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!


Search Kissimmee Real Estate Listings

 

918 JACK NICKLAUS CT,

918 Jack Nicklaus Ct, Kissimmee

6882992
A palatial 2-storey home located in Bears Den, a Jack Nicklaus golf course commu …more
$3,800,000
4445 AUSTIN RD,

4445 Austin Rd, Kissimmee

3226242
Possibilities are endless. This is a remarkable opportunity for an investor/buil …more
$2,500,000
3102 PARROT HEAD PL,

3102 Parrot Head Pl, Kissimmee

8948152
Uniquely rare opportunity to own the largest 8 bedroom, 9 bathroom vacation home …more
$2,499,500
1015 JACK NICKLAUS CT,

1015 Jack Nicklaus Ct, Kissimmee

8959202
Investor’s Dream! This Magnificent Rental Home located in the heart of the Exclu …more
$2,450,000
2960 FRONTIER DR,

2960 Frontier Dr, Kissimmee

5554642
Unique 10.1 acre estate in the perfect location for privacy, convenience and fun …more
$2,400,000
4421 REAVES RD,

4421 Reaves Rd, Kissimmee

5650442
This stunning, custom designed and custom built home is a once in a lifetime opp …more
$2,200,000
701 HARGROVE LN,

701 Hargrove Ln, Kissimmee

6667242
High End Custom Luxury Tuscan style mansion located on 5 acre private Property n …more
$2,144,077
1063 JACK NICKLAUS CT,

1063 Jack Nicklaus Ct, Kissimmee

71059442
Welcome to the Exclusive Bear’s Den Neighborhood Located Within Reunion Resort. …more
$2,100,000
948 JACK NICKLAUS CT,

948 Jack Nicklaus Ct, Kissimmee

4751612
This MAJESTIC, Modern Home is Situated on the 18th Green of the Jack Nicklaus Si …more
$1,750,000
899 SPRING PARK LOOP,

899 Spring Park Loop, Kissimmee

4649382
SOLD DATA ENTRY!!!CUSTOM ESTATE HOME!!! …more
$1,525,000
7932 JACKS CLUB CT,

7932 Jacks Club Ct, Kissimmee

6743452
One or more photo(s) has been virtually staged. Under Construction. Estimated co …more
$1,476,250
3060 PARROT HEAD PL,

3060 Parrot Head Pl, Kissimmee

81145182
LOCATION LOCATION LOCATION! Located on TROPHY ROW! Rare Opportunity! This gorgeo …more
$1,455,000

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.