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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 7639 Wilmington Loop, KISSIMMEE

$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 451 Lasso Dr, KISSIMMEE

$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 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 7617 Brookhurst Ln, KISSIMMEE

$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 9022 Stinger Dr, DAVENPORT

$648,950

CHAMPIONSGATE, STONEYBROOK

9022 Stinger Dr, DAVENPORT

6 Beds 6 Baths 3,339 SqFt Single Family Residence MLS® # S5115988
New FEATURED
Active 8939 Zurich Ln, KISSIMMEE

$625,000

WINDSOR AT WESTSIDE

8939 Zurich Ln, KISSIMMEE

7 Beds 7 Baths 3,314 SqFt Single Family Residence MLS® # S5119643
FEATURED
Active 368 Southfield St, KISSIMMEE

$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 2619 Archfeld Blvd, KISSIMMEE

$599,950

▼ $9,550 WINDSOR HILLS

2619 Archfeld Blvd, KISSIMMEE

5 Beds 5 Baths 2,297 SqFt Single Family Residence MLS® # S5114610
FEATURED
Active 2918 Salted Rim Rd, KISSIMMEE

$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 2968 Salted Rim Rd, KISSIMMEE

$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 280 Pendant Ct, KISSIMMEE

$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 4297 Paragraph Dr, KISSIMMEE

$519,950

STOREY LAKE, COVE AT STOREY LAKE

4297 Paragraph Dr, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Townhouse MLS® # S5116872
FEATURED
Active 8614 La Isla Dr, KISSIMMEE

$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 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 4927 Windermere Ave, KISSIMMEE

$474,900

STOREY LAKE

4927 Windermere Ave, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Townhouse MLS® # S5116075
FEATURED
Active 1201 Winding Willow Ct, KISSIMMEE

$460,000

CUMBRIAN LAKES

1201 Winding Willow Ct, KISSIMMEE

4 Beds 3 Baths 1,829 SqFt Single Family Residence MLS® # S5118183
FEATURED
Active 8457 Secret Key Cv, KISSIMMEE

$449,950

EMERALD ISLAND RESORT

8457 Secret Key Cv, KISSIMMEE

4 Beds 3 Baths 1,542 SqFt Single Family Residence MLS® # S5114617
FEATURED
Active 8912 Sydney Ave, KISSIMMEE

$444,444

▼ $25,506 WINDSOR AT WESTSIDE

8912 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Townhouse MLS® # S5115540
FEATURED
Active 3169 Pantanal Ln, KISSIMMEE

$439,950

MAGIC VILLAGE

3169 Pantanal Ln, KISSIMMEE

3 Beds 4 Baths 2,181 SqFt Townhouse MLS® # S5114284
FEATURED
Active 7959 Magnolia Bend Ct, KISSIMMEE

$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 3075 Key Lime Loop, KISSIMMEE

$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 7920 Draw St, REUNION

$424,950

▼ $25,000 REUNION FAIRWAYS, REUNION

7920 Draw St, REUNION

3 Beds 3 Baths 1,704 SqFt Townhouse MLS® # S5103314
FEATURED
Active 3044 Salted Rim Rd, KISSIMMEE

$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 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
New FEATURED
Active 7833 Turkey Oak Ln, KISSIMMEE

$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 3065 Caribbean Soul Dr, KISSIMMEE

$395,000

MARGARITAVILLE, ROLLING OAKS

3065 Caribbean Soul Dr, KISSIMMEE

3 Beds 3 Baths 1,394 SqFt Townhouse MLS® # S5119645
FEATURED
Active 3083 Yellow Lantana Ln, KISSIMMEE

$380,000

ENCANTADA

3083 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,340 SqFt Townhouse MLS® # S5116892
FEATURED
Active 8178 Coconut Pl, KISSIMMEE

$379,950

MARGARITAVILLE, ROLLING OAKS

8178 Coconut Pl, KISSIMMEE

3 Beds 3 Baths 1,550 SqFt Townhouse MLS® # S5118698
FEATURED
Active 2302 Aberdeen Ct, KISSIMMEE

$375,000

MORGAN POINT

2302 Aberdeen Ct, KISSIMMEE

3 Beds 2 Baths 1,486 SqFt Single Family Residence MLS® # S5119420
FEATURED
Active 2980 On The Rocks Pt, KISSIMMEE

$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 2621 Bugatti Ct, KISSIMMEE

$350,000

REGAL OAKS

2621 Bugatti Ct, KISSIMMEE

3 Beds 3 Baths 1,474 SqFt Townhouse MLS® # S5118292
FEATURED
Active 2618 Bugatti Ct, KISSIMMEE

$349,950

REGAL OAKS

2618 Bugatti Ct, KISSIMMEE

2 Beds 3 Baths 1,350 SqFt Townhouse MLS® # S5116340
FEATURED
Active 2778 Almaton Loop 401, KISSIMMEE

$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 3189 Yellow Lantana Ln, KISSIMMEE

$325,000

▼ $24,950 ENCANTADA

3189 Yellow Lantana Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5108427
FEATURED
Active 2374 Caravelle Cir, KISSIMMEE

$320,000

▼ $29,950 CORAL CAY RESORT

2374 Caravelle Cir, KISSIMMEE

5 Beds 3 Baths 1,704 SqFt Townhouse MLS® # S5099612
FEATURED
Active 3145 Yellow Lantana Ln, KISSIMMEE

$319,900

▼ $19,600 ENCANTADA

3145 Yellow Lantana Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Townhouse MLS® # S5117216
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 7671 Comrow St 202, KISSIMMEE

$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 5213 Paradise Cay Cir, KISSIMMEE

$289,900

PARADISE CAY

5213 Paradise Cay Cir, KISSIMMEE

3 Beds 3 Baths 1,187 SqFt Townhouse MLS® # S5115552
New FEATURED
Active 2452 Sweetwater Club Cir 27, KISSIMMEE

$259,950

SWEETWATER CLUB

2452 Sweetwater Club Cir 27, KISSIMMEE

3 Beds 2 Baths 1,220 SqFt Condominium MLS® # S5119469
FEATURED
Active 2022 Royal Bay Blvd 94, KISSIMMEE

$224,950

ROYAL PALM BAY

2022 Royal Bay Blvd 94, KISSIMMEE

3 Beds 2 Baths 1,326 SqFt Condominium MLS® # S5116475
FEATURED
Active 1301 Tuscan Ter 9104, DAVENPORT

$219,000

▼ $19,700 TUSCANA

1301 Tuscan Ter 9104, DAVENPORT

3 Beds 2 Baths 1,244 SqFt Condominium MLS® # S5095966
FEATURED
Active 9051 Treasure Trove Ln 307, KISSIMMEE

$215,000

CARIBE COVE

9051 Treasure Trove Ln 307, KISSIMMEE

2 Beds 2 Baths 1,445 SqFt Condominium MLS® # S5115202
FEATURED
Active 8010 Tuscany Way 3103, DAVENPORT

$209,950

▼ $5,000 TUSCANA

8010 Tuscany Way 3103, DAVENPORT

2 Beds 2 Baths 1,134 SqFt Condominium MLS® # S5101225
FEATURED
Active 1301 Tuscan Ter 9403, DAVENPORT

$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 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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