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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!
Search Kissimmee Real Estate Listings
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Under $100,000
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$100,000 - $200,000
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$500,000 - $600,000
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$800,000 - $900,000
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$900,000 - $1,000,000
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Over $1,000,000
FEATURED
Active
$20,000,000
ACREAGE & UNREC
West Irlo Bronson Memorial Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5085096
FEATURED
Active
$20,000,000
ACREAGE & UNREC
200 N Hoagland Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5085102
FEATURED
Active
$999,999
MARGARITAVILLE RESORT ORLANDO
3008 Parrot Head Pl, KISSIMMEE
3
Beds
4
Baths
1,818 SqFt
Single Family Residence
MLS® # S5091508
FEATURED
Active
$995,000
ENCORE AT REUNION
7648 Wilmington Loop, KISSIMMEE
9
Beds
9
Baths
4,630 SqFt
Single Family Residence
MLS® # S5091283
FEATURED
Active
$975,000
▼ $20,000
SOLARA RESORT
8983 Amelia Downs Tr, KISSIMMEE
9
Beds
7
Baths
4,363 SqFt
Single Family Residence
MLS® # S5086743
New
FEATURED
Active
$599,950
EMERALD ISLAND RESORT
8579 La Isla Dr, KISSIMMEE
7
Beds
5
Baths
2,881 SqFt
Single Family Residence
MLS® # S5091701
FEATURED
Active
$575,000
▼ $24,950
SOLARA RESORT
2190 Fleming Mist Pl, KISSIMMEE
5
Beds
5
Baths
2,283 SqFt
Townhouse
MLS® # S5085203
FEATURED
Active
$449,950
▼ $35,050
CRYSTAL COVE RESORT
945 Emerald Green Ct, KISSIMMEE
4
Beds
3
Baths
2,078 SqFt
Single Family Residence
MLS® # S5088384
FEATURED
Active
$356,500
▼ $23,480
ENCANTADA
3115 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5085909
FEATURED
Active
$356,500
▼ $23,480
ENCANTADA
3113 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5084425
FEATURED
Active
$346,000
WINDSOR HILLS RESORT
2821 Almaton Loop 403, KISSIMMEE
3
Beds
2
Baths
1,246 SqFt
Condominium
MLS® # S5090589
FEATURED
Active
$319,950
▼ $28,000
ENCANTADA
8589 Bay Lilly Loop, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5088854
FEATURED
Active
$310,000
▼ $23,333
TERRA VERDE VILLAS
4704 Vero Beach Pl, KISSIMMEE
3
Beds
3
Baths
1,286 SqFt
Townhouse
MLS® # S5084253
FEATURED
Active
$225,000
CARIBE COVE
9051 Treasure Trove Ln 108, KISSIMMEE
2
Beds
2
Baths
1,445 SqFt
Condo - Hotel
MLS® # S5089968
Active
$5,500,000
PLEASANT HILL TRAILS UNIT 01
Twilight Tr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # L4934618
Active
$5,000,000
ACREAGE & UNREC
3070 Gus Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6073505
Active
$5,000,000
▲ $2,000,000
LOGANS RUN
3555 Boggy Creek Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6073331
Active
$4,800,000
FLA FRUIT & TRUCKLAND CO
South Goodman Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # R4905868
Active
$4,200,000
ORANGE BLOSSOM ADD
4011 South Orange Blossom Tr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6054839
Active
$3,500,000
ACREAGE & UNREC
3060 Gus Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6125360
New
Active
$3,315,000
EMERALD LAKE COLONY UN #3
East Irlo Bronson Mem Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6143696
Active
$3,200,000
▲ $300,000
TRIANGLE PD
Lots 2 & 3 Sr 535 Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5918414
Active
$3,150,000
▼ $100,000
ACREAGE & UNREC
1010 Suhls Ln, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6041484
Active
$3,000,000
▲ $300,000
CALYPSO CAY COMM PH 02
Polynesian Isle Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5942296
Active
$2,900,000
▼ $300,000
NOT PLATTED
Old Vineland Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # R4906147
Active
$2,500,000
ACREAGE & UNREC
4445 Austin Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5979926
Active
$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
$2,399,000
REUNION WEST FAIRWAYS 17 & 18
955 Jack Nicklaus Ct, KISSIMMEE
9
Beds
9
Baths
4,590 SqFt
Single Family Residence
MLS® # O6140238
Active
$2,300,000
REGAL POINT WEST
1300 Grandview Blvd, KISSIMMEE
5
Beds
6
Baths
6,176 SqFt
Single Family Residence
MLS® # G5072774
New
Active
$1,950,000
ROLLING OAKS PH 6A
8097 Surf St, KISSIMMEE
8
Beds
11
Baths
4,092 SqFt
Single Family Residence
MLS® # O6139323
Active
$1,935,900
REUNION PH 01 PRCL 01 UNIT 03
7442 Gathering Ct, KISSIMMEE
10
Beds
10
Baths
5,546 SqFt
Single Family Residence
MLS® # O6100191
Active
$1,900,000
2221 West Martin St, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6118616
Active
$1,890,000
SUNSET POINTE
1501 Sunset Pointe Pl, KISSIMMEE
5
Beds
4
Baths
3,685 SqFt
Single Family Residence
MLS® # S5085644
Active
$1,883,000
ACREAGE & UNREC
North Hoagland Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6085435
Active
$1,870,000
▼ $20,000
REUNION WEST 17TH & 18TH FAIRW
7928 Jacks Club Ct, KISSIMMEE
5
Beds
8
Baths
4,582 SqFt
Single Family Residence
MLS® # O6134478
Active
$1,850,000
▼ $150,000
FORMOSA GARDENS UN 2
2812 Sleeping Dragon Ln, KISSIMMEE
8
Beds
8
Baths
6,072 SqFt
Single Family Residence
MLS® # S5075102
Active
$1,760,000
▼ $20,000
REUNION WEST 17TH & 18TH FAIRW
7924 Jacks Club Ct, KISSIMMEE
4
Beds
5
Baths
4,195 SqFt
Single Family Residence
MLS® # O6134483
Active
$1,700,000
▼ $1,000,000
REUNION RESORT
1427 Fairview Cir, KISSIMMEE
5
Beds
5
Baths
3,556 SqFt
Single Family Residence
MLS® # S5091319
Active
$1,689,930
▼ $10
VERANDA PALMS PH 2B2-2C
2409 Shanti Dr, KISSIMMEE
15
Beds
17
Baths
6,249 SqFt
Single Family Residence
MLS® # S5086571
Active
$1,680,000
VERANDA PALMS PH 2B2-2C
2359 Rama Dr, KISSIMMEE
15
Beds
17
Baths
6,374 SqFt
Single Family Residence
MLS® # O6121444
Active
$1,500,000
REUNION WEST PH 4
312 Auburn Ave, KISSIMMEE
9
Beds
9
Baths
5,030 SqFt
Single Family Residence
MLS® # O6131665
Active
$1,500,000
TOHOP ESTATES
Granada Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S4856294
Active
$1,499,990
ACREAGE & UNREC
1560 Turkey Ln, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6070355
New
Active
$1,400,000
JOHNSON LILLIE RESUB
50 Lakeview Dr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5091781
Active
$1,395,000
▼ $95,000
HAPPY TRAILS SUB
8550 Sweetwater Tr, KISSIMMEE
5
Beds
4
Baths
4,253 SqFt
Single Family Residence
MLS® # O6120036
Active
$1,350,000
REUNION WEST PH 2A WEST
241 Falls Dr, KISSIMMEE
11
Beds
13
Baths
5,496 SqFt
Single Family Residence
MLS® # S5091333
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.
Browse Kissimmee Holiday Home Communities:
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 or call 407-705-2616.
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