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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
New FEATURED
Active 8161 Surf St, KISSIMMEE

$1,555,555

MARGARITAVILLE, ROLLING OAKS

8161 Surf St, KISSIMMEE

5 Beds 5 Baths 3,578 SqFt Single Family Residence MLS® # S5108628
FEATURED
Active 2711 Bookmark Dr, KISSIMMEE

$919,950

STOREY LAKE, COVE AT STOREY LAKE

2711 Bookmark Dr, KISSIMMEE

9 Beds 5 Baths 4,289 SqFt Single Family Residence MLS® # S5106748
FEATURED
Active 520 Burma St, KISSIMMEE

$899,000

▼ $212,111 ENCORE AT REUNION

520 Burma St, KISSIMMEE

9 Beds 9 Baths 4,630 SqFt Single Family Residence MLS® # S5098246
FEATURED
Active 161 Lasso Dr, KISSIMMEE

$849,950

ENCORE AT REUNION, REUNION

161 Lasso Dr, KISSIMMEE

9 Beds 8 Baths 4,066 SqFt Single Family Residence MLS® # S5104706
FEATURED
Active 7658 Wilmington Loop, KISSIMMEE

$828,949

▼ $1 ENCORE AT REUNION, REUNION RESORT

7658 Wilmington Loop, KISSIMMEE

11 Beds 10 Baths 4,707 SqFt Single Family Residence MLS® # S5107040
FEATURED
Active 8983 Amelia Downs Tr, KISSIMMEE

$824,950

▼ $50,000 SOLARA RESORT

8983 Amelia Downs Tr, KISSIMMEE

9 Beds 7 Baths 4,363 SqFt Single Family Residence MLS® # S5086743
FEATURED
Active 4358 Phrase St, KISSIMMEE

$809,950

▼ $50,000 STOREY LAKE, COVE AT STOREY LAKE

4358 Phrase St, KISSIMMEE

6 Beds 5 Baths 3,291 SqFt Single Family Residence MLS® # S5106294
FEATURED
Active 7562 Marker Ave, KISSIMMEE

$699,900

▼ $15,000 ENCORE AT REUNION

7562 Marker Ave, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Single Family Residence MLS® # S5100653
FEATURED
Active 8812 Macapa Dr, KISSIMMEE

$680,000

▼ $49,950 WINDSOR AT WESTSIDE

8812 Macapa Dr, KISSIMMEE

8 Beds 6 Baths 4,041 SqFt Single Family Residence MLS® # S5102453
FEATURED
Active 2918 Salted Rim Rd, KISSIMMEE

$645,000

MARGARITAVILLE, ROLLING OAKS

2918 Salted Rim Rd, KISSIMMEE

4 Beds 3 Baths 1,410 SqFt Single Family Residence MLS® # S5106497
FEATURED
Active 220 Pendant Ct, KISSIMMEE

$629,950

▼ $18,850 ENCORE AT REUNION

220 Pendant Ct, KISSIMMEE

6 Beds 7 Baths 3,317 SqFt Single Family Residence MLS® # S5099537
FEATURED
Active 7953 Heritage Entrance Blvd, KISSIMMEE

$599,950

▼ $25,000 ROLLING HILLS, ROLLING HILLS ESTATES

7953 Heritage Entrance Blvd, KISSIMMEE

5 Beds 4 Baths 2,618 SqFt Single Family Residence MLS® # S5106283
FEATURED
Active 3184 Caribbean Soul Dr, KISSIMMEE

$595,000

MARGARITAVILLE, ROLLING OAKS

3184 Caribbean Soul Dr, KISSIMMEE

4 Beds 3 Baths 1,712 SqFt Townhouse MLS® # S5103875
FEATURED
Active 8937 Rhodes St, KISSIMMEE

$579,950

WINDSOR AT WESTSIDE

8937 Rhodes St, KISSIMMEE

5 Beds 6 Baths 2,622 SqFt Single Family Residence MLS® # S5106825
FEATURED
Active 8415 Secret Key Cv, KISSIMMEE

$574,950

▼ $25,000 EMERALD ISLAND RESORT

8415 Secret Key Cv, KISSIMMEE

8 Beds 5 Baths 2,914 SqFt Single Family Residence MLS® # S5101311
FEATURED
Active 8035 Acadia Estates Ct, KISSIMMEE

$556,950

▼ $13,000 ACADIA ESTATES, WYNDHAM POINTE

8035 Acadia Estates Ct, KISSIMMEE

6 Beds 5 Baths 2,769 SqFt Single Family Residence MLS® # S5098360
FEATURED
Active 2190 Fleming Mist Pl, KISSIMMEE

$539,500

▲ $34,510 SOLARA RESORT

2190 Fleming Mist Pl, KISSIMMEE

5 Beds 5 Baths 2,283 SqFt Townhouse MLS® # S5085203
FEATURED
Active 2776 Lido Key Dr, KISSIMMEE

$499,995

EMERALD ISLAND RESORT

2776 Lido Key Dr, KISSIMMEE

5 Beds 4 Baths 2,317 SqFt Single Family Residence MLS® # S5107387
FEATURED
Active 3044 Salted Rim Rd, KISSIMMEE

$499,950

MARGARITAVILLE, ROLLING OAKS

3044 Salted Rim Rd, KISSIMMEE

2 Beds 3 Baths 1,305 SqFt Single Family Residence MLS® # S5105327
FEATURED
Active 155 Barefoot Beach Way, KISSIMMEE

$465,000

▼ $34,950 TERRA VERDE

155 Barefoot Beach Way, KISSIMMEE

4 Beds 2 Baths 1,940 SqFt Single Family Residence MLS® # S5105388
FEATURED
Active 8847 Geneve Ct, KISSIMMEE

$464,950

▼ $50 WINDSOR AT WESTSIDE

8847 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5097326
New FEATURED
Active 2665 Oneida Loop, KISSIMMEE

$449,950

INDIAN CREEK

2665 Oneida Loop, KISSIMMEE

4 Beds 3 Baths 1,791 SqFt Single Family Residence MLS® # S5108926
FEATURED
Active 7662 Fitzclarence St, KISSIMMEE

$435,000

WINDSOR HILLS

7662 Fitzclarence St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5098222
FEATURED
Active 4636 Eagle Peak Dr, KISSIMMEE

$435,000

EAGLE POINTE

4636 Eagle Peak Dr, KISSIMMEE

4 Beds 2 Baths 1,822 SqFt Single Family Residence MLS® # S5103835
FEATURED
Active 8934 Majesty Palm Rd, KISSIMMEE

$424,950

PARADISE PALMS RESORT

8934 Majesty Palm Rd, KISSIMMEE

5 Beds 4 Baths 2,024 SqFt Townhouse MLS® # S5108455
FEATURED
Active 3189 Bear Path, KISSIMMEE

$349,950

INDIAN WELLS

3189 Bear Path, KISSIMMEE

3 Beds 2 Baths 1,377 SqFt Single Family Residence MLS® # S5107403
FEATURED
Active 3189 Yellow Lantana Ln, KISSIMMEE

$349,950

ENCANTADA

3189 Yellow Lantana Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5108427
FEATURED
Active 2821 Almaton Loop 401, KISSIMMEE

$344,900

WINDSOR HILLS RESORT

2821 Almaton Loop 401, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Condominium MLS® # S5106674
FEATURED
Active 2614 Roadster Ln, KISSIMMEE

$335,000

REGAL OAKS

2614 Roadster Ln, KISSIMMEE

2 Beds 3 Baths 1,350 SqFt Townhouse MLS® # S5105229
New FEATURED
Active 2327 Caravelle Cir, KISSIMMEE

$329,000

CORAL CAY RESORT

2327 Caravelle Cir, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Townhouse MLS® # S5108638
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 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 2308 Silver Palm Dr 204, KISSIMMEE

$286,800

WINDSOR PALMS

2308 Silver Palm Dr 204, KISSIMMEE

3 Beds 2 Baths 1,402 SqFt Condominium MLS® # S5104897
FEATURED
Active 2609 Gala Rd N 103, KISSIMMEE

$279,950

VILLAS AT SEVEN DWARFS LANE

2609 Gala Rd N 103, KISSIMMEE

3 Beds 2 Baths 1,296 SqFt Condominium MLS® # S5102734
FEATURED
Active 3002 Bird Of Paradise Ln, KISSIMMEE

$279,950

ENCANTADA

3002 Bird Of Paradise Ln, KISSIMMEE

2 Beds 3 Baths 1,161 SqFt Townhouse MLS® # S5103141
FEATURED
Active 3018 Red Ginger Rd, KISSIMMEE

$277,000

▼ $12,000 ENCANTADA

3018 Red Ginger Rd, KISSIMMEE

2 Beds 3 Baths 1,161 SqFt Townhouse MLS® # S5103647
New FEATURED
Active 2472 Sweetwater Club Cir 118, KISSIMMEE

$269,950

SWEETWATER CLUB

2472 Sweetwater Club Cir 118, KISSIMMEE

3 Beds 2 Baths 1,220 SqFt Condominium MLS® # S5108916
FEATURED
Active 2260 San Vital Dr 106, KISSIMMEE

$259,000

▼ $9,000 VENETIAN BAY, VENETIAN BAY VILLAGES

2260 San Vital Dr 106, KISSIMMEE

3 Beds 2 Baths 1,296 SqFt Condominium MLS® # S5103160
Active 4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

$7,894,000

▼ $500 ACREAGE & UNREC

4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6158900
Active Simpson Rd, KISSIMMEE

$6,250,000

Simpson Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5103046
Active Twilight Tr, KISSIMMEE

$4,885,000

▼ $615,000 PLEASANT HILL TRAILS UNIT 01

Twilight Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # L4943863
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 2225 East Irlon Bronson E, KISSIMMEE

$4,300,000

2225 East Irlon Bronson E, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6211605
Active 4050 Brighton Lakes Blvd, KISSIMMEE

$4,000,000

BRIGHTON LAKES PH 1

4050 Brighton Lakes Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6204727
Active 43 East Lake Shore Blvd, KISSIMMEE

$3,500,000

FLORIDA FRUIT BELT SALES CO 1

43 East Lake Shore Blvd, KISSIMMEE

6 Beds 8 Baths 6,946 SqFt Single Family Residence MLS® # S5106494
Active 3060 Gus Rd, KISSIMMEE

$3,500,000

ACREAGE & UNREC

3060 Gus Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6125360

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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