Osceola County Vacation Homes
County: Orange County | Osceola County | Polk County | Lake County
Osceola County Resorts: Bella Trae - Bella Vida Resort - Caribe Cove Resort - ChampionsGate - Embassy Suites At Sunset Walk - Emerald Island Resort - Encantada - Encore Club at Reunion - Fiesta Key - Formosa Valley - Lake Berkley - Lucaya Village - Magic Village - Margaritaville Resort Orlando - Melia Orlando Celebration - Paradise Palms - Regal Oaks - Reunion Resort - Solara Resort - Storey Lake Resort - Summerville Resort - Terra Verde Resort - Tuscana - Venetian Bay - Veranda Palms - Villas At Seven Dwarfs Lane - Windsor Hills Resort - Windsor Palms Resort
When you’re looking for Orlando vacation homes, one of the more popular areas to consider is Osceola County. This 1,500 square mile area serves as the south/central boundary of Central Florida. The county seat is Kissimmee, which is popular with tourists because of its proximity to the major theme parks, including Walt Disney World.
Osceola County was named for a Seminole warrior leader, who led several small, successful raids against the U.S. Army in the 1800’s. The county was formed in 1887 from portions of Orange and Brevard counties, and was a transportation hub in the late 19th century for riverboats and railroad. It later transformed into a cattle, sugar and lumber-based economy.
Check out the Osceola County Vacation Homes for Sale available below, or learn more about this popular area for Florida holiday communities.
Search Osceola County Real Estate Listings
FEATURED
Active
$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
$7,700,000
▼ $12,300,000
ACREAGE & UNREC
200 N Hoagland Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5085102
FEATURED
Active
$1,555,555
MARGARITAVILLE, ROLLING OAKS
8161 Surf St, KISSIMMEE
5
Beds
5
Baths
3,578 SqFt
Single Family Residence
MLS® # S5108628
FEATURED
Active
$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
$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
$874,950
▼ $24,000
REUNION RESORT
7714 Excitement Dr, REUNION
5
Beds
5
Baths
3,614 SqFt
Single Family Residence
MLS® # S5107884
FEATURED
Active
$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
$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
$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
$729,950
▼ $120,000
ENCORE AT REUNION, REUNION
161 Lasso Dr, KISSIMMEE
9
Beds
8
Baths
4,066 SqFt
Single Family Residence
MLS® # S5104706
FEATURED
Active
$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
$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
$645,000
MARGARITAVILLE, ROLLING OAKS
2918 Salted Rim Rd, KISSIMMEE
4
Beds
3
Baths
1,410 SqFt
Single Family Residence
MLS® # S5106497
FEATURED
Active
$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
$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
$595,000
MARGARITAVILLE, ROLLING OAKS
3184 Caribbean Soul Dr, KISSIMMEE
4
Beds
3
Baths
1,712 SqFt
Townhouse
MLS® # S5103875
FEATURED
Active
$579,950
WINDSOR AT WESTSIDE
8937 Rhodes St, KISSIMMEE
5
Beds
6
Baths
2,622 SqFt
Single Family Residence
MLS® # S5106825
FEATURED
Active
$559,950
▼ $15,000
EMERALD ISLAND RESORT
8415 Secret Key Cv, KISSIMMEE
8
Beds
5
Baths
2,914 SqFt
Single Family Residence
MLS® # S5101311
FEATURED
Active
$539,500
▲ $34,510
SOLARA RESORT
2190 Fleming Mist Pl, KISSIMMEE
5
Beds
5
Baths
2,283 SqFt
Townhouse
MLS® # S5085203
FEATURED
Active
$499,995
EMERALD ISLAND RESORT
2776 Lido Key Dr, KISSIMMEE
5
Beds
4
Baths
2,317 SqFt
Single Family Residence
MLS® # S5107387
FEATURED
Active
$499,950
MARGARITAVILLE, ROLLING OAKS
3044 Salted Rim Rd, KISSIMMEE
2
Beds
3
Baths
1,305 SqFt
Single Family Residence
MLS® # S5105327
FEATURED
Active
$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
$464,950
▼ $50
WINDSOR AT WESTSIDE
8847 Geneve Ct, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5097326
FEATURED
Active
$449,950
INDIAN CREEK
2665 Oneida Loop, KISSIMMEE
4
Beds
3
Baths
1,791 SqFt
Single Family Residence
MLS® # S5108926
FEATURED
Active
$449,950
REUNION FAIRWAYS, REUNION
7920 Draw St, REUNION
3
Beds
3
Baths
1,704 SqFt
Townhouse
MLS® # S5103314
FEATURED
Active
$435,000
WINDSOR HILLS
7662 Fitzclarence St, KISSIMMEE
3
Beds
3
Baths
1,440 SqFt
Townhouse
MLS® # S5098222
FEATURED
Active
$435,000
EAGLE POINTE
4636 Eagle Peak Dr, KISSIMMEE
4
Beds
2
Baths
1,822 SqFt
Single Family Residence
MLS® # S5103835
FEATURED
Active
$424,950
PARADISE PALMS RESORT
8934 Majesty Palm Rd, KISSIMMEE
5
Beds
4
Baths
2,024 SqFt
Townhouse
MLS® # S5108455
FEATURED
Active
$399,950
CHAMPIONS POINTE, CHAMPIONS GATE, CHAMPIONSGATE
457 Bogey Dr, DAVENPORT
3
Beds
3
Baths
1,988 SqFt
Townhouse
MLS® # S5098974
New
FEATURED
Active
$384,950
WINDSOR HILLS, VENTURA AT WINDSOR HILLS
7650 Comrow St 305, KISSIMMEE
3
Beds
2
Baths
1,410 SqFt
Condominium
MLS® # S5109023
FEATURED
Active
$379,000
REUNION, VILLAS AT REUNION SQUARE
7613 Cabana Ct 304, REUNION
3
Beds
3
Baths
1,755 SqFt
Condominium
MLS® # S5108294
FEATURED
Active
$349,950
INDIAN WELLS
3189 Bear Path, KISSIMMEE
3
Beds
2
Baths
1,377 SqFt
Single Family Residence
MLS® # S5107403
FEATURED
Active
$349,950
ENCANTADA
3189 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5108427
FEATURED
Active
$344,900
WINDSOR HILLS RESORT
2821 Almaton Loop 401, KISSIMMEE
3
Beds
2
Baths
1,246 SqFt
Condominium
MLS® # S5106674
FEATURED
Active
$335,000
REGAL OAKS
2614 Roadster Ln, KISSIMMEE
2
Beds
3
Baths
1,350 SqFt
Townhouse
MLS® # S5105229
FEATURED
Active
$329,000
CORAL CAY RESORT
2327 Caravelle Cir, KISSIMMEE
4
Beds
3
Baths
1,636 SqFt
Townhouse
MLS® # S5108638
FEATURED
Active
$320,000
▼ $29,950
CORAL CAY RESORT
2374 Caravelle Cir, KISSIMMEE
5
Beds
3
Baths
1,704 SqFt
Townhouse
MLS® # S5099612
FEATURED
Active
$310,000
VENETIAN BAY
2200 San Zanobi Dr 108, KISSIMMEE
4
Beds
3
Baths
1,470 SqFt
Condominium
MLS® # S5102991
FEATURED
Active
$286,800
WINDSOR PALMS
2308 Silver Palm Dr 204, KISSIMMEE
3
Beds
2
Baths
1,402 SqFt
Condominium
MLS® # S5104897
FEATURED
Active
$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
$279,950
ENCANTADA
3002 Bird Of Paradise Ln, KISSIMMEE
2
Beds
3
Baths
1,161 SqFt
Townhouse
MLS® # S5103141
FEATURED
Active
$269,950
SWEETWATER CLUB
2472 Sweetwater Club Cir 118, KISSIMMEE
3
Beds
2
Baths
1,220 SqFt
Condominium
MLS® # S5108916
FEATURED
Active
$264,900
▼ $12,100
ENCANTADA
3018 Red Ginger Rd, KISSIMMEE
2
Beds
3
Baths
1,161 SqFt
Townhouse
MLS® # S5103647
FEATURED
Active
$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
FEATURED
Active
$238,700
▼ $6,100
TUSCANA
1301 Tuscan Ter 9104, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condominium
MLS® # S5095966
FEATURED
Active
$234,700
▼ $10,100
TUSCANA RESORT
8000 Tuscany Way 4308, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condominium
MLS® # S5106218
FEATURED
Active
$215,000
TUSCANA
1371 Tuscan Ter 6108, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condominium
MLS® # S5106761
FEATURED
Active
$209,950
▼ $5,000
TUSCANA
8010 Tuscany Way 3103, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5101225
Living in Osceola County
The area became well-known as a tourist destination after Walt Disney World opened in the 1970s. Today, there are plenty of attractions to keep visitors amused, such as Old Town which features a family fun track, arcade, shops, restaurants, and gift shops.
One of the appeals of owning a second home in Osceola County is that the area is home to the Kissimmee Chain-of-Lakes, which includes some of Florida’s largest and finest fishing and recreational attractions like Lake Tohopekaliga. World renowned for bass fishing, Lake Toho, as it’s known to locals, is also a popular place to take an airboat ride to view the Florida wilderness and headwaters that feed the Everglades.
Osceola County Real Estate Market
Vacation home buyers have a large choice of home and community types to choose from in Osceola County. There are gated communities for extra privacy, as well as resort and waterfront communities. Vacation homes available for sale include luxurious single family homes and villas, condos and townhouses.
For example, you’ll find beautiful Kissimmee vacation homes for sale at the Reunion Resort. This amazing resort is the only one in the world that features three signature golf courses designed by the sport’s greatest legends: Jack Nicklaus, Arnold Palmer and Tom Watson. The resort also includes its own water park with a lazy river and twisting water slides, as well as additional swimming pools, Jacuzzis and poolside dining.
If you have any questions about the homes for sale in Osceola County, contact a Team Donovan agent today at 407-705-2616. We look forward to helping you select your ideal Orlando vacation home.
Are you interested in purchasing vacation property in Osceola County? We encourage you to or give us a call at 407-705-2616. We'd be thrilled to help you find yourself a beautiful Orlando vacation home near Disney World!
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