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Osceola County Vacation Homes
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
$1,299,950
REUNION, MASTERS LANDING, REUNION WEST VLGS NORTH
915 Golden Bear Dr, REUNION
5
Beds
6
Baths
3,406 SqFt
Single Family Residence
MLS® # S5080135
FEATURED
Active
$985,000
▼ $65,000
ENCORE AT REUNION, REUNION WEST
631 Lasso Dr, KISSIMMEE
10
Beds
10
Baths
4,724 SqFt
Single Family Residence
MLS® # S5072544
FEATURED
Active
$775,000
▼ $74,950
REUNION RESORT, HOMESTEAD
7412 Soiree Way, REUNION
5
Beds
4
Baths
2,764 SqFt
Single Family Residence
MLS® # S5074775
FEATURED
Active
$749,950
▼ $30,000
ENCORE AT REUNION, REUNION WEST
601 Lasso Dr, KISSIMMEE
6
Beds
7
Baths
3,099 SqFt
Single Family Residence
MLS® # S5079651
FEATURED
Active
$534,950
CRESCENT LAKES, CALLA LILY COVE
2513 Calla Lily Cv, KISSIMMEE
7
Beds
3
Baths
2,679 SqFt
Single Family Residence
MLS® # S5076964
FEATURED
Active
$449,950
INDIAN RIDGE
7802 Indian Ridge Tr S, KISSIMMEE
4
Beds
2
Baths
1,971 SqFt
Single Family Residence
MLS® # S5079024
FEATURED
Active
$299,950
▼ $15,000
HERITAGE CROSSING, REUNION
7630 Heritage Crossing Way 301, REUNION
3
Beds
2
Baths
1,344 SqFt
Condominium
MLS® # S5076980
FEATURED
Active
$299,950
CLUB CORTILE
2890 Club Cortile Cir, KISSIMMEE
4
Beds
3
Baths
1,873 SqFt
Townhouse
MLS® # S5081352
FEATURED
Active
$274,950
GRAND PALMS
3202 Sabal Palms Court B, KISSIMMEE
2
Beds
2
Baths
1,087 SqFt
Condominium
MLS® # S5081576
FEATURED
Active
$254,950
CARIBE COVE
3050 Pirates Retreat Ct 101, KISSIMMEE
2
Beds
2
Baths
1,445 SqFt
Condominium
MLS® # S5080538
Active
$9,999,000
REUNION WEST VILLAGE 03A
1233 Castle Pines Ct, REUNION
10
Beds
14
Baths
11,027 SqFt
Single Family Residence
MLS® # O6064800
Active
$9,650,000
REUNION WEST VLGS NORTH
350 Muirfield Loop, REUNION
12
Beds
14
Baths
12,962 SqFt
Single Family Residence
MLS® # O6064799
Active
$9,250,000
▲ $300,000
REUNION WEST VLGS NORTH
510 Muirfield Loop, REUNION
12
Beds
16
Baths
15,319 SqFt
Single Family Residence
MLS® # O6004601
Active
$7,499,000
▼ $1,000
REUNION WEST VLGS NORTH
501 Muirfield Loop, REUNION
9
Beds
12
Baths
10,637 SqFt
Single Family Residence
MLS® # O6092393
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
$6,900,000
▼ $599,000
REUNION WEST FAIRWAYS 17 & 18
1014 Jack Nicklaus Ct, REUNION
10
Beds
12
Baths
9,020 SqFt
Single Family Residence
MLS® # S5061902
New
Active
$6,450,000
REUNION WEST VLGS NORTH
7840 Palmilla Ct, REUNION
8
Beds
10
Baths
7,928 SqFt
Single Family Residence
MLS® # O6096699
Active
$5,995,000
▼ $255,000
REUNION WEST VLGS NORTH
521 Muirfield Loop, REUNION
12
Beds
15
Baths
11,248 SqFt
Single Family Residence
MLS® # O6008200
Active
$5,900,000
HAPPY TRAILS UNIT 04
222 Pawnee Tr, KISSIMMEE
3
Beds
5
Baths
6,559 SqFt
Single Family Residence
MLS® # P4922879
Active
$5,757,000
▼ $242,999
ACREAGE & UNREC
3140 Friars Cove Rd, SAINT CLOUD
6
Beds
5
Baths
4,890 SqFt
Single Family Residence
MLS® # O6095385
Active
$5,500,000
PLEASANT HILL TRAILS UNIT 01
Twilight Tr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # L4934618
Active
$5,275,000
▼ $23,000
REUNION WEST VILLAGE 03A
1125 Grand Traverse Pkwy, REUNION
11
Beds
14
Baths
11,027 SqFt
Single Family Residence
MLS® # O6076795
Active
$5,150,000
▼ $540,000
REUNION WEST FAIRWAYS 17 & 18
900 Jack Nicklaus Ct, KISSIMMEE
8
Beds
12
Baths
9,558 SqFt
Single Family Residence
MLS® # O6018108
Active
$4,999,000
REUNION PH 02 PRCL 01 & 1A
1429 Titian Ct, REUNION
8
Beds
12
Baths
9,171 SqFt
Single Family Residence
MLS® # O6080268
Active
$4,800,000
FLA FRUIT & TRUCKLAND CO
South Goodman Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # R4905868
Active
$4,699,900
NARCOOSSEE NEW MAP
5251 Carson St, SAINT CLOUD
8
Beds
9
Baths
10,179 SqFt
Single Family Residence
MLS® # O6059222
Active
$4,200,000
ORANGE BLOSSOM ADD
4011 South Orange Blossom Tr, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6054839
Active
$4,000,000
SEMINOLE LAND & INV CO
2650 Missouri Ave, SAINT CLOUD
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6096052
Active
$4,000,000
REUNION WEST VILLAGE 03A
804 Desert Mountain Ct, REUNION
10
Beds
12
Baths
8,676 SqFt
Single Family Residence
MLS® # O6089048
Active
$3,500,000
ACREAGE & UNREC
2481 Ham Brown Rd, KISSIMMEE
3
Beds
2
Baths
2,800 SqFt
Single Family Residence
MLS® # O6015144
Active
$3,500,000
ACREAGE & UNREC
2481 Ham Brown Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6015156
Active
$3,500,000
ACREAGE & UNREC
2360 Live Oak Lake Rd, SAINT CLOUD
0
Beds
0
Baths
0 SqFt
Land
MLS® # U8151037
Active
$3,500,000
ACREAGE & UNREC
2360 Live Oak Lake Rd, SAINT CLOUD
4
Beds
3
Baths
2,760 SqFt
Single Family Residence
MLS® # U8151018
Active
$3,400,000
REUNION WEST VILLAGE 03A
784 Desert Mountain Ct, REUNION
13
Beds
13
Baths
6,333 SqFt
Single Family Residence
MLS® # O6072598
Active
$3,350,000
REUNION WEST VLGS NORTH
920 Golden Bear Dr, REUNION
8
Beds
10
Baths
5,628 SqFt
Single Family Residence
MLS® # O6074933
Active
$3,275,000
CELEBRATION NORTH VILLAGE UNIT 02
236 Acadia Ter, CELEBRATION
6
Beds
5
Baths
6,700 SqFt
Single Family Residence
MLS® # O6031097
Active
$3,250,000
ACREAGE & UNREC
1010 Suhls Ln, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6041484
Active
$3,210,000
▼ $517,500
ACREAGE & UNREC
N/A, SAINT CLOUD
2
Beds
1
Bath
1,390 SqFt
Single Family Residence
MLS® # O6065656
Active
$3,200,000
NOT PLATTED
Old Vineland Rd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # R4906147
Active
$3,190,000
REUNION WEST FAIRWAYS 17 18
954 Jack Nicklaus Ct, KISSIMMEE
8
Beds
10
Baths
5,896 SqFt
Single Family Residence
MLS® # O6090732
Active
$3,099,000
▼ $276,000
REUNION WEST VLGS NORTH
415 Muirfield Loop, REUNION
8
Beds
11
Baths
7,360 SqFt
Single Family Residence
MLS® # O6085905
Active
$2,965,000
▼ $235,000
REUNION WEST
906 Jack Nicklaus Ct, KISSIMMEE
8
Beds
10
Baths
5,590 SqFt
Single Family Residence
MLS® # O6066876
Active
$2,950,000
CELEBRATION EAST VILLAGE UN 1
713 Eastlawn Dr, CELEBRATION
6
Beds
6
Baths
5,941 SqFt
Single Family Residence
MLS® # O6088045
Active
$2,900,000
▼ $100,000
REUNION WEST VLGS NORTH
395 Muirfield Loop, REUNION
5
Beds
7
Baths
5,563 SqFt
Single Family Residence
MLS® # O6080845
Active
$2,900,000
SEMINOLE LAND & INV CO
6428 Hickory Tree Rd, SAINT CLOUD
6
Beds
4
Baths
3,010 SqFt
Single Family Residence
MLS® # S5076060
Active
$2,795,000
▼ $65,000
OSCEOLA GROVES
4185 Kissimmee Park Rd, SAINT CLOUD
4
Beds
5
Baths
6,932 SqFt
Single Family Residence
MLS® # O6032078
Active
$2,700,000
ACREAGE & UNREC
East Irlo Bronson Mem Hwy, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # S5055608
Active
$2,700,000
▲ $500,000
CALYPSO CAY COMM PH 02
Polynesian Isle Blvd, KISSIMMEE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5942296
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.