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
$1,090,000
ENCORE AT REUNION, REUNION RESORT
7639 Wilmington Loop, KISSIMMEE
11
Beds
10
Baths
4,707 SqFt
Single Family Residence
MLS® # S5116680
FEATURED
Active
$717,950
▼ $2,000
ENCORE AT REUNION, REUNION RESORT
451 Lasso Dr, KISSIMMEE
8
Beds
7
Baths
3,401 SqFt
Single Family Residence
MLS® # S5113342
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
$663,000
▼ $2,000
ENCORE AT REUNION, REUNION RESORT
7617 Brookhurst Ln, KISSIMMEE
8
Beds
7
Baths
3,412 SqFt
Single Family Residence
MLS® # S5113348
FEATURED
Active
$648,950
CHAMPIONSGATE, STONEYBROOK
9022 Stinger Dr, DAVENPORT
6
Beds
6
Baths
3,339 SqFt
Single Family Residence
MLS® # S5115988
New
FEATURED
Active
$625,000
WINDSOR AT WESTSIDE
8939 Zurich Ln, KISSIMMEE
7
Beds
7
Baths
3,314 SqFt
Single Family Residence
MLS® # S5119643
FEATURED
Active
$599,999
▼ $28,951
ENCORE AT REUNION, REUNION RESORT
368 Southfield St, KISSIMMEE
4
Beds
3
Baths
2,363 SqFt
Single Family Residence
MLS® # S5114625
FEATURED
Active
$599,950
▼ $9,550
WINDSOR HILLS
2619 Archfeld Blvd, KISSIMMEE
5
Beds
5
Baths
2,297 SqFt
Single Family Residence
MLS® # S5114610
FEATURED
Active
$574,950
▼ $25,000
MARGARITAVILLE, ROLLING OAKS
2918 Salted Rim Rd, KISSIMMEE
4
Beds
3
Baths
1,410 SqFt
Single Family Residence
MLS® # S5106497
FEATURED
Active
$549,999
▼ $18,951
MARGARITAVILLE, ROLLING OAKS
2968 Salted Rim Rd, KISSIMMEE
3
Beds
4
Baths
1,818 SqFt
Single Family Residence
MLS® # S5076132
FEATURED
Active
$549,950
▼ $29,000
ENCORE AT REUNION, REUNION RESORT
280 Pendant Ct, KISSIMMEE
5
Beds
5
Baths
2,570 SqFt
Single Family Residence
MLS® # S5112064
FEATURED
Active
$519,950
STOREY LAKE, COVE AT STOREY LAKE
4297 Paragraph Dr, KISSIMMEE
4
Beds
3
Baths
1,914 SqFt
Townhouse
MLS® # S5116872
FEATURED
Active
$515,515
EMERALD ISLAND RESORT
8614 La Isla Dr, KISSIMMEE
5
Beds
4
Baths
2,317 SqFt
Single Family Residence
MLS® # S5119558
New
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
$474,900
STOREY LAKE
4927 Windermere Ave, KISSIMMEE
4
Beds
3
Baths
1,914 SqFt
Townhouse
MLS® # S5116075
FEATURED
Active
$460,000
CUMBRIAN LAKES
1201 Winding Willow Ct, KISSIMMEE
4
Beds
3
Baths
1,829 SqFt
Single Family Residence
MLS® # S5118183
FEATURED
Active
$449,950
EMERALD ISLAND RESORT
8457 Secret Key Cv, KISSIMMEE
4
Beds
3
Baths
1,542 SqFt
Single Family Residence
MLS® # S5114617
FEATURED
Active
$444,444
▼ $25,506
WINDSOR AT WESTSIDE
8912 Sydney Ave, KISSIMMEE
5
Beds
5
Baths
2,263 SqFt
Townhouse
MLS® # S5115540
FEATURED
Active
$439,950
MAGIC VILLAGE
3169 Pantanal Ln, KISSIMMEE
3
Beds
4
Baths
2,181 SqFt
Townhouse
MLS® # S5114284
FEATURED
Active
$435,000
ROLLING HILLS, ROLLING HILLS ESTATES
7959 Magnolia Bend Ct, KISSIMMEE
4
Beds
3
Baths
1,975 SqFt
Single Family Residence
MLS® # S5111630
FEATURED
Active
$429,000
▼ $10,000
MARGARITAVILLE, ROLLING OAKS
3075 Key Lime Loop, KISSIMMEE
2
Beds
3
Baths
1,305 SqFt
Single Family Residence
MLS® # S5115878
FEATURED
Active
$424,950
▼ $25,000
REUNION FAIRWAYS, REUNION
7920 Draw St, REUNION
3
Beds
3
Baths
1,704 SqFt
Townhouse
MLS® # S5103314
FEATURED
Active
$424,900
▼ $75,050
MARGARITAVILLE, ROLLING OAKS
3044 Salted Rim Rd, KISSIMMEE
2
Beds
3
Baths
1,305 SqFt
Single Family Residence
MLS® # S5105327
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
New
FEATURED
Active
$399,950
INDIAN RIDGE OAKS
7833 Turkey Oak Ln, KISSIMMEE
4
Beds
2
Baths
1,601 SqFt
Single Family Residence
MLS® # S5119887
New
FEATURED
Active
$395,000
MARGARITAVILLE, ROLLING OAKS
3065 Caribbean Soul Dr, KISSIMMEE
3
Beds
3
Baths
1,394 SqFt
Townhouse
MLS® # S5119645
FEATURED
Active
$380,000
ENCANTADA
3083 Yellow Lantana Ln, KISSIMMEE
4
Beds
3
Baths
1,340 SqFt
Townhouse
MLS® # S5116892
FEATURED
Active
$379,950
MARGARITAVILLE, ROLLING OAKS
8178 Coconut Pl, KISSIMMEE
3
Beds
3
Baths
1,550 SqFt
Townhouse
MLS® # S5118698
FEATURED
Active
$375,000
MORGAN POINT
2302 Aberdeen Ct, KISSIMMEE
3
Beds
2
Baths
1,486 SqFt
Single Family Residence
MLS® # S5119420
FEATURED
Active
$359,950
▼ $20,000
MARGARITAVILLE, ROLLING OAKS
2980 On The Rocks Pt, KISSIMMEE
2
Beds
3
Baths
1,394 SqFt
Townhouse
MLS® # S5112676
FEATURED
Active
$350,000
REGAL OAKS
2621 Bugatti Ct, KISSIMMEE
3
Beds
3
Baths
1,474 SqFt
Townhouse
MLS® # S5118292
FEATURED
Active
$349,950
REGAL OAKS
2618 Bugatti Ct, KISSIMMEE
2
Beds
3
Baths
1,350 SqFt
Townhouse
MLS® # S5116340
FEATURED
Active
$328,950
▼ $16,050
WINDSOR HILLS, VENTURA AT WINDSOR HILLS
2778 Almaton Loop 401, KISSIMMEE
3
Beds
2
Baths
1,246 SqFt
Condominium
MLS® # S5110893
FEATURED
Active
$325,000
▼ $24,950
ENCANTADA
3189 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5108427
FEATURED
Active
$320,000
▼ $29,950
CORAL CAY RESORT
2374 Caravelle Cir, KISSIMMEE
5
Beds
3
Baths
1,704 SqFt
Townhouse
MLS® # S5099612
FEATURED
Active
$319,900
▼ $19,600
ENCANTADA
3145 Yellow Lantana Ln, KISSIMMEE
3
Beds
3
Baths
1,295 SqFt
Townhouse
MLS® # S5117216
FEATURED
Active
$310,000
VENETIAN BAY
2200 San Zanobi Dr 108, KISSIMMEE
4
Beds
3
Baths
1,470 SqFt
Condominium
MLS® # S5102991
FEATURED
Active
$299,950
WINDSOR HILLS, VENTURA AT WINDSOR HILLS
7671 Comrow St 202, KISSIMMEE
2
Beds
2
Baths
1,081 SqFt
Condominium
MLS® # S5111171
FEATURED
Active
$289,900
PARADISE CAY
5213 Paradise Cay Cir, KISSIMMEE
3
Beds
3
Baths
1,187 SqFt
Townhouse
MLS® # S5115552
New
FEATURED
Active
$259,950
SWEETWATER CLUB
2452 Sweetwater Club Cir 27, KISSIMMEE
3
Beds
2
Baths
1,220 SqFt
Condominium
MLS® # S5119469
FEATURED
Active
$224,950
ROYAL PALM BAY
2022 Royal Bay Blvd 94, KISSIMMEE
3
Beds
2
Baths
1,326 SqFt
Condominium
MLS® # S5116475
FEATURED
Active
$219,000
▼ $19,700
TUSCANA
1301 Tuscan Ter 9104, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condominium
MLS® # S5095966
FEATURED
Active
$215,000
CARIBE COVE
9051 Treasure Trove Ln 307, KISSIMMEE
2
Beds
2
Baths
1,445 SqFt
Condominium
MLS® # S5115202
FEATURED
Active
$209,950
▼ $5,000
TUSCANA
8010 Tuscany Way 3103, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5101225
FEATURED
Active
$209,950
TUSCANA RESORT
1301 Tuscan Ter 9403, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5112529
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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