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

 

Sold
918 JACK NICKLAUS CT,

918 Jack Nicklaus Ct, Kissimmee

6882992
A palatial 2-storey home located in Bears Den, a Jack Nicklaus golf course community, with a sprawling green vista. This one of a kind custo …more
$3,100,000
4445 AUSTIN RD,

4445 Austin Rd, Kissimmee

3226242
Possibilities are endless. This is a remarkable opportunity for an investor/builder looking to develop a small new subdivision of single-fam …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 floorplan here in Margaritaville Resort Orlando! This 4689 …more
$2,499,500
Sold
1015 JACK NICKLAUS CT,

1015 Jack Nicklaus Ct, Kissimmee

8959202
Investor’s Dream! This Magnificent Rental Home located in the heart of the Exclusive Bear’s Den gated community is a 3 story Masterpiece lo …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! Beautiful country setting with private access to East Lake …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 opportunity. Imagine yourself driving in through the private ga …more
$2,200,000
1503 SUNSET POINTE PL,

1503 Sunset Pointe Pl, Kissimmee

5440632
This Elegant Florida style Home with breathtaking sunsets illuminating the sky this 5 bed, 4 bath plus bonus room and office with over 4,000 …more
$2,150,000
Sold
701 HARGROVE LN,

701 Hargrove Ln, Kissimmee

6667242
High End Custom Luxury Tuscan style mansion located on 5 acre private Property near Disney World. Nestled between Champions Gate, Reunion Re …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. This Signature Jack Nicklaus Community Offers Unparalleled …more
$2,100,000
3056 PARROT HEAD PL,

3056 Parrot Head Pl, Kissimmee

8941312
SPECTACULAR WATERFRONT Cottage on Margaritaville Resort Orlando’s ‘Trophy Row’! FANTASTIC OPPORTUNITY TO OWN ONE of the LARGEST WATERFRONT C …more
$1,950,000
Sold
948 JACK NICKLAUS CT,

948 Jack Nicklaus Ct, Kissimmee

4751612
This MAJESTIC, Modern Home is Situated on the 18th Green of the Jack Nicklaus Signature Golf Course Featuring West Facing Scenic Sunset View …more
$1,750,000
8145 SURF ST,

8145 Surf St, Kissimmee

6635632
Incredible 6 Bedroom WATER FRONT cottage with private pool and spa located in the heart of Margaritaville Resort just 5 minutes from Disney! …more
$1,700,000

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.