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
$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
$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
$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
$729,950
WINDSOR AT WESTSIDE
8812 Macapa Dr, KISSIMMEE
8
Beds
6
Baths
4,041 SqFt
Single Family Residence
MLS® # S5102453
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
$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
$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
$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
$648,950
▼ $21,000
ENCORE AT REUNION
7552 Marker Ave, KISSIMMEE
6
Beds
7
Baths
3,317 SqFt
Single Family Residence
MLS® # S5095251
FEATURED
Active
$599,950
EMERALD ISLAND RESORT
8415 Secret Key Cv, KISSIMMEE
8
Beds
5
Baths
2,914 SqFt
Single Family Residence
MLS® # S5101311
FEATURED
Active
$595,000
MARGARITAVILLE, ROLLING OAKS
3184 Caribbean Soul Dr, KISSIMMEE
4
Beds
3
Baths
1,712 SqFt
Townhouse
MLS® # S5103875
FEATURED
Active
$574,950
▼ $15,000
ACADIA ESTATES, WYNDHAM POINTE
8035 Acadia Estates Ct, KISSIMMEE
6
Beds
5
Baths
2,769 SqFt
Single Family Residence
MLS® # S5098360
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
$499,950
▼ $40,000
TERRA VERDE
141 Madiera Beach Blvd, KISSIMMEE
4
Beds
4
Baths
2,291 SqFt
Single Family Residence
MLS® # S5094709
FEATURED
Active
$474,950
▼ $5,050
WINDSOR AT WESTSIDE
8847 Geneve Ct, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5097326
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
$399,950
CHAMPIONS POINTE, CHAMPIONS GATE, CHAMPIONSGATE
457 Bogey Dr, DAVENPORT
3
Beds
3
Baths
1,988 SqFt
Townhouse
MLS® # S5098974
FEATURED
Active
$349,950
CORAL CAY RESORT
2374 Caravelle Cir, KISSIMMEE
5
Beds
3
Baths
1,704 SqFt
Townhouse
MLS® # S5099612
FEATURED
Active
$349,950
LUCAYA VILLAGE
2966 Lucayan Harbour Circle 8-105, KISSIMMEE
4
Beds
3
Baths
1,694 SqFt
Townhouse
MLS® # S5103208
FEATURED
Active
$319,950
CLUB CORTILE
2837 Club Cortile Cir, KISSIMMEE
4
Beds
3
Baths
1,873 SqFt
Townhouse
MLS® # S5103357
FEATURED
Active
$310,000
▼ $9,950
REUNION, CARRIAGE POINTE
856 Assembly Ct, REUNION
3
Beds
3
Baths
1,686 SqFt
Townhouse
MLS® # S5099913
FEATURED
Active
$310,000
VENETIAN BAY
2200 San Zanobi Dr 108, KISSIMMEE
4
Beds
3
Baths
1,470 SqFt
Condominium
MLS® # S5102991
FEATURED
Active
$289,000
ENCANTADA
3018 Red Ginger Rd, KISSIMMEE
2
Beds
3
Baths
1,161 SqFt
Townhouse
MLS® # S5103647
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
$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
$249,950
TUSCANA
1301 Tuscan Ter 9104, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condominium
MLS® # S5095966
FEATURED
Active
$215,000
TUSCANA
1371 Tuscan Ter 6301, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condominium
MLS® # S5100855
FEATURED
Active
$214,950
TUSCANA
8010 Tuscany Way 3103, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5101225
FEATURED
Active
$209,950
▼ $15,000
TUSCANA
8000 Tuscany Way 4102, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5101159
FEATURED
Active
$195,000
▼ $20,000
TUSCANA
1351 Tuscan Ter 8402, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5088600
Active
$7,899,250
▼ $250
ACREAGE & UNREC
4708 West Irlo Bronson Memorial Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6158900
Active
$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
$7,000,000
▲ $4,800,000
SEMINOLE LAND & INV CO
Friars Cove Rd, SAINT CLOUD
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6089960
Active
$7,000,000
ST CLOUD MANOR ESTATES 02
3724 Hickory Tree Rd, SAINT CLOUD
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5058614
Active
$6,498,700
▼ $51,300
REUNION WEST VILLAGE 3A
925 Desert Mountain Ct, REUNION
12
Beds
17
Baths
12,602 SqFt
Single Family Residence
MLS® # L4943214
Active
$6,250,000
Simpson Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5103046
Active
$5,640,000
▼ $1,360,000
ACREAGE & UNREC
5710 Nova Rd, SAINT CLOUD
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6027030
Active
$5,635,000
7650 Holopaw Groves Rd, SAINT CLOUD
0
Beds
0
Baths
0 SqFt
Land
MLS® # T3509774
Active
$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
$4,885,000
▼ $615,000
PLEASANT HILL TRAILS UNIT 01
Twilight Tr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # L4943863
Active
$4,800,000
FLA FRUIT & TRUCKLAND CO
South Goodman Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # R4905868
Active
$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
$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.
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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