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Osceola County Vacation Homes

CountyOrange County | Osceola County | Polk County | Lake County

Osceola County ResortsBella Trae - Bella Vida ResortCaribe Cove Resort - ChampionsGate - Embassy Suites At Sunset Walk - Emerald Island Resort - Encantada - Encore Club at Reunion - Fiesta KeyFormosa ValleyLake BerkleyLucaya Village - Magic Village - Margaritaville Resort Orlando - Melia Orlando Celebration - Paradise PalmsRegal OaksReunion Resort - Solara Resort -  Storey Lake Resort - Summerville Resort - Terra Verde ResortTuscana - Venetian Bay - Veranda Palms - Villas At Seven Dwarfs LaneWindsor Hills ResortWindsor 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.

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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
FEATURED
Active 7665 Fairfax Dr, KISSIMMEE

$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 7639 Wilmington Loop, KISSIMMEE

$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 7527 Marker Ave, KISSIMMEE

$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 561 Lasso Dr, KISSIMMEE

$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 350 Pendant Ct, KISSIMMEE

$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 7740 Sandy Ridge Dr 236, REUNION

$700,000

SPECTRUM AT REUNION, REUNION

7740 Sandy Ridge Dr 236, REUNION

5 Beds 5 Baths 2,630 SqFt Condominium MLS® # S5126016
FEATURED
Active 551 Lasso Dr, KISSIMMEE

$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 8953 Zurich Ln, KISSIMMEE

$675,000

WINDSOR AT WESTSIDE

8953 Zurich Ln, KISSIMMEE

7 Beds 6 Baths 3,314 SqFt Single Family Residence MLS® # S5118295
FEATURED
Active 8571 La Isla Dr, KISSIMMEE

$675,000

EMERALD ISLAND RESORT

8571 La Isla Dr, KISSIMMEE

7 Beds 6 Baths 3,599 SqFt Single Family Residence MLS® # S5126510
FEATURED
Active 7751 Tosteth St, KISSIMMEE

$669,999

WINDSOR HILLS

7751 Tosteth St, KISSIMMEE

6 Beds 4 Baths 2,812 SqFt Single Family Residence MLS® # S5128304
FEATURED
Active 7613 Brookhurst Ln, KISSIMMEE

$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 7541 Marker Ave, KISSIMMEE

$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 331 Pendant Ct, KISSIMMEE

$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 7412 Soiree Way, REUNION

$639,950

▼ $35,050 REUNION

7412 Soiree Way, REUNION

5 Beds 4 Baths 2,764 SqFt Single Family Residence MLS® # S5122099
FEATURED
Active 1800 Tropical Palms Cir, KISSIMMEE

$629,999

▼ $30,001 SOLARA RESORT

1800 Tropical Palms Cir, KISSIMMEE

5 Beds 5 Baths 2,294 SqFt Townhouse MLS® # S5121304
FEATURED
Active 430 Novi Path, KISSIMMEE

$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 341 Lasso Dr, KISSIMMEE

$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 2561 Montego Bay Blvd, KISSIMMEE

$599,999

MONTEGO BAY

2561 Montego Bay Blvd, KISSIMMEE

4 Beds 4 Baths 2,764 SqFt Single Family Residence MLS® # S5128315
FEATURED
Active 661 Drop Shot Dr, DAVENPORT

$599,990

CHAMPIONSGATE, STONEYBROOK

661 Drop Shot Dr, DAVENPORT

5 Beds 5 Baths 3,081 SqFt Single Family Residence MLS® # S5128828
FEATURED
Active 8897 Rhodes St, KISSIMMEE

$598,000

WINDSOR AT WESTSIDE

8897 Rhodes St, KISSIMMEE

6 Beds 5 Baths 3,142 SqFt Single Family Residence MLS® # S5128935
FEATURED
Active 2569 Reading Tr, KISSIMMEE

$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 7719 Comrow St, KISSIMMEE

$549,950

WINDSOR HILLS

7719 Comrow St, KISSIMMEE

4 Beds 4 Baths 1,824 SqFt Single Family Residence MLS® # S5124561
FEATURED
Active 1424 Moon Valley Dr, DAVENPORT

$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 301 Pendant Ct, KISSIMMEE

$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 280 Pendant Ct, KISSIMMEE

$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 8012 Lost Shaker Ln, KISSIMMEE

$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 2685 Oneida Loop, KISSIMMEE

$525,000

INDIAN CREEK

2685 Oneida Loop, KISSIMMEE

5 Beds 4 Baths 2,136 SqFt Single Family Residence MLS® # S5128631
FEATURED
Active 195 Hideaway Beach Ln, KISSIMMEE

$499,999

TERRA VERDE RESORT

195 Hideaway Beach Ln, KISSIMMEE

6 Beds 6 Baths 2,834 SqFt Single Family Residence MLS® # S5129129
FEATURED
Active 8614 La Isla Dr, KISSIMMEE

$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 8886 Geneve Ct, KISSIMMEE

$499,950

WINDSOR AT WESTSIDE

8886 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5119924
FEATURED
Active 3184 Caribbean Soul Dr, KISSIMMEE

$499,000

▼ $96,000 MARGARITAVILLE, ROLLING OAKS

3184 Caribbean Soul Dr, KISSIMMEE

4 Beds 3 Baths 1,712 SqFt Townhouse MLS® # S5103875
FEATURED
Active 4981 Windermere Ave, KISSIMMEE

$489,980

STOREY LAKE RESORT

4981 Windermere Ave, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Townhouse MLS® # S5128849
FEATURED
Active 2993 Sunset Vista Blvd, KISSIMMEE

$489,000

SUNSET LAKES

2993 Sunset Vista Blvd, KISSIMMEE

4 Beds 3 Baths 1,700 SqFt Single Family Residence MLS® # S5123939
FEATURED
Active 2427 Dubai St, KISSIMMEE

$479,950

▼ $10,000 WINDSOR AT WESTSIDE

2427 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Townhouse MLS® # S5123971
FEATURED
Active 8947 Stinger Dr, DAVENPORT

$479,900

CHAMPIONSGATE, STONEYBROOK

8947 Stinger Dr, DAVENPORT

5 Beds 4 Baths 2,072 SqFt Townhouse MLS® # S5128773
FEATURED
Active 4739 Cumbrian Lakes Dr, KISSIMMEE

$474,950

CUMBRIAN LAKES RESORT

4739 Cumbrian Lakes Dr, KISSIMMEE

5 Beds 5 Baths 2,561 SqFt Single Family Residence MLS® # S5125941
FEATURED
Active 2610 Sunrise Shores Dr, KISSIMMEE

$469,950

SUMMERVILLE RESORT

2610 Sunrise Shores Dr, KISSIMMEE

4 Beds 6 Baths 1,804 SqFt Townhouse MLS® # S5123862
FEATURED
Active 932 Emerald Green Ct, KISSIMMEE

$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 8912 Sydney Ave, KISSIMMEE

$449,000

▲ $4,556 WINDSOR AT WESTSIDE

8912 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5115540
FEATURED
Active 3015 Yellow Lantana Ln, KISSIMMEE

$430,000

ENCANTADA

3015 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Townhouse MLS® # S5126724
FEATURED
Active 1578 Slice Way, DAVENPORT

$429,900

CHAMPIONSGATE, STONEYBROOK

1578 Slice Way, DAVENPORT

4 Beds 3 Baths 1,902 SqFt Townhouse MLS® # S5128766
FEATURED
Active 1566 Plunker Dr, DAVENPORT

$429,900

CHAMPIONSGATE, STONEYBROOK SOUTH

1566 Plunker Dr, DAVENPORT

4 Beds 3 Baths 1,902 SqFt Townhouse MLS® # S5123947
FEATURED
Active 1565 Plunker Dr, DAVENPORT

$429,900

CHAMPIONSGATE, STONEYBROOK

1565 Plunker Dr, DAVENPORT

4 Beds 3 Baths 1,902 SqFt Townhouse MLS® # S5128755
FEATURED
Active 3013 Sea Plane Ln, KISSIMMEE

$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 3037 Sea Plane Ln, KISSIMMEE

$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 860 Pebble Beach Dr, DAVENPORT

$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 contact the Donovan Team online 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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