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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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$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
$985,000
▼ $65,000
ENCORE AT REUNION, REUNION WEST
631 Lasso Dr, KISSIMMEE
10
Beds
10
Baths
4,724 SqFt
Single Family Residence
MLS® # S5072544
FEATURED
Active
$780,000
ENCORE AT REUNION
221 Burma St, KISSIMMEE
5
Beds
4
Baths
2,363 SqFt
Single Family Residence
MLS® # S5085514
FEATURED
Active
$599,950
SOLARA RESORT
2190 Fleming Mist Pl, KISSIMMEE
5
Beds
5
Baths
2,283 SqFt
Townhouse
MLS® # S5085203
New
FEATURED
Active
$434,950
PARADISE PALMS RESORT
8954 Candy Palm Rd, KISSIMMEE
4
Beds
3
Baths
1,884 SqFt
Townhouse
MLS® # S5086016
FEATURED
Active
$395,000
COMPASS BAY
5135 Crown Haven Dr, KISSIMMEE
4
Beds
4
Baths
1,637 SqFt
Townhouse
MLS® # S5084225
FEATURED
Active
$379,980
ENCANTADA
3115 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5085909
FEATURED
Active
$379,980
ENCANTADA
3113 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5084425
FEATURED
Active
$333,333
TERRA VERDE VILLAS
4704 Vero Beach Pl, KISSIMMEE
3
Beds
3
Baths
1,286 SqFt
Townhouse
MLS® # S5084253
FEATURED
Active
$275,000
CARIBE COVE
3060 Pirates Retreat Ct 206, KISSIMMEE
3
Beds
2
Baths
1,700 SqFt
Condo - Hotel
MLS® # S5082527
FEATURED
Active
$254,950
CARIBE COVE
3050 Pirates Retreat Ct 101, KISSIMMEE
2
Beds
2
Baths
1,445 SqFt
Condominium
MLS® # S5080538
Active
$5,900,000
HAPPY TRAILS UNIT 04
222 Pawnee Tr, KISSIMMEE
3
Beds
5
Baths
6,559 SqFt
Single Family Residence
MLS® # P4922879
Active
$5,500,000
PLEASANT HILL TRAILS UNIT 01
Twilight Tr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # L4934618
Active
$5,150,000
▼ $540,000
REUNION WEST FAIRWAYS 17 & 18
900 Jack Nicklaus Ct, KISSIMMEE
8
Beds
12
Baths
9,558 SqFt
Single Family Residence
MLS® # O6018108
Active
$5,000,000
ACREAGE & UNREC
3070 Gus Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6073505
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
$3,250,000
ACREAGE & UNREC
1010 Suhls Ln, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6041484
Active
$3,000,000
LOGANS RUN
3555 Boggy Creek Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6073331
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
$2,999,000
▲ $4,000
REUNION WEST FAIRWAYS 17 18
954 Jack Nicklaus Ct, KISSIMMEE
8
Beds
10
Baths
5,896 SqFt
Single Family Residence
MLS® # O6090732
Active
$2,900,000
▼ $300,000
NOT PLATTED
Old Vineland Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # R4906147
Active
$2,895,000
▼ $70,000
REUNION WEST
906 Jack Nicklaus Ct, KISSIMMEE
8
Beds
10
Baths
5,590 SqFt
Single Family Residence
MLS® # O6066876
Active
$2,500,000
ACREAGE & UNREC
4445 Austin Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5979926
Active
$2,450,000
▼ $50,000
ACREAGE & UNREC
West Irlo Bronson Mem Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5072743
Active
$2,400,000
▼ $300,000
ACREAGE & UNREC
East Irlo Bronson Mem Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5055608
Active
$2,200,000
ROLLING OAKS PH 5
8073 Surf St, KISSIMMEE
8
Beds
11
Baths
4,582 SqFt
Single Family Residence
MLS® # O6071066
Active
$2,200,000
KISSIMMEE EXECUTIVE PARK
1020 Dyer Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5074255
Active
$2,200,000
BOBBIE JEAN ACRES
4421 Reaves Rd, KISSIMMEE
5
Beds
6
Baths
5,044 SqFt
Single Family Residence
MLS® # S5031594
Active
$2,175,000
▼ $100,000
ROLLING OAKS PH 6A
8165 Surf St, KISSIMMEE
8
Beds
9
Baths
4,672 SqFt
Single Family Residence
MLS® # S5073570
Active
$2,100,000
CARVER COMMERCIAL CENTER/CRESC
South Poinciana Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5075053
Active
$2,000,000
ACREAGE & UNREC
2125 Cattle Dr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5073546
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
$1,890,000
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
$1,850,000
▼ $150,000
FORMOSA GARDENS UN 2
2812 Sleeping Dragon Ln, KISSIMMEE
8
Beds
8
Baths
6,072 SqFt
Single Family Residence
MLS® # S5075102
Active
$1,800,000
FLA DRAINED LAND CO SUB
1830 Kings Hwy, KISSIMMEE
9
Beds
8
Baths
12,460 SqFt
Single Family Residence
MLS® # S5072279
Active
$1,500,000
▲ $1,498,500
REUNION WEST PH 4
312 Auburn Ave, KISSIMMEE
9
Beds
9
Baths
5,030 SqFt
Single Family Residence
MLS® # O6114137
Active
$1,500,000
HIDDEN HARBOR
2261 Main Sail Cv, KISSIMMEE
4
Beds
5
Baths
6,258 SqFt
Single Family Residence
MLS® # O6101195
Active
$1,500,000
STOREY LAKE PH 3
2909 Fable St, KISSIMMEE
8
Beds
5
Baths
4,303 SqFt
Single Family Residence
MLS® # O6088862
Active
$1,500,000
JOHNSON LILLIE RESUB
50 Lakeview Dr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6017163
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
Active
$1,350,000
EAST LAKE SHORES
1384 East Lakeshore Blvd, KISSIMMEE
4
Beds
4
Baths
3,498 SqFt
Single Family Residence
MLS® # O6108246
New
Active
$1,300,000
REUNION WEST PH 1
7616 Brookhurst Ln, KISSIMMEE
11
Beds
13
Baths
5,496 SqFt
Single Family Residence
MLS® # O6116220
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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