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
$1,350,000
ENCORE AT REUNION, REUNION WEST
7665 Fairfax Dr, KISSIMMEE
11
Beds
13
Baths
5,496 SqFt
Single Family Residence
MLS® # S5123395
FEATURED
Active
$988,999
▼ $11,000
ENCORE AT REUNION, REUNION RESORT
7639 Wilmington Loop, KISSIMMEE
11
Beds
10
Baths
4,707 SqFt
Single Family Residence
MLS® # S5116680
FEATURED
Active
$825,000
ENCORE AT REUNION, REUNION WEST
7527 Marker Ave, KISSIMMEE
8
Beds
6
Baths
3,612 SqFt
Single Family Residence
MLS® # S5126948
FEATURED
Active
$719,950
ENCORE AT REUNION, REUNION WEST
561 Lasso Dr, KISSIMMEE
8
Beds
7
Baths
3,401 SqFt
Single Family Residence
MLS® # S5120195
FEATURED
Active
$719,950
ENCORE AT REUNION, REUNION WEST
350 Pendant Ct, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5120062
FEATURED
Active
$700,000
SPECTRUM AT REUNION, REUNION
7740 Sandy Ridge Dr 236, REUNION
5
Beds
5
Baths
2,630 SqFt
Condominium
MLS® # S5126016
FEATURED
Active
$699,999
ENCORE AT REUNION, REUNION WEST
551 Lasso Dr, KISSIMMEE
8
Beds
7
Baths
3,401 SqFt
Single Family Residence
MLS® # S5128532
FEATURED
Active
$675,000
WINDSOR AT WESTSIDE
8953 Zurich Ln, KISSIMMEE
7
Beds
6
Baths
3,314 SqFt
Single Family Residence
MLS® # S5118295
FEATURED
Active
$675,000
EMERALD ISLAND RESORT
8571 La Isla Dr, KISSIMMEE
7
Beds
6
Baths
3,599 SqFt
Single Family Residence
MLS® # S5126510
FEATURED
Active
$669,999
WINDSOR HILLS
7751 Tosteth St, KISSIMMEE
6
Beds
4
Baths
2,812 SqFt
Single Family Residence
MLS® # S5128304
FEATURED
Active
$669,789
ENCORE AT REUNION, REUNION WEST
7613 Brookhurst Ln, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5128335
FEATURED
Active
$669,456
ENCORE AT REUNION, REUNION WEST
7541 Marker Ave, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
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
Single Family Residence
MLS® # S5128341
FEATURED
Active
$639,950
▼ $35,050
REUNION
7412 Soiree Way, REUNION
5
Beds
4
Baths
2,764 SqFt
Single Family Residence
MLS® # S5122099
FEATURED
Active
$629,999
▼ $30,001
SOLARA RESORT
1800 Tropical Palms Cir, KISSIMMEE
5
Beds
5
Baths
2,294 SqFt
Townhouse
MLS® # S5121304
FEATURED
Active
$624,999
▼ $24,951
ENCORE AT REUNION, REUNION WEST
430 Novi Path, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5120422
FEATURED
Active
$599,999
ENCORE AT REUNION, REUNION WEST
341 Lasso Dr, KISSIMMEE
6
Beds
6
Baths
2,936 SqFt
Single Family Residence
MLS® # S5127732
FEATURED
Active
$599,999
MONTEGO BAY
2561 Montego Bay Blvd, KISSIMMEE
4
Beds
4
Baths
2,764 SqFt
Single Family Residence
MLS® # S5128315
FEATURED
Active
$599,990
CHAMPIONSGATE, STONEYBROOK
661 Drop Shot Dr, DAVENPORT
5
Beds
5
Baths
3,081 SqFt
Single Family Residence
MLS® # S5128828
FEATURED
Active
$598,000
WINDSOR AT WESTSIDE
8897 Rhodes St, KISSIMMEE
6
Beds
5
Baths
3,142 SqFt
Single Family Residence
MLS® # S5128935
FEATURED
Active
$575,000
▼ $24,999
STOREY LAKE, COVE AT STOREY LAKE
2569 Reading Tr, KISSIMMEE
4
Beds
3
Baths
2,168 SqFt
Townhouse
MLS® # S5122098
FEATURED
Active
$549,950
WINDSOR HILLS
7719 Comrow St, KISSIMMEE
4
Beds
4
Baths
1,824 SqFt
Single Family Residence
MLS® # S5124561
FEATURED
Active
$548,999
▼ $16,001
CHAMPIONSGATE, STONEYBROOK SOUTH
1424 Moon Valley Dr, DAVENPORT
5
Beds
5
Baths
2,842 SqFt
Single Family Residence
MLS® # S5123965
FEATURED
Active
$540,000
▼ $10,000
ENCORE AT REUNION, REUNION WEST
301 Pendant Ct, KISSIMMEE
5
Beds
5
Baths
2,570 SqFt
Single Family Residence
MLS® # S5121431
FEATURED
Active
$539,950
▼ $10,000
ENCORE AT REUNION, REUNION RESORT
280 Pendant Ct, KISSIMMEE
5
Beds
5
Baths
2,570 SqFt
Single Family Residence
MLS® # S5112064
FEATURED
Active
$529,950
▼ $20,000
MARGARITAVILLE, ROLLING OAKS
8012 Lost Shaker Ln, KISSIMMEE
4
Beds
4
Baths
1,850 SqFt
Single Family Residence
MLS® # S5121104
FEATURED
Active
$525,000
INDIAN CREEK
2685 Oneida Loop, KISSIMMEE
5
Beds
4
Baths
2,136 SqFt
Single Family Residence
MLS® # S5128631
FEATURED
Active
$499,999
TERRA VERDE RESORT
195 Hideaway Beach Ln, KISSIMMEE
6
Beds
6
Baths
2,834 SqFt
Single Family Residence
MLS® # S5129129
FEATURED
Active
$499,999
▼ $15,516
EMERALD ISLAND RESORT
8614 La Isla Dr, KISSIMMEE
5
Beds
4
Baths
2,317 SqFt
Single Family Residence
MLS® # S5119558
FEATURED
Active
$499,950
WINDSOR AT WESTSIDE
8886 Geneve Ct, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5119924
FEATURED
Active
$499,000
▼ $96,000
MARGARITAVILLE, ROLLING OAKS
3184 Caribbean Soul Dr, KISSIMMEE
4
Beds
3
Baths
1,712 SqFt
Townhouse
MLS® # S5103875
FEATURED
Active
$489,980
STOREY LAKE RESORT
4981 Windermere Ave, KISSIMMEE
4
Beds
3
Baths
1,914 SqFt
Townhouse
MLS® # S5128849
FEATURED
Active
$489,000
SUNSET LAKES
2993 Sunset Vista Blvd, KISSIMMEE
4
Beds
3
Baths
1,700 SqFt
Single Family Residence
MLS® # S5123939
FEATURED
Active
$479,950
▼ $10,000
WINDSOR AT WESTSIDE
2427 Dubai St, KISSIMMEE
5
Beds
5
Baths
2,265 SqFt
Townhouse
MLS® # S5123971
FEATURED
Active
$479,900
CHAMPIONSGATE, STONEYBROOK
8947 Stinger Dr, DAVENPORT
5
Beds
4
Baths
2,072 SqFt
Townhouse
MLS® # S5128773
FEATURED
Active
$474,950
CUMBRIAN LAKES RESORT
4739 Cumbrian Lakes Dr, KISSIMMEE
5
Beds
5
Baths
2,561 SqFt
Single Family Residence
MLS® # S5125941
FEATURED
Active
$469,950
SUMMERVILLE RESORT
2610 Sunrise Shores Dr, KISSIMMEE
4
Beds
6
Baths
1,804 SqFt
Townhouse
MLS® # S5123862
FEATURED
Active
$449,950
▼ $9,550
CRYSTAL COVE RESORT
932 Emerald Green Ct, KISSIMMEE
4
Beds
3
Baths
1,808 SqFt
Single Family Residence
MLS® # S5124539
FEATURED
Active
$449,000
▲ $4,556
WINDSOR AT WESTSIDE
8912 Sydney Ave, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5115540
FEATURED
Active
$430,000
ENCANTADA
3015 Yellow Lantana Ln, KISSIMMEE
4
Beds
3
Baths
1,636 SqFt
Townhouse
MLS® # S5126724
FEATURED
Active
$429,900
CHAMPIONSGATE, STONEYBROOK
1578 Slice Way, DAVENPORT
4
Beds
3
Baths
1,902 SqFt
Townhouse
MLS® # S5128766
FEATURED
Active
$429,900
CHAMPIONSGATE, STONEYBROOK SOUTH
1566 Plunker Dr, DAVENPORT
4
Beds
3
Baths
1,902 SqFt
Townhouse
MLS® # S5123947
FEATURED
Active
$429,900
CHAMPIONSGATE, STONEYBROOK
1565 Plunker Dr, DAVENPORT
4
Beds
3
Baths
1,902 SqFt
Townhouse
MLS® # S5128755
FEATURED
Active
$424,999
▼ $24,951
MARGARITAVILLE, ROLLING OAKS
3013 Sea Plane Ln, KISSIMMEE
4
Beds
3
Baths
1,410 SqFt
Single Family Residence
MLS® # S5123757
FEATURED
Active
$424,500
▼ $15,450
MARGARITAVILLE, ROLLING OAKS
3037 Sea Plane Ln, KISSIMMEE
2
Beds
3
Baths
1,305 SqFt
Single Family Residence
MLS® # S5112270
FEATURED
Active
$417,000
CHAMPIONSGATE, STONEYBROOK
860 Pebble Beach Dr, DAVENPORT
4
Beds
3
Baths
1,914 SqFt
Townhouse
MLS® # S5124974
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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