Kissimmee VACATION HOMES FOR SALE
City: Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion | Windermere | Winter Garden
Kissimmee Resorts: Bella Vida Resort - Caribe Cove Resort - Embassy Suites At Sunset Walk - Emerald Island Resort - Encantada - Encore Club at Reunion - Fiesta Key - Formosa Valley - Lake Berkley - Lucaya Village - Magic Village - Margaritaville Resort Orlando - Paradise Palms - Regal Oaks - Solara Resort - Storey Lake Resort - Summerville Resort - Terra Verde Resort - Venetian Bay - Veranda Palms - Villas At Seven Dwarfs Lane - Windsor Hills Resort - Windsor Palms Resort
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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$400,000 - $500,000
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$500,000 - $600,000
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$900,000 - $1,000,000
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Over $1,000,000
FEATURED
Active
$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
$7,700,000
▼ $12,300,000
ACREAGE & UNREC
200 N Hoagland Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5085102
FEATURED
Active
$1,350,000
ENCORE AT REUNION, REUNION WEST
7665 Fairfax Dr, KISSIMMEE
11
Beds
13
Baths
5,496 SqFt
Single Family Residence
MLS® # S5123395
FEATURED
Active
$988,999
▼ $11,000
ENCORE AT REUNION, REUNION RESORT
7639 Wilmington Loop, KISSIMMEE
11
Beds
10
Baths
4,707 SqFt
Single Family Residence
MLS® # S5116680
FEATURED
Active
$825,000
ENCORE AT REUNION, REUNION WEST
7527 Marker Ave, KISSIMMEE
8
Beds
6
Baths
3,612 SqFt
Single Family Residence
MLS® # S5126948
FEATURED
Active
$719,950
ENCORE AT REUNION, REUNION WEST
561 Lasso Dr, KISSIMMEE
8
Beds
7
Baths
3,401 SqFt
Single Family Residence
MLS® # S5120195
FEATURED
Active
$719,950
ENCORE AT REUNION, REUNION WEST
350 Pendant Ct, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5120062
FEATURED
Active
$699,999
ENCORE AT REUNION, REUNION WEST
551 Lasso Dr, KISSIMMEE
8
Beds
7
Baths
3,401 SqFt
Single Family Residence
MLS® # S5128532
FEATURED
Active
$675,000
WINDSOR AT WESTSIDE
8953 Zurich Ln, KISSIMMEE
7
Beds
6
Baths
3,314 SqFt
Single Family Residence
MLS® # S5118295
FEATURED
Active
$675,000
EMERALD ISLAND RESORT
8571 La Isla Dr, KISSIMMEE
7
Beds
6
Baths
3,599 SqFt
Single Family Residence
MLS® # S5126510
FEATURED
Active
$669,999
WINDSOR HILLS
7751 Tosteth St, KISSIMMEE
6
Beds
4
Baths
2,812 SqFt
Single Family Residence
MLS® # S5128304
FEATURED
Active
$669,789
ENCORE AT REUNION, REUNION WEST
7613 Brookhurst Ln, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5128335
FEATURED
Active
$669,456
ENCORE AT REUNION, REUNION WEST
7541 Marker Ave, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5128347
FEATURED
Active
$669,123
ENCORE AT REUNION, REUNION WEST
331 Pendant Ct, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5128341
FEATURED
Active
$629,999
▼ $30,001
SOLARA RESORT
1800 Tropical Palms Cir, KISSIMMEE
5
Beds
5
Baths
2,294 SqFt
Townhouse
MLS® # S5121304
FEATURED
Active
$624,999
▼ $24,951
ENCORE AT REUNION, REUNION WEST
430 Novi Path, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5120422
FEATURED
Active
$599,999
ENCORE AT REUNION, REUNION WEST
341 Lasso Dr, KISSIMMEE
6
Beds
6
Baths
2,936 SqFt
Single Family Residence
MLS® # S5127732
FEATURED
Active
$599,999
MONTEGO BAY
2561 Montego Bay Blvd, KISSIMMEE
4
Beds
4
Baths
2,764 SqFt
Single Family Residence
MLS® # S5128315
FEATURED
Active
$598,000
WINDSOR AT WESTSIDE
8897 Rhodes St, KISSIMMEE
6
Beds
5
Baths
3,142 SqFt
Single Family Residence
MLS® # S5128935
FEATURED
Active
$575,000
▼ $24,999
STOREY LAKE, COVE AT STOREY LAKE
2569 Reading Tr, KISSIMMEE
4
Beds
3
Baths
2,168 SqFt
Townhouse
MLS® # S5122098
FEATURED
Active
$549,950
WINDSOR HILLS
7719 Comrow St, KISSIMMEE
4
Beds
4
Baths
1,824 SqFt
Single Family Residence
MLS® # S5124561
FEATURED
Active
$540,000
▼ $10,000
ENCORE AT REUNION, REUNION WEST
301 Pendant Ct, KISSIMMEE
5
Beds
5
Baths
2,570 SqFt
Single Family Residence
MLS® # S5121431
FEATURED
Active
$539,950
▼ $10,000
ENCORE AT REUNION, REUNION RESORT
280 Pendant Ct, KISSIMMEE
5
Beds
5
Baths
2,570 SqFt
Single Family Residence
MLS® # S5112064
FEATURED
Active
$529,950
▼ $20,000
MARGARITAVILLE, ROLLING OAKS
8012 Lost Shaker Ln, KISSIMMEE
4
Beds
4
Baths
1,850 SqFt
Single Family Residence
MLS® # S5121104
FEATURED
Active
$525,000
INDIAN CREEK
2685 Oneida Loop, KISSIMMEE
5
Beds
4
Baths
2,136 SqFt
Single Family Residence
MLS® # S5128631
FEATURED
Active
$499,999
TERRA VERDE RESORT
195 Hideaway Beach Ln, KISSIMMEE
6
Beds
6
Baths
2,834 SqFt
Single Family Residence
MLS® # S5129129
FEATURED
Active
$499,999
▼ $15,516
EMERALD ISLAND RESORT
8614 La Isla Dr, KISSIMMEE
5
Beds
4
Baths
2,317 SqFt
Single Family Residence
MLS® # S5119558
FEATURED
Active
$499,950
WINDSOR AT WESTSIDE
8886 Geneve Ct, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5119924
FEATURED
Active
$499,000
▼ $96,000
MARGARITAVILLE, ROLLING OAKS
3184 Caribbean Soul Dr, KISSIMMEE
4
Beds
3
Baths
1,712 SqFt
Townhouse
MLS® # S5103875
FEATURED
Active
$489,980
STOREY LAKE RESORT
4981 Windermere Ave, KISSIMMEE
4
Beds
3
Baths
1,914 SqFt
Townhouse
MLS® # S5128849
FEATURED
Active
$489,000
SUNSET LAKES
2993 Sunset Vista Blvd, KISSIMMEE
4
Beds
3
Baths
1,700 SqFt
Single Family Residence
MLS® # S5123939
FEATURED
Active
$479,950
▼ $10,000
WINDSOR AT WESTSIDE
2427 Dubai St, KISSIMMEE
5
Beds
5
Baths
2,265 SqFt
Townhouse
MLS® # S5123971
FEATURED
Active
$474,950
CUMBRIAN LAKES RESORT
4739 Cumbrian Lakes Dr, KISSIMMEE
5
Beds
5
Baths
2,561 SqFt
Single Family Residence
MLS® # S5125941
FEATURED
Active
$469,950
SUMMERVILLE RESORT
2610 Sunrise Shores Dr, KISSIMMEE
4
Beds
6
Baths
1,804 SqFt
Townhouse
MLS® # S5123862
FEATURED
Active
$449,950
▼ $9,550
CRYSTAL COVE RESORT
932 Emerald Green Ct, KISSIMMEE
4
Beds
3
Baths
1,808 SqFt
Single Family Residence
MLS® # S5124539
FEATURED
Active
$449,000
▲ $4,556
WINDSOR AT WESTSIDE
8912 Sydney Ave, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5115540
FEATURED
Active
$430,000
ENCANTADA
3015 Yellow Lantana Ln, KISSIMMEE
4
Beds
3
Baths
1,636 SqFt
Townhouse
MLS® # S5126724
FEATURED
Active
$424,999
▼ $24,951
MARGARITAVILLE, ROLLING OAKS
3013 Sea Plane Ln, KISSIMMEE
4
Beds
3
Baths
1,410 SqFt
Single Family Residence
MLS® # S5123757
FEATURED
Active
$424,500
▼ $15,450
MARGARITAVILLE, ROLLING OAKS
3037 Sea Plane Ln, KISSIMMEE
2
Beds
3
Baths
1,305 SqFt
Single Family Residence
MLS® # S5112270
FEATURED
Active
$409,000
▼ $20,000
MARGARITAVILLE, ROLLING OAKS
3075 Key Lime Loop, KISSIMMEE
2
Beds
3
Baths
1,305 SqFt
Single Family Residence
MLS® # S5115878
New
FEATURED
Active
$405,000
WINDSOR HILLS RESORT
2585 Maneshaw Ln, KISSIMMEE
3
Beds
3
Baths
1,440 SqFt
Townhouse
MLS® # S5129516
FEATURED
Active
$399,950
THE OAKS, OAKS, OVEROAKS
1560 The Oaks Blvd, KISSIMMEE
3
Beds
2
Baths
1,538 SqFt
Single Family Residence
MLS® # S5126508
FEATURED
Active
$370,000
▼ $10,000
ENCANTADA
3083 Yellow Lantana Ln, KISSIMMEE
4
Beds
3
Baths
1,340 SqFt
Townhouse
MLS® # S5116892
FEATURED
Active
$349,999
WINDSOR PALMS
2322 Silver Palm Dr, KISSIMMEE
3
Beds
3
Baths
1,440 SqFt
Townhouse
MLS® # S5126708
FEATURED
Active
$320,000
▼ $29,950
CORAL CAY RESORT
2374 Caravelle Cir, KISSIMMEE
5
Beds
3
Baths
1,704 SqFt
Townhouse
MLS® # S5099612
FEATURED
Active
$315,000
REGAL OAKS
2606 Roadster Ln, KISSIMMEE
2
Beds
3
Baths
1,350 SqFt
Townhouse
MLS® # S5120739
FEATURED
Active
$310,000
VENETIAN BAY
2200 San Zanobi Dr 108, KISSIMMEE
4
Beds
3
Baths
1,470 SqFt
Condominium
MLS® # S5102991
FEATURED
Active
$299,999
OAKWATER
7526 Pellham Way, KISSIMMEE
3
Beds
2
Baths
1,427 SqFt
Condominium
MLS® # S5122847
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 or call 407-705-2616.
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