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
ACREAGE & UNREC
W Irlo Bronson Memorial Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
Land
MLS® # S5085096
FEATURED
Active
$7,700,000
ACREAGE & UNREC
200 N Hoagland Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
Land
MLS® # S5085102
FEATURED
Active
$1,725,000
▼ $125,000
REUNION, BEARS DEN, REUNION WEST
7936 Jacks Club Ct, KISSIMMEE
6
Beds
7
Baths
4,588 SqFt
Residential
Single Family Residence
MLS® # S5144037
FEATURED
Active
$899,999
BELLAVIDA RESORT
262 Marcello Blvd, KISSIMMEE
12
Beds
12
Baths
4,762 SqFt
Residential
Single Family Residence
MLS® # S5146865
FEATURED
Active
$795,000
▼ $20,000
SOLARA RESORT
1636 Nassau Point Tr, KISSIMMEE
9
Beds
7
Baths
4,828 SqFt
Residential
Single Family Residence
MLS® # S5138722
FEATURED
Active
$759,900
▼ $15,100
FORMOSA GARDENS
7950 Sea Pearl Cir, KISSIMMEE
5
Beds
4
Baths
3,676 SqFt
Residential
Single Family Residence
MLS® # S5150770
FEATURED
Active
$724,500
MARGARITAVILLE RESORT, ROLLING OAKS
8019 Knee Deep Rd, KISSIMMEE
5
Beds
4
Baths
1,908 SqFt
Residential
Single Family Residence
MLS® # S5149245
FEATURED
Active
$719,950
ENCORE AT REUNION, REUNION WEST
350 Pendant Ct, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Residential
Single Family Residence
MLS® # S5120062
FEATURED
Active
$699,999
ENCORE AT REUNION, REUNION WEST
551 Lasso Dr, KISSIMMEE
8
Beds
7
Baths
3,401 SqFt
Residential
Single Family Residence
MLS® # S5128532
FEATURED
Active
$699,999
ENCORE AT REUNION, REUNION WEST
7527 Marker Ave, KISSIMMEE
8
Beds
6
Baths
3,612 SqFt
Residential
Single Family Residence
MLS® # S5126948
New
FEATURED
Active
$690,000
BELLAVIDA RESORT
302 Marcello Blvd, KISSIMMEE
8
Beds
6
Baths
3,805 SqFt
Residential
Single Family Residence
MLS® # S5155134
FEATURED
Active
$669,999
SUNSET WALK HOTEL, EMBASSY SUITES AT SUNSET WALK
3151 Sunset Walk Drive 1316 And 1318, KISSIMMEE
2
Beds
2
Baths
1,500 SqFt
Residential
Condo - Hotel
MLS® # S5152204
FEATURED
Active
$669,999
CHAMPIONSGATE, STONEYBROOK SOUTH
9046 Stinger Dr, DAVENPORT
9
Beds
5
Baths
3,909 SqFt
Residential
Single Family Residence
MLS® # S5144582
FEATURED
Active
$669,456
ENCORE AT REUNION, REUNION WEST
7541 Marker Ave, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Residential
Single Family Residence
MLS® # S5128347
FEATURED
Active
$669,123
ENCORE AT REUNION, REUNION WEST
331 Pendant Ct, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Residential
Single Family Residence
MLS® # S5128341
New
FEATURED
Active
$659,000
ENCORE AT REUNION, REUNION WEST
341 Pendant Ct, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Residential
Single Family Residence
MLS® # S5154995
FEATURED
Active
$639,000
▼ $10,000
AVELLINO
2331 Avellino Ave, ST CLOUD
5
Beds
3
Baths
3,757 SqFt
Residential
Single Family Residence
MLS® # S5152586
FEATURED
Active
$629,000
▼ $20,000
ENCORE AT REUNION, REUNION WEST
7613 Brookhurst Ln, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Residential
Single Family Residence
MLS® # S5128335
FEATURED
Active
$615,000
WINDSOR HILLS
2648 Daulby St, KISSIMMEE
6
Beds
4
Baths
2,469 SqFt
Residential
Single Family Residence
MLS® # S5153001
FEATURED
Active
$599,999
▼ $20,001
CHAMPIONSGATE, STONEYBROOK SOUTH
9038 Stinger Dr, DAVENPORT
6
Beds
6
Baths
3,339 SqFt
Residential
Single Family Residence
MLS® # S5147802
FEATURED
Active
$549,000
▼ $50,990
CHAMPIONSGATE, STONEYBROOK
661 Drop Shot Dr, DAVENPORT
5
Beds
5
Baths
3,081 SqFt
Residential
Single Family Residence
MLS® # S5128828
FEATURED
Active
$535,000
ENCORE AT REUNION, REUNION WEST
276 Southfield St, KISSIMMEE
4
Beds
3
Baths
2,363 SqFt
Residential
Single Family Residence
MLS® # S5150128
FEATURED
Active
$529,999
EMERALD ISLAND RESORT
8550 Sunrise Key Dr, KISSIMMEE
7
Beds
5
Baths
2,881 SqFt
Residential
Single Family Residence
MLS® # S5148879
FEATURED
Active
$525,000
INDIAN CREEK
2685 Oneida Loop, KISSIMMEE
5
Beds
4
Baths
2,136 SqFt
Residential
Single Family Residence
MLS® # S5128631
FEATURED
Active
$515,000
▼ $5,000
EMERALD ISLAND RESORT
2694 La Isla Ct, KISSIMMEE
5
Beds
3
Baths
2,317 SqFt
Residential
Single Family Residence
MLS® # S5149891
FEATURED
Active
$479,000
PARADISE PALMS RESORT
8965 Cuban Palm Rd, KISSIMMEE
6
Beds
5
Baths
3,291 SqFt
Residential
Single Family Residence
MLS® # S5147422
FEATURED
Active
$465,000
▼ $10,000
TERRA VERDE
4661 Golden Beach Ct, KISSIMMEE
5
Beds
3
Baths
2,269 SqFt
Residential
Single Family Residence
MLS® # S5142740
FEATURED
Active
$464,900
STOREY LAKE RESORT
4805 Brier Rose Ln, KISSIMMEE
4
Beds
3
Baths
1,914 SqFt
Residential
Townhouse
MLS® # S5132665
FEATURED
Active
$449,999
▼ $50,000
EMBASSY SUITES, SUNSET WALK HOTEL
3151 Sunset Walk Dr 1108, KISSIMMEE
2
Beds
2
Baths
1,029 SqFt
Residential
Condo - Hotel
MLS® # S5132617
FEATURED
Active
$444,000
▼ $20,000
WINDSOR AT WESTSIDE
2427 Dubai St, KISSIMMEE
5
Beds
5
Baths
2,265 SqFt
Residential
Townhouse
MLS® # S5123971
FEATURED
Active
$434,999
▼ $10,001
WINDSOR AT WESTSIDE
1909 Majorca Dr, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Residential
Townhouse
MLS® # S5149758
FEATURED
Active
$418,999
ENCANTADA
3015 Yellow Lantana Ln, KISSIMMEE
4
Beds
3
Baths
1,636 SqFt
Residential
Townhouse
MLS® # S5126724
FEATURED
Active
$410,000
REUNION RESORT, CENTRE COURT RIDGE
1356 Centre Court Ridge Dr 303, KISSIMMEE
3
Beds
3
Baths
1,590 SqFt
Residential
Condominium
MLS® # S5153768
FEATURED
Active
$399,999
MARGARITAVILLE RESORT
8081 Knee Deep Rd, KISSIMMEE
2
Beds
2
Baths
1,188 SqFt
Residential
Single Family Residence
MLS® # S5151963
FEATURED
Active
$399,000
MARGARITAVILLE, ROLLING OAKS
3071 Key Lime Loop, KISSIMMEE
2
Beds
3
Baths
1,217 SqFt
Residential
Single Family Residence
MLS® # S5153366
FEATURED
Active
$399,000
▼ $50,000
SUNSET WALK HOTEL, EMBASSY SUITES
3151 Sunset Walk Dr 1214, KISSIMMEE
2
Beds
2
Baths
1,163 SqFt
Residential
Condo - Hotel
MLS® # S5141552
FEATURED
Active
$377,900
▼ $71,100
SUNSET WALK HOTEL, EMBASSY SUITES
8070 Unwind Way 5416, KISSIMMEE
2
Beds
2
Baths
1,029 SqFt
Residential
Condo - Hotel
MLS® # S5141228
FEATURED
Active
$359,999
▼ $10,000
MARGARITAVILLE, ROLLING OAKS
2916 On The Rocks Pt, KISSIMMEE
3
Beds
3
Baths
1,545 SqFt
Residential
Townhouse
MLS® # S5149980
FEATURED
Active
$349,900
WINDSOR HILLS, VENTURA AT WINDSOR HILLS
2821 Almaton Loop 203, KISSIMMEE
3
Beds
2
Baths
1,246 SqFt
Residential
Condominium
MLS® # S5147977
FEATURED
Active
$349,000
▼ $50,999
SUNSET WALK HOTEL, EMBASSY SUITES
8061 Vacation Ave 2508, KISSIMMEE
2
Beds
2
Baths
1,029 SqFt
Residential
Condo - Hotel
MLS® # S5144118
FEATURED
Active
$344,000
▼ $5,000
PARADISE PALMS RESORT
8957 Sugar Palm Rd, KISSIMMEE
4
Beds
3
Baths
1,902 SqFt
Residential
Townhouse
MLS® # S5142216
FEATURED
Active
$340,000
▼ $5,000
SUNSET WALK HOTEL, EMBASSY SUITES
8061 Vacation Ave 2510, KISSIMMEE
2
Beds
2
Baths
1,029 SqFt
Residential
Condo - Hotel
MLS® # S5144575
FEATURED
Active
$339,000
▼ $31,000
ENCANTADA
3083 Yellow Lantana Ln, KISSIMMEE
4
Beds
3
Baths
1,340 SqFt
Residential
Townhouse
MLS® # S5116892
FEATURED
Active
$330,000
REGAL OAKS
2714 Bushman Dr, KISSIMMEE
4
Beds
4
Baths
1,852 SqFt
Residential
Townhouse
MLS® # S5151642
FEATURED
Active
$319,500
▼ $12,500
WEST LUCAYA VILLAGE
3222 Cupid Pl, KISSIMMEE
4
Beds
3
Baths
1,694 SqFt
Residential
Townhouse
MLS® # S5141535
FEATURED
Active
$315,000
▲ $35,050
WEST LUCAYA VILLAGE
3240 Cupid Pl, KISSIMMEE
4
Beds
3
Baths
1,694 SqFt
Residential
Townhouse
MLS® # S5152792
FEATURED
Active
$310,000
VENETIAN BAY
2200 San Zanobi Dr 108, KISSIMMEE
4
Beds
3
Baths
1,470 SqFt
Residential
Condominium
MLS® # S5102991
FEATURED
Active
$299,999
CHAMPIONSGATE
1153 Drop Ln, DAVENPORT
2
Beds
2
Baths
1,388 SqFt
Residential
Condominium
MLS® # S5132169
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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