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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 3008 Parrot Head Pl, KISSIMMEE

$999,999

MARGARITAVILLE RESORT ORLANDO

3008 Parrot Head Pl, KISSIMMEE

3 Beds 4 Baths 1,818 SqFt Single Family Residence MLS® # S5091508
FEATURED
Active 7648 Wilmington Loop, KISSIMMEE

$995,000

ENCORE AT REUNION

7648 Wilmington Loop, KISSIMMEE

9 Beds 9 Baths 4,630 SqFt Single Family Residence MLS® # S5091283
FEATURED
Active 8983 Amelia Downs Tr, KISSIMMEE

$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 8579 La Isla Dr, KISSIMMEE

$599,950

EMERALD ISLAND RESORT

8579 La Isla Dr, KISSIMMEE

7 Beds 5 Baths 2,881 SqFt Single Family Residence MLS® # S5091701
FEATURED
Active 2190 Fleming Mist Pl, KISSIMMEE

$575,000

▼ $24,950 SOLARA RESORT

2190 Fleming Mist Pl, KISSIMMEE

5 Beds 5 Baths 2,283 SqFt Townhouse MLS® # S5085203
FEATURED
Active 945 Emerald Green Ct, KISSIMMEE

$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 3115 Yellow Lantana Ln, KISSIMMEE

$356,500

▼ $23,480 ENCANTADA

3115 Yellow Lantana Ln, KISSIMMEE

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

$356,500

▼ $23,480 ENCANTADA

3113 Yellow Lantana Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5084425
FEATURED
Active 2821 Almaton Loop 403, KISSIMMEE

$346,000

WINDSOR HILLS RESORT

2821 Almaton Loop 403, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Condominium MLS® # S5090589
FEATURED
Active 8589 Bay Lilly Loop, KISSIMMEE

$319,950

▼ $28,000 ENCANTADA

8589 Bay Lilly Loop, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5088854
FEATURED
Active 4704 Vero Beach Pl, KISSIMMEE

$310,000

▼ $23,333 TERRA VERDE VILLAS

4704 Vero Beach Pl, KISSIMMEE

3 Beds 3 Baths 1,286 SqFt Townhouse MLS® # S5084253
FEATURED
Active 9051 Treasure Trove Ln 108, KISSIMMEE

$225,000

CARIBE COVE

9051 Treasure Trove Ln 108, KISSIMMEE

2 Beds 2 Baths 1,445 SqFt Condo - Hotel MLS® # S5089968
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 3070 Gus Rd, KISSIMMEE

$5,000,000

ACREAGE & UNREC

3070 Gus Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6073505
Active 3555 Boggy Creek Rd, KISSIMMEE

$5,000,000

▲ $2,000,000 LOGANS RUN

3555 Boggy Creek Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6073331
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 3060 Gus Rd, KISSIMMEE

$3,500,000

ACREAGE & UNREC

3060 Gus Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6125360
New
Active East Irlo Bronson Mem Hwy, KISSIMMEE

$3,315,000

EMERALD LAKE COLONY UN #3

East Irlo Bronson Mem Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6143696
Active Lots 2 & 3 Sr 535 Rd, KISSIMMEE

$3,200,000

▲ $300,000 TRIANGLE PD

Lots 2 & 3 Sr 535 Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O5918414
Active 1010 Suhls Ln, KISSIMMEE

$3,150,000

▼ $100,000 ACREAGE & UNREC

1010 Suhls Ln, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6041484
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 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 4445 Austin Rd, KISSIMMEE

$2,500,000

ACREAGE & UNREC

4445 Austin Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O5979926
Active 906 Jack Nicklaus Ct, KISSIMMEE

$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 955 Jack Nicklaus Ct, KISSIMMEE

$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 1300 Grandview Blvd, KISSIMMEE

$2,300,000

REGAL POINT WEST

1300 Grandview Blvd, KISSIMMEE

5 Beds 6 Baths 6,176 SqFt Single Family Residence MLS® # G5072774
New
Active 8097 Surf St, KISSIMMEE

$1,950,000

ROLLING OAKS PH 6A

8097 Surf St, KISSIMMEE

8 Beds 11 Baths 4,092 SqFt Single Family Residence MLS® # O6139323
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 2221 West Martin St, KISSIMMEE

$1,900,000

2221 West Martin St, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6118616
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 7928 Jacks Club Ct, KISSIMMEE

$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 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 7924 Jacks Club Ct, KISSIMMEE

$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 1427 Fairview Cir, KISSIMMEE

$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 2409 Shanti Dr, KISSIMMEE

$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 2359 Rama Dr, KISSIMMEE

$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 312 Auburn Ave, KISSIMMEE

$1,500,000

REUNION WEST PH 4

312 Auburn Ave, KISSIMMEE

9 Beds 9 Baths 5,030 SqFt Single Family Residence MLS® # O6131665
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
New
Active 50 Lakeview Dr, KISSIMMEE

$1,400,000

JOHNSON LILLIE RESUB

50 Lakeview Dr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5091781
Active 8550 Sweetwater Tr, KISSIMMEE

$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 241 Falls Dr, KISSIMMEE

$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.

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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