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Osceola County Vacation Homes

CountyOrange County | Osceola County | Polk County | Lake County

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 3008 Parrot Head Pl, KISSIMMEE

$925,000

▼ $74,999 MARGARITAVILLE RESORT ORLANDO

3008 Parrot Head Pl, KISSIMMEE

3 Beds 4 Baths 1,818 SqFt Single Family Residence MLS® # S5091508
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 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 1522 Corolla Ct, REUNION

$789,949

▼ $1 REUNION, LIBERTY BLUFF

1522 Corolla Ct, REUNION

5 Beds 5 Baths 2,693 SqFt Single Family Residence MLS® # S5099653
FEATURED
Active 8812 Macapa Dr, KISSIMMEE

$729,950

WINDSOR AT WESTSIDE

8812 Macapa Dr, KISSIMMEE

8 Beds 6 Baths 4,041 SqFt Single Family Residence MLS® # S5102453
FEATURED
Active 7613 Wilmington Loop, KISSIMMEE

$729,950

▼ $20,000 ENCORE AT REUNION

7613 Wilmington Loop, KISSIMMEE

6 Beds 6 Baths 2,904 SqFt Single Family Residence MLS® # S5095271
FEATURED
Active 7562 Marker Ave, KISSIMMEE

$714,900

▼ $14,100 ENCORE AT REUNION

7562 Marker Ave, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Single Family Residence MLS® # S5100653
FEATURED
Active 220 Pendant Ct, KISSIMMEE

$699,000

▼ $15,950 ENCORE AT REUNION

220 Pendant Ct, KISSIMMEE

6 Beds 7 Baths 3,317 SqFt Single Family Residence MLS® # S5099537
FEATURED
Active 1469 Rolling Fairway Dr, DAVENPORT

$698,950

▼ $20,000 RETREAT AT CHAMPIONSGATE, CHAMPIONSGATE

1469 Rolling Fairway Dr, DAVENPORT

9 Beds 5 Baths 3,909 SqFt Single Family Residence MLS® # S5100818
FEATURED
Active 2968 Salted Rim Rd, KISSIMMEE

$685,000

▼ $14,950 MARGARITAVILLE, ROLLING OAKS

2968 Salted Rim Rd, KISSIMMEE

3 Beds 4 Baths 1,818 SqFt Single Family Residence MLS® # S5076132
FEATURED
Active 7552 Marker Ave, KISSIMMEE

$669,950

▼ $30,000 ENCORE AT REUNION

7552 Marker Ave, KISSIMMEE

6 Beds 7 Baths 3,317 SqFt Single Family Residence MLS® # S5095251
FEATURED
Active 8415 Secret Key Cv, KISSIMMEE

$599,950

EMERALD ISLAND RESORT

8415 Secret Key Cv, KISSIMMEE

8 Beds 5 Baths 2,914 SqFt Single Family Residence MLS® # S5101311
FEATURED
Active 4243 Paragraph Dr, KISSIMMEE

$555,000

▼ $24,950 STOREY LAKE

4243 Paragraph Dr, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Townhouse MLS® # S5096025
FEATURED
Active 141 Madiera Beach Blvd, KISSIMMEE

$539,950

▼ $35,050 TERRA VERDE

141 Madiera Beach Blvd, KISSIMMEE

4 Beds 4 Baths 2,291 SqFt Single Family Residence MLS® # S5094709
FEATURED
Active 2190 Fleming Mist Pl, KISSIMMEE

$504,990

▼ $9,960 SOLARA RESORT

2190 Fleming Mist Pl, KISSIMMEE

5 Beds 5 Baths 2,283 SqFt Townhouse MLS® # S5085203
FEATURED
Active 8847 Geneve Ct, KISSIMMEE

$480,000

▼ $10,000 WINDSOR AT WESTSIDE

8847 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5097326
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 457 Bogey Dr, DAVENPORT

$399,950

CHAMPIONS POINTE, CHAMPIONS GATE, CHAMPIONSGATE

457 Bogey Dr, DAVENPORT

3 Beds 3 Baths 1,988 SqFt Townhouse MLS® # S5098974
FEATURED
Active 2374 Caravelle Cir, KISSIMMEE

$349,950

CORAL CAY RESORT

2374 Caravelle Cir, KISSIMMEE

5 Beds 3 Baths 1,704 SqFt Townhouse MLS® # S5099612
New FEATURED
Active 2966 Lucayan Harbour Circle 8-105, KISSIMMEE

$349,950

LUCAYA VILLAGE

2966 Lucayan Harbour Circle 8-105, KISSIMMEE

4 Beds 3 Baths 1,694 SqFt Townhouse MLS® # S5103208
FEATURED
Active 856 Assembly Ct, REUNION

$319,950

▼ $18,550 REUNION, CARRIAGE POINTE

856 Assembly Ct, REUNION

3 Beds 3 Baths 1,686 SqFt Townhouse MLS® # S5099913
New 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 2703 Impala Ln, KISSIMMEE

$299,950

▼ $19,050 REGAL OAKS

2703 Impala Ln, KISSIMMEE

4 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5094178
New 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
New 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
New FEATURED
Active 2260 San Vital Dr 106, KISSIMMEE

$275,000

VENETIAN BAY, VENETIAN BAY VILLAGES

2260 San Vital Dr 106, KISSIMMEE

3 Beds 2 Baths 1,296 SqFt Condominium MLS® # S5103160
FEATURED
Active 1301 Tuscan Ter 9104, DAVENPORT

$249,950

TUSCANA

1301 Tuscan Ter 9104, DAVENPORT

3 Beds 2 Baths 1,244 SqFt Condominium MLS® # S5095966
FEATURED
Active 8000 Tuscany Way 4102, DAVENPORT

$224,950

TUSCANA

8000 Tuscany Way 4102, DAVENPORT

2 Beds 2 Baths 1,134 SqFt Condominium MLS® # S5101159
FEATURED
Active 1371 Tuscan Ter 6301, DAVENPORT

$215,000

TUSCANA

1371 Tuscan Ter 6301, DAVENPORT

3 Beds 2 Baths 1,244 SqFt Condominium MLS® # S5100855
FEATURED
Active 8010 Tuscany Way 3103, DAVENPORT

$214,950

TUSCANA

8010 Tuscany Way 3103, DAVENPORT

2 Beds 2 Baths 1,134 SqFt Condominium MLS® # S5101225
FEATURED
Active 1351 Tuscan Ter 8402, DAVENPORT

$195,000

▼ $20,000 TUSCANA

1351 Tuscan Ter 8402, DAVENPORT

2 Beds 2 Baths 1,134 SqFt Condominium MLS® # S5088600
Active 4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

$7,899,500

▼ $400 ACREAGE & UNREC

4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6158900
Active 350 Muirfield Loop, REUNION

$7,750,000

▼ $675,000 REUNION WEST VLGS NORTH

350 Muirfield Loop, REUNION

12 Beds 14 Baths 12,962 SqFt Single Family Residence MLS® # S5091482
Active 510 Muirfield Loop, REUNION

$7,495,000

▼ $255,000 REUNION WEST VLGS NORTH

510 Muirfield Loop, REUNION

12 Beds 16 Baths 15,319 SqFt Single Family Residence MLS® # O6140468
Active 3724 Hickory Tree Rd, SAINT CLOUD

$7,000,000

ST CLOUD MANOR ESTATES 02

3724 Hickory Tree Rd, SAINT CLOUD

0 Beds 0 Baths 0 SqFt Land MLS® # S5058614
Active East Irlo Bronson Mem Hwy, SAINT CLOUD

$6,800,000

▼ $800,000 ACREAGE & UNREC

East Irlo Bronson Mem Hwy, SAINT CLOUD

0 Beds 0 Baths 0 SqFt Land MLS® # S5043922
Active 925 Desert Mountain Ct, REUNION

$6,550,000

▼ $185,000 REUNION WEST VILLAGE 3A

925 Desert Mountain Ct, REUNION

12 Beds 17 Baths 12,602 SqFt Single Family Residence MLS® # L4943214
New
Active Simpson Rd, KISSIMMEE

$6,250,000

Simpson Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5103046
Active 5710 Nova Rd, SAINT CLOUD

$5,640,000

▼ $1,360,000 ACREAGE & UNREC

5710 Nova Rd, SAINT CLOUD

0 Beds 0 Baths 0 SqFt Land MLS® # O6027030
Active 7650 Holopaw Groves Rd, SAINT CLOUD

$5,635,000

7650 Holopaw Groves Rd, SAINT CLOUD

0 Beds 0 Baths 0 SqFt Land MLS® # T3509774
Active Twilight Tr, KISSIMMEE

$5,500,000

PLEASANT HILL TRAILS UNIT 01

Twilight Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # L4943863
Active 900 Golden Bear Dr, REUNION

$5,500,000

▼ $1,000,000 REUNION WEST VILLAGE 03A

900 Golden Bear Dr, REUNION

10 Beds 13 Baths 9,735 SqFt Single Family Residence MLS® # O6168288
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 1121 Grand Traverse Pkwy, REUNION

$4,799,000

▼ $151,000 REUNION WEST VILLAGE 03A

1121 Grand Traverse Pkwy, REUNION

9 Beds 12 Baths 10,541 SqFt Single Family Residence MLS® # O6141474
Active 804 Desert Mountain Ct, REUNION

$4,450,000

▼ $50,000 REUNION WEST VILLAGE 3A

804 Desert Mountain Ct, REUNION

10 Beds 12 Baths 8,676 SqFt Single Family Residence MLS® # O6189131
Active 2650 Missouri Ave, SAINT CLOUD

$4,000,000

SEMINOLE LAND & INV CO

2650 Missouri Ave, SAINT CLOUD

0 Beds 0 Baths 0 SqFt Land MLS® # O6096052

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.


Communities in Osceola County


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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