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Kissimmee VACATION HOMES FOR SALE

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

Kissimmee ResortsBella Vida Resort -  Caribe Cove ResortEmbassy Suites At Sunset Walk - Emerald Island Resort - Encantada - Encore Club at Reunion - Fiesta KeyFormosa ValleyLake Berkley - Lucaya Village - Magic Village - Margaritaville Resort OrlandoParadise PalmsRegal OaksSolara ResortStorey Lake Resort - Summerville Resort - Terra Verde ResortVenetian Bay - Veranda Palms - Villas At Seven Dwarfs LaneWindsor Hills ResortWindsor 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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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 7665 Fairfax Dr, KISSIMMEE

$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 7639 Wilmington Loop, KISSIMMEE

$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 7527 Marker Ave, KISSIMMEE

$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 561 Lasso Dr, KISSIMMEE

$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 350 Pendant Ct, KISSIMMEE

$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 551 Lasso Dr, KISSIMMEE

$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 8953 Zurich Ln, KISSIMMEE

$675,000

WINDSOR AT WESTSIDE

8953 Zurich Ln, KISSIMMEE

7 Beds 6 Baths 3,314 SqFt Single Family Residence MLS® # S5118295
FEATURED
Active 8571 La Isla Dr, KISSIMMEE

$675,000

EMERALD ISLAND RESORT

8571 La Isla Dr, KISSIMMEE

7 Beds 6 Baths 3,599 SqFt Single Family Residence MLS® # S5126510
FEATURED
Active 7751 Tosteth St, KISSIMMEE

$669,999

WINDSOR HILLS

7751 Tosteth St, KISSIMMEE

6 Beds 4 Baths 2,812 SqFt Single Family Residence MLS® # S5128304
FEATURED
Active 7613 Brookhurst Ln, KISSIMMEE

$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 7541 Marker Ave, KISSIMMEE

$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 331 Pendant Ct, KISSIMMEE

$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 1800 Tropical Palms Cir, KISSIMMEE

$629,999

▼ $30,001 SOLARA RESORT

1800 Tropical Palms Cir, KISSIMMEE

5 Beds 5 Baths 2,294 SqFt Townhouse MLS® # S5121304
FEATURED
Active 430 Novi Path, KISSIMMEE

$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 341 Lasso Dr, KISSIMMEE

$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 2561 Montego Bay Blvd, KISSIMMEE

$599,999

MONTEGO BAY

2561 Montego Bay Blvd, KISSIMMEE

4 Beds 4 Baths 2,764 SqFt Single Family Residence MLS® # S5128315
FEATURED
Active 8897 Rhodes St, KISSIMMEE

$598,000

WINDSOR AT WESTSIDE

8897 Rhodes St, KISSIMMEE

6 Beds 5 Baths 3,142 SqFt Single Family Residence MLS® # S5128935
FEATURED
Active 2569 Reading Tr, KISSIMMEE

$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 7719 Comrow St, KISSIMMEE

$549,950

WINDSOR HILLS

7719 Comrow St, KISSIMMEE

4 Beds 4 Baths 1,824 SqFt Single Family Residence MLS® # S5124561
FEATURED
Active 301 Pendant Ct, KISSIMMEE

$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 280 Pendant Ct, KISSIMMEE

$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 8012 Lost Shaker Ln, KISSIMMEE

$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 2685 Oneida Loop, KISSIMMEE

$525,000

INDIAN CREEK

2685 Oneida Loop, KISSIMMEE

5 Beds 4 Baths 2,136 SqFt Single Family Residence MLS® # S5128631
FEATURED
Active 195 Hideaway Beach Ln, KISSIMMEE

$499,999

TERRA VERDE RESORT

195 Hideaway Beach Ln, KISSIMMEE

6 Beds 6 Baths 2,834 SqFt Single Family Residence MLS® # S5129129
FEATURED
Active 8614 La Isla Dr, KISSIMMEE

$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 8886 Geneve Ct, KISSIMMEE

$499,950

WINDSOR AT WESTSIDE

8886 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5119924
FEATURED
Active 3184 Caribbean Soul Dr, KISSIMMEE

$499,000

▼ $96,000 MARGARITAVILLE, ROLLING OAKS

3184 Caribbean Soul Dr, KISSIMMEE

4 Beds 3 Baths 1,712 SqFt Townhouse MLS® # S5103875
FEATURED
Active 4981 Windermere Ave, KISSIMMEE

$489,980

STOREY LAKE RESORT

4981 Windermere Ave, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Townhouse MLS® # S5128849
FEATURED
Active 2993 Sunset Vista Blvd, KISSIMMEE

$489,000

SUNSET LAKES

2993 Sunset Vista Blvd, KISSIMMEE

4 Beds 3 Baths 1,700 SqFt Single Family Residence MLS® # S5123939
FEATURED
Active 2427 Dubai St, KISSIMMEE

$479,950

▼ $10,000 WINDSOR AT WESTSIDE

2427 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Townhouse MLS® # S5123971
FEATURED
Active 4739 Cumbrian Lakes Dr, KISSIMMEE

$474,950

CUMBRIAN LAKES RESORT

4739 Cumbrian Lakes Dr, KISSIMMEE

5 Beds 5 Baths 2,561 SqFt Single Family Residence MLS® # S5125941
FEATURED
Active 2610 Sunrise Shores Dr, KISSIMMEE

$469,950

SUMMERVILLE RESORT

2610 Sunrise Shores Dr, KISSIMMEE

4 Beds 6 Baths 1,804 SqFt Townhouse MLS® # S5123862
FEATURED
Active 932 Emerald Green Ct, KISSIMMEE

$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 8912 Sydney Ave, KISSIMMEE

$449,000

▲ $4,556 WINDSOR AT WESTSIDE

8912 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5115540
FEATURED
Active 3015 Yellow Lantana Ln, KISSIMMEE

$430,000

ENCANTADA

3015 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Townhouse MLS® # S5126724
FEATURED
Active 3013 Sea Plane Ln, KISSIMMEE

$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 3037 Sea Plane Ln, KISSIMMEE

$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 3075 Key Lime Loop, KISSIMMEE

$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 2585 Maneshaw Ln, KISSIMMEE

$405,000

WINDSOR HILLS RESORT

2585 Maneshaw Ln, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5129516
FEATURED
Active 1560 The Oaks Blvd, KISSIMMEE

$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 3083 Yellow Lantana Ln, KISSIMMEE

$370,000

▼ $10,000 ENCANTADA

3083 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,340 SqFt Townhouse MLS® # S5116892
FEATURED
Active 2322 Silver Palm Dr, KISSIMMEE

$349,999

WINDSOR PALMS

2322 Silver Palm Dr, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5126708
FEATURED
Active 2374 Caravelle Cir, KISSIMMEE

$320,000

▼ $29,950 CORAL CAY RESORT

2374 Caravelle Cir, KISSIMMEE

5 Beds 3 Baths 1,704 SqFt Townhouse MLS® # S5099612
FEATURED
Active 2606 Roadster Ln, KISSIMMEE

$315,000

REGAL OAKS

2606 Roadster Ln, KISSIMMEE

2 Beds 3 Baths 1,350 SqFt Townhouse MLS® # S5120739
FEATURED
Active 2200 San Zanobi Dr 108, KISSIMMEE

$310,000

VENETIAN BAY

2200 San Zanobi Dr 108, KISSIMMEE

4 Beds 3 Baths 1,470 SqFt Condominium MLS® # S5102991
FEATURED
Active 7526 Pellham Way, KISSIMMEE

$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 contact a Team Donovan agent online today or call 407-705-2616.

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