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Kissimmee, FL Vacation Homes

What do the popular theme parks Walt Disney World, Universal Orlando and Sea World have in common? They’re located right next door to Kissimmee, Florida. The city is located just outside Orlando in Osceola County, and is one of the fastest growing communities in Florida.

Kissimmee is a family-friendly community that is not only a great place to visit, but a better place to call home. Many people who visit from cold weather states like Michigan and New York, as well as frequent travelers from Canada and Europe, find Kissimmee so appealing that they buy second homes here. It’s no wonder because Kissimmee vacation homes offer great access to a thriving downtown district and a high level of municipal services.

Check out the available Kissimmee vacation real estate below, or continue reading to learn more about the many wonderful holiday communities found in the city!

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FEATURED
Active 631 Lasso Dr, KISSIMMEE

$985,000

▼ $65,000 ENCORE AT REUNION, REUNION WEST

631 Lasso Dr, KISSIMMEE

10 Beds 10 Baths 4,724 SqFt Single Family Residence MLS® # S5072544
FEATURED
Active 601 Lasso Dr, KISSIMMEE

$779,950

ENCORE AT REUNION, REUNION WEST

601 Lasso Dr, KISSIMMEE

6 Beds 7 Baths 3,099 SqFt Single Family Residence MLS® # S5079651
FEATURED
Active 2513 Calla Lily Cv, KISSIMMEE

$534,950

CRESCENT LAKES, CALLA LILY COVE

2513 Calla Lily Cv, KISSIMMEE

7 Beds 3 Baths 2,679 SqFt Single Family Residence MLS® # S5076964
FEATURED
Active 931 Marcello Blvd, KISSIMMEE

$459,950

BELLAVIDA

931 Marcello Blvd, KISSIMMEE

4 Beds 3 Baths 1,647 SqFt Single Family Residence MLS® # S5079598
FEATURED
Active 155 Barefoot Beach Way, KISSIMMEE

$449,950

▼ $10,000 TERRA VERDE

155 Barefoot Beach Way, KISSIMMEE

4 Beds 2 Baths 1,940 SqFt Single Family Residence MLS® # S5075650
FEATURED
Active 7802 Indian Ridge Tr S, KISSIMMEE

$449,950

INDIAN RIDGE

7802 Indian Ridge Tr S, KISSIMMEE

4 Beds 2 Baths 1,971 SqFt Single Family Residence MLS® # S5079024
FEATURED
Active 2934 Dickens Cir, KISSIMMEE

$439,950

LINDFIELDS

2934 Dickens Cir, KISSIMMEE

4 Beds 3 Baths 2,210 SqFt Single Family Residence MLS® # S5077284
New FEATURED
Active 2558 Renshaw St, KISSIMMEE

$435,000

WINDSOR HILLS, VISTAS

2558 Renshaw St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5079795
FEATURED
Active 2418 Willow Tree Ln, KISSIMMEE

$349,950

CRESCENT LAKES, WILLOW BEND

2418 Willow Tree Ln, KISSIMMEE

3 Beds 2 Baths 1,386 SqFt Single Family Residence MLS® # S5078493
New FEATURED
Active 4005 Santa Maria Dr 104, KISSIMMEE

$272,000

VENETIAN BAY VILLAGE

4005 Santa Maria Dr 104, KISSIMMEE

3 Beds 2 Baths 1,296 SqFt Condominium MLS® # S5079922
FEATURED
Active 3156 Tamarind Cir, KISSIMMEE

$269,950

VILLAGES AT MANGO KEY

3156 Tamarind Cir, KISSIMMEE

2 Beds 2 Baths 1,012 SqFt Townhouse MLS® # S5075852
Active 222 Pawnee Tr, KISSIMMEE

$5,900,000

HAPPY TRAILS UNIT 04

222 Pawnee Tr, KISSIMMEE

3 Beds 5 Baths 6,559 SqFt Single Family Residence MLS® # P4922879

The Kissimmee Community

The city’s unusual name is said to be the modern spelling of a tribal word from one of Florida’s lesser-known tribes, the Jororo. A 1752 Spanish map used the name “Cacema,” which has evolved into today’s spelling of Kissimmee.

In the early to mid-20th century, Kissimmee’s economy was based on cattle, citrus and other crops. Retirees were encouraged to move here in the 1950’s. Kissimmee real estate really took off after Walt Disney World was built in the 1970’s. Since then, other theme parks and attractions followed, such as Fun Spot America, Gatorland, Kissimmee Air Museum, as well as several dinner theaters and miniature golf parks.

Kissimmee Real Estate Market

Kissimmee vacation home buyers also choose the city because of the wide range of parks and recreational activities that are available, including Lake Tohopekaliga, which offers some of the best bass fishing in the world.

Nature lovers can enjoy a thrilling airboat ride and discover a world alive with tropical birds, turtles and alligators. There are plenty of championship golf courses nearby that are ideal for the beginner or professional golfer. And you’ll find a mix of dining options and unique shopping venues in the area too.

One reason people buy Kissimmee vacation real estate as a second home is to generate income by renting out the property to visitors. If you’d like more information about the homes for sale in Kissimmee that can be rented as a vacation property, please contact a Team Donovan agent online today or call 407-705-2616.

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