quaint condo close to Disney and Universal.
R736 ZAR per night
  1. Entire condo
  2. Kissimmee
Storey Lake 3 BR, CLOSE TO DISNEY. NO RESORT FEES!
R2,586 ZAR per night
  1. Entire condo
  2. Kissimmee
Astonishing 2BR brand new condo/full resort access
R1,668 ZAR per night
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  1. Entire condo
  2. Kissimmee
Adventure Awaits at Calypso Cay - 2 Bedroom Condo!
R1,663 ZAR per night
SUPERHOST
  1. Entire condo
  2. Kissimmee
2BD/2BA condo close to Disney at Storey Lake #91
R2,377 ZAR per night
  1. Entire condo
  2. Kissimmee
Affordable and so close to Disney
R1,225 ZAR per night
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  1. Entire condo
  2. Kissimmee
Mickey Mouse Themed Getaway next to Disney 2
R1,951 ZAR per night
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  1. Entire condo
  2. Kissimmee
BRAND NEW! Storey Lake Resort DISNEY ORLANDO 206
R2,146 ZAR per night
  1. Entire condo
  2. Orlando
Luxury Waterfront Disney Area Resort! #3
R1,951 ZAR per night
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Spacious 4Bedroom/3.5ba Townhome 15’ from Disney.
R2,530 ZAR per night
SUPERHOST
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  2. Kissimmee
Cozy condo! Lazy river and lake view - 5 ★ Stay
R2,117 ZAR per night

Weekly rentals in Kissimmee

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  1. Private room
  2. Saint Cloud
30 miles from Disney. 40 miles to Melbourne beach
R518 ZAR per night
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  1. Entire home
  2. Kissimmee
Terra Verde 4B Home with Private Pool near Disney
R2,132 ZAR per night
SUPERHOST
  1. Entire home
  2. Kissimmee
3 bedroom Villa in Kissimmee
R1,476 ZAR per night
  1. Entire home
  2. Kissimmee
4 B/3B PRIVATE POOL PORCH PALMS (4461 NP)
R1,576 ZAR per night
  1. Private room
  2. Kissimmee
Private Bathroom & Close Airport,Park & Everything
R726 ZAR per night
SUPERHOST
  1. Private room
  2. Kissimmee
Private bedroom & bath in mansion near Disney
R869 ZAR per night
  1. Entire home
  2. Kissimmee
Prime Disney Location!! 2 BR! Custom Art Work!
R1,843 ZAR per night
SUPERHOST
  1. Private room
  2. Kissimmee
#Room - Comfortable Mickey’s King bed
R632 ZAR per night
SUPERHOST
  1. Private room
  2. Kissimmee
Bedroom, private bath, vacation home near Disney 5
R984 ZAR per night
SUPERHOST
  1. Private room
  2. Kissimmee
Bedroom, private bath, vacation home near Disney 4
R984 ZAR per night
SUPERHOST
  1. Entire home
  2. Kissimmee
Amazing, Cozy 4BD/3BATH, DISNEY AREA, Private Pool
R2,530 ZAR per night
SUPERHOST
  1. Private room
  2. Kissimmee
Nice room with free parking included
R820 ZAR 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.


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.

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