Kissimmee VACATION HOMES FOR SALE

City:  Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion |  Windermere | Winter Garden

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

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FEATURED
Active West Irlo Bronson Memorial Hwy, KISSIMMEE

$13,700,000

▼ $6,300,000 ACREAGE & UNREC

West Irlo Bronson Memorial Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5085096
FEATURED
Active 200 N Hoagland Blvd, KISSIMMEE

$7,700,000

▼ $12,300,000 ACREAGE & UNREC

200 N Hoagland Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5085102
FEATURED
Active 520 Burma St, KISSIMMEE

$1,111,111

ENCORE AT REUNION

520 Burma St, KISSIMMEE

9 Beds 9 Baths 4,630 SqFt Single Family Residence MLS® # S5098246
FEATURED
Active 3008 Parrot Head Pl, KISSIMMEE

$925,000

▼ $74,999 MARGARITAVILLE RESORT ORLANDO

3008 Parrot Head Pl, KISSIMMEE

3 Beds 4 Baths 1,818 SqFt Single Family Residence MLS® # S5091508
FEATURED
Active 7717 Fairfax Dr, KISSIMMEE

$825,000

ENCORE AT REUNION

7717 Fairfax Dr, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Single Family Residence MLS® # S5098281
FEATURED
Active 8983 Amelia Downs Tr, KISSIMMEE

$824,950

▼ $50,000 SOLARA RESORT

8983 Amelia Downs Tr, KISSIMMEE

9 Beds 7 Baths 4,363 SqFt Single Family Residence MLS® # S5086743
FEATURED
Active 220 Pendant Ct, KISSIMMEE

$729,950

ENCORE AT REUNION

220 Pendant Ct, KISSIMMEE

6 Beds 7 Baths 3,317 SqFt Single Family Residence MLS® # S5099537
FEATURED
Active 7613 Wilmington Loop, KISSIMMEE

$729,950

▼ $20,000 ENCORE AT REUNION

7613 Wilmington Loop, KISSIMMEE

6 Beds 6 Baths 2,904 SqFt Single Family Residence MLS® # S5095271
FEATURED
Active 7562 Marker Ave, KISSIMMEE

$729,000

ENCORE AT REUNION

7562 Marker Ave, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Single Family Residence MLS® # S5100653
FEATURED
Active 7552 Marker Ave, KISSIMMEE

$715,000

ENCORE AT REUNION

7552 Marker Ave, KISSIMMEE

6 Beds 7 Baths 3,317 SqFt Single Family Residence MLS® # S5095251
FEATURED
Active 2968 Salted Rim Rd, KISSIMMEE

$685,000

▼ $14,950 MARGARITAVILLE, ROLLING OAKS

2968 Salted Rim Rd, KISSIMMEE

3 Beds 4 Baths 1,818 SqFt Single Family Residence MLS® # S5076132
New FEATURED
Active 8415 Secret Key Cv, KISSIMMEE

$599,950

EMERALD ISLAND RESORT

8415 Secret Key Cv, KISSIMMEE

8 Beds 5 Baths 2,914 SqFt Single Family Residence MLS® # S5101311
FEATURED
Active 8035 Acadia Estates Ct, KISSIMMEE

$589,950

ACADIA ESTATES, WYNDHAM POINTE

8035 Acadia Estates Ct, KISSIMMEE

6 Beds 5 Baths 2,769 SqFt Single Family Residence MLS® # S5098360
FEATURED
Active 4243 Paragraph Dr, KISSIMMEE

$579,950

STOREY LAKE

4243 Paragraph Dr, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Townhouse MLS® # S5096025
FEATURED
Active 141 Madiera Beach Blvd, KISSIMMEE

$539,950

▼ $35,050 TERRA VERDE

141 Madiera Beach Blvd, KISSIMMEE

4 Beds 4 Baths 2,291 SqFt Single Family Residence MLS® # S5094709
FEATURED
Active 2685 Oneida Loop, KISSIMMEE

$535,000

INDIAN CREEK

2685 Oneida Loop, KISSIMMEE

5 Beds 4 Baths 2,136 SqFt Single Family Residence MLS® # S5092783
FEATURED
Active 2190 Fleming Mist Pl, KISSIMMEE

$504,990

▼ $9,960 SOLARA RESORT

2190 Fleming Mist Pl, KISSIMMEE

5 Beds 5 Baths 2,283 SqFt Townhouse MLS® # S5085203
FEATURED
Active 8847 Geneve Ct, KISSIMMEE

$490,000

▼ $9,950 WINDSOR AT WESTSIDE

8847 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5097326
FEATURED
Active 7662 Fitzclarence St, KISSIMMEE

$435,000

WINDSOR HILLS

7662 Fitzclarence St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5098222
FEATURED
Active 2374 Caravelle Cir, KISSIMMEE

$349,950

CORAL CAY RESORT

2374 Caravelle Cir, KISSIMMEE

5 Beds 3 Baths 1,704 SqFt Townhouse MLS® # S5099612
FEATURED
Active 2703 Impala Ln, KISSIMMEE

$299,950

▼ $19,050 REGAL OAKS

2703 Impala Ln, KISSIMMEE

4 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5094178
FEATURED
Active 8504 Crystal Cove Loop, KISSIMMEE

$265,000

▼ $14,950 EMERALD ISLAND

8504 Crystal Cove Loop, KISSIMMEE

3 Beds 3 Baths 1,291 SqFt Townhouse MLS® # S5097343
Active 4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

$7,899,900

▼ $100 ACREAGE & UNREC

4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6158900
Active Twilight Tr, KISSIMMEE

$5,500,000

PLEASANT HILL TRAILS UNIT 01

Twilight Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # L4934618
Active South Goodman Rd, KISSIMMEE

$4,800,000

FLA FRUIT & TRUCKLAND CO

South Goodman Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # R4905868
Active East Irlo Bronson Mem Hwy, KISSIMMEE

$3,315,000

EMERALD LAKE COLONY UN #3

East Irlo Bronson Mem Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6143696
Active 2700 Myers Rd, KISSIMMEE

$3,200,000

▲ $600,000

2700 Myers Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6157530
Active Lots 2 & 3 Sr 535 Rd, KISSIMMEE

$3,200,000

▲ $300,000 TRIANGLE PD

Lots 2 & 3 Sr 535 Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O5918414
Active Polynesian Isle Blvd, KISSIMMEE

$3,000,000

▲ $300,000 CALYPSO CAY COMM PH 02

Polynesian Isle Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O5942296
Active 7952 Jacks Club Dr, KISSIMMEE

$2,999,999

▲ $349,999 REUNION WEST FAIRWAYS 17 & 18

7952 Jacks Club Dr, KISSIMMEE

6 Beds 6 Baths 4,692 SqFt Single Family Residence MLS® # O6181188
Active Old Vineland Rd, KISSIMMEE

$2,500,000

▼ $400,000 NOT PLATTED

Old Vineland Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # R4906147
Active 906 Jack Nicklaus Ct, KISSIMMEE

$2,465,000

▼ $430,000 REUNION WEST

906 Jack Nicklaus Ct, KISSIMMEE

8 Beds 10 Baths 5,590 SqFt Single Family Residence MLS® # O6066876
Active 7443 Gathering Ct, KISSIMMEE

$2,450,000

▲ $255,000 REUNION RESORT

7443 Gathering Ct, KISSIMMEE

9 Beds 10 Baths 5,838 SqFt Single Family Residence MLS® # S5095722
Active West Irlo Bronson Mem Hwy, KISSIMMEE

$2,450,000

▼ $50,000 ACREAGE & UNREC

West Irlo Bronson Mem Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5072743
Active 7925 Jacks Club Ct, KISSIMMEE

$2,399,000

REUNION WEST 17TH & 18TH FAIRW

7925 Jacks Club Ct, KISSIMMEE

5 Beds 6 Baths 4,319 SqFt Single Family Residence MLS® # O6181815
Active 7920 Jacks Club Ct, KISSIMMEE

$2,395,000

REUNION WEST 17TH & 18TH FAIRW

7920 Jacks Club Ct, KISSIMMEE

6 Beds 7 Baths 4,385 SqFt Single Family Residence MLS® # O6170009
Active 8398 Happy Tr, KISSIMMEE

$2,295,000

HAPPY TRAILS SUB

8398 Happy Tr, KISSIMMEE

4 Beds 4 Baths 3,667 SqFt Single Family Residence MLS® # O6156227
Active 955 Jack Nicklaus Ct, KISSIMMEE

$2,249,000

▼ $141,000 REUNION WEST FAIRWAYS 17 & 18

955 Jack Nicklaus Ct, KISSIMMEE

9 Beds 9 Baths 4,590 SqFt Single Family Residence MLS® # O6140238
Active N John Young Pkwy, KISSIMMEE

$2,200,000

ACREAGE & UNREC

N John Young Pkwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5098354
Active Pleasant Hill Rd, KISSIMMEE

$1,950,000

COLLEGE STATION POINCIANA/PLEA

Pleasant Hill Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6154550
Active 7442 Gathering Ct, KISSIMMEE

$1,929,000

▼ $2,000 REUNION PH 01 PRCL 01 UNIT 03

7442 Gathering Ct, KISSIMMEE

10 Beds 10 Baths 5,546 SqFt Single Family Residence MLS® # O6100191
New
Active 222 Pawnee Tr, KISSIMMEE

$1,900,000

HAPPY TRAILS UNIT 4

222 Pawnee Tr, KISSIMMEE

3 Beds 5 Baths 6,559 SqFt Single Family Residence MLS® # O6187856
Active 3060 Parrot Head Pl, KISSIMMEE

$1,895,000

ROLLING OAKS PH 5

3060 Parrot Head Pl, KISSIMMEE

8 Beds 11 Baths 4,518 SqFt Single Family Residence MLS® # O6176550
Active 7928 Jacks Club Ct, KISSIMMEE

$1,850,000

▼ $10,000 REUNION WEST 17TH & 18TH FAIRW

7928 Jacks Club Ct, KISSIMMEE

5 Beds 8 Baths 4,582 SqFt Single Family Residence MLS® # O6134478
Active 8097 Surf St, KISSIMMEE

$1,825,000

▼ $70,000 ROLLING OAKS PH 6A

8097 Surf St, KISSIMMEE

8 Beds 11 Baths 4,092 SqFt Single Family Residence MLS® # O6139323
Active 205 Southfield St, KISSIMMEE

$1,800,000

▲ $150,000 REUNION WEST PH 4

205 Southfield St, KISSIMMEE

13 Beds 13 Baths 6,351 SqFt Single Family Residence MLS® # O6171090
Active 2449 Rama Dr, KISSIMMEE

$1,799,000

▼ $1,000 VERANDA PALMS PH 2B2-2C

2449 Rama Dr, KISSIMMEE

14 Beds 11 Baths 6,255 SqFt Single Family Residence MLS® # O6167020
Active 1501 Sunset Pointe Pl, KISSIMMEE

$1,790,000

SUNSET POINTE

1501 Sunset Pointe Pl, KISSIMMEE

5 Beds 4 Baths 3,685 SqFt Single Family Residence MLS® # S5098141

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.

Communities in Kissimmee, Florida


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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