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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!

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FEATURED
Active West Irlo Bronson Memorial Hwy, KISSIMMEE

$20,000,000

ACREAGE & UNREC

West Irlo Bronson Memorial Hwy, KISSIMMEE

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

$20,000,000

ACREAGE & UNREC

200 N Hoagland Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5085102
FEATURED
Active 631 Lasso Dr, KISSIMMEE

$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 221 Burma St, KISSIMMEE

$780,000

ENCORE AT REUNION

221 Burma St, KISSIMMEE

5 Beds 4 Baths 2,363 SqFt Single Family Residence MLS® # S5085514
FEATURED
Active 2190 Fleming Mist Pl, KISSIMMEE

$599,950

SOLARA RESORT

2190 Fleming Mist Pl, KISSIMMEE

5 Beds 5 Baths 2,283 SqFt Townhouse MLS® # S5085203
New FEATURED
Active 8954 Candy Palm Rd, KISSIMMEE

$434,950

PARADISE PALMS RESORT

8954 Candy Palm Rd, KISSIMMEE

4 Beds 3 Baths 1,884 SqFt Townhouse MLS® # S5086016
FEATURED
Active 5135 Crown Haven Dr, KISSIMMEE

$395,000

COMPASS BAY

5135 Crown Haven Dr, KISSIMMEE

4 Beds 4 Baths 1,637 SqFt Townhouse MLS® # S5084225
FEATURED
Active 3115 Yellow Lantana Ln, KISSIMMEE

$379,980

ENCANTADA

3115 Yellow Lantana Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5085909
FEATURED
Active 3113 Yellow Lantana Ln, KISSIMMEE

$379,980

ENCANTADA

3113 Yellow Lantana Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5084425
FEATURED
Active 4704 Vero Beach Pl, KISSIMMEE

$333,333

TERRA VERDE VILLAS

4704 Vero Beach Pl, KISSIMMEE

3 Beds 3 Baths 1,286 SqFt Townhouse MLS® # S5084253
FEATURED
Active 3060 Pirates Retreat Ct 206, KISSIMMEE

$275,000

CARIBE COVE

3060 Pirates Retreat Ct 206, KISSIMMEE

3 Beds 2 Baths 1,700 SqFt Condo - Hotel MLS® # S5082527
FEATURED
Active 3050 Pirates Retreat Ct 101, KISSIMMEE

$254,950

CARIBE COVE

3050 Pirates Retreat Ct 101, KISSIMMEE

2 Beds 2 Baths 1,445 SqFt Condominium MLS® # S5080538
Active 222 Pawnee Tr, KISSIMMEE

$5,900,000

HAPPY TRAILS UNIT 04

222 Pawnee Tr, KISSIMMEE

3 Beds 5 Baths 6,559 SqFt Single Family Residence MLS® # P4922879
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 900 Jack Nicklaus Ct, KISSIMMEE

$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 3070 Gus Rd, KISSIMMEE

$5,000,000

ACREAGE & UNREC

3070 Gus Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6073505
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 4011 South Orange Blossom Tr, KISSIMMEE

$4,200,000

ORANGE BLOSSOM ADD

4011 South Orange Blossom Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6054839
Active 1010 Suhls Ln, KISSIMMEE

$3,250,000

ACREAGE & UNREC

1010 Suhls Ln, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6041484
Active 3555 Boggy Creek Rd, KISSIMMEE

$3,000,000

LOGANS RUN

3555 Boggy Creek Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6073331
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 954 Jack Nicklaus Ct, KISSIMMEE

$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 Old Vineland Rd, KISSIMMEE

$2,900,000

▼ $300,000 NOT PLATTED

Old Vineland Rd, KISSIMMEE

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

$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 4445 Austin Rd, KISSIMMEE

$2,500,000

ACREAGE & UNREC

4445 Austin Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O5979926
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 East Irlo Bronson Mem Hwy, KISSIMMEE

$2,400,000

▼ $300,000 ACREAGE & UNREC

East Irlo Bronson Mem Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5055608
Active 8073 Surf St, KISSIMMEE

$2,200,000

ROLLING OAKS PH 5

8073 Surf St, KISSIMMEE

8 Beds 11 Baths 4,582 SqFt Single Family Residence MLS® # O6071066
Active 1020 Dyer Blvd, KISSIMMEE

$2,200,000

KISSIMMEE EXECUTIVE PARK

1020 Dyer Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5074255
Active 4421 Reaves Rd, KISSIMMEE

$2,200,000

BOBBIE JEAN ACRES

4421 Reaves Rd, KISSIMMEE

5 Beds 6 Baths 5,044 SqFt Single Family Residence MLS® # S5031594
Active 8165 Surf St, KISSIMMEE

$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 South Poinciana Blvd, KISSIMMEE

$2,100,000

CARVER COMMERCIAL CENTER/CRESC

South Poinciana Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5075053
Active 2125 Cattle Dr, KISSIMMEE

$2,000,000

ACREAGE & UNREC

2125 Cattle Dr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5073546
Active 7442 Gathering Ct, KISSIMMEE

$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 1501 Sunset Pointe Pl, KISSIMMEE

$1,890,000

SUNSET POINTE

1501 Sunset Pointe Pl, KISSIMMEE

5 Beds 4 Baths 3,685 SqFt Single Family Residence MLS® # S5085644
Active North Hoagland Blvd, KISSIMMEE

$1,883,000

ACREAGE & UNREC

North Hoagland Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6085435
Active 2812 Sleeping Dragon Ln, KISSIMMEE

$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 1830 Kings Hwy, KISSIMMEE

$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 312 Auburn Ave, KISSIMMEE

$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 2261 Main Sail Cv, KISSIMMEE

$1,500,000

HIDDEN HARBOR

2261 Main Sail Cv, KISSIMMEE

4 Beds 5 Baths 6,258 SqFt Single Family Residence MLS® # O6101195
Active 2909 Fable St, KISSIMMEE

$1,500,000

STOREY LAKE PH 3

2909 Fable St, KISSIMMEE

8 Beds 5 Baths 4,303 SqFt Single Family Residence MLS® # O6088862
Active 50 Lakeview Dr, KISSIMMEE

$1,500,000

JOHNSON LILLIE RESUB

50 Lakeview Dr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6017163
Active Granada Blvd, KISSIMMEE

$1,500,000

TOHOP ESTATES

Granada Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S4856294
Active 1560 Turkey Ln, KISSIMMEE

$1,499,990

ACREAGE & UNREC

1560 Turkey Ln, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6070355
Active 1384 East Lakeshore Blvd, KISSIMMEE

$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 7616 Brookhurst Ln, KISSIMMEE

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

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