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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.

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FEATURED
Active 915 Golden Bear Dr, REUNION

$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 631 Lasso Dr, KISSIMMEE

$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 7412 Soiree Way, REUNION

$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 601 Lasso Dr, KISSIMMEE

$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 2513 Calla Lily Cv, KISSIMMEE

$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 7802 Indian Ridge Tr S, KISSIMMEE

$449,950

INDIAN RIDGE

7802 Indian Ridge Tr S, KISSIMMEE

4 Beds 2 Baths 1,971 SqFt Single Family Residence MLS® # S5079024
FEATURED
Active 7630 Heritage Crossing Way 301, REUNION

$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 2890 Club Cortile Cir, KISSIMMEE

$299,950

CLUB CORTILE

2890 Club Cortile Cir, KISSIMMEE

4 Beds 3 Baths 1,873 SqFt Townhouse MLS® # S5081352
FEATURED
Active 3202 Sabal Palms Court B, KISSIMMEE

$274,950

GRAND PALMS

3202 Sabal Palms Court B, KISSIMMEE

2 Beds 2 Baths 1,087 SqFt Condominium MLS® # S5081576
FEATURED
Active 3050 Pirates Retreat Ct 101, KISSIMMEE

$254,950

CARIBE COVE

3050 Pirates Retreat Ct 101, KISSIMMEE

2 Beds 2 Baths 1,445 SqFt Condominium MLS® # S5080538
Active 1233 Castle Pines Ct, REUNION

$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 350 Muirfield Loop, REUNION

$9,650,000

REUNION WEST VLGS NORTH

350 Muirfield Loop, REUNION

12 Beds 14 Baths 12,962 SqFt Single Family Residence MLS® # O6064799
Active 510 Muirfield Loop, REUNION

$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 501 Muirfield Loop, REUNION

$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 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 1014 Jack Nicklaus Ct, REUNION

$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 7840 Palmilla Ct, REUNION

$6,450,000

REUNION WEST VLGS NORTH

7840 Palmilla Ct, REUNION

8 Beds 10 Baths 7,928 SqFt Single Family Residence MLS® # O6096699
Active 521 Muirfield Loop, REUNION

$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 222 Pawnee Tr, KISSIMMEE

$5,900,000

HAPPY TRAILS UNIT 04

222 Pawnee Tr, KISSIMMEE

3 Beds 5 Baths 6,559 SqFt Single Family Residence MLS® # P4922879
Active 3140 Friars Cove Rd, SAINT CLOUD

$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 Twilight Tr, KISSIMMEE

$5,500,000

PLEASANT HILL TRAILS UNIT 01

Twilight Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # L4934618
Active 1125 Grand Traverse Pkwy, REUNION

$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 900 Jack Nicklaus Ct, KISSIMMEE

$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 1429 Titian Ct, REUNION

$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 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 5251 Carson St, SAINT CLOUD

$4,699,900

NARCOOSSEE NEW MAP

5251 Carson St, SAINT CLOUD

8 Beds 9 Baths 10,179 SqFt Single Family Residence MLS® # O6059222
Active 4011 South Orange Blossom Tr, KISSIMMEE

$4,200,000

ORANGE BLOSSOM ADD

4011 South Orange Blossom Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6054839
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
Active 804 Desert Mountain Ct, REUNION

$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 2481 Ham Brown Rd, KISSIMMEE

$3,500,000

ACREAGE & UNREC

2481 Ham Brown Rd, KISSIMMEE

3 Beds 2 Baths 2,800 SqFt Single Family Residence MLS® # O6015144
Active 2481 Ham Brown Rd, KISSIMMEE

$3,500,000

ACREAGE & UNREC

2481 Ham Brown Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6015156
Active 2360 Live Oak Lake Rd, SAINT CLOUD

$3,500,000

ACREAGE & UNREC

2360 Live Oak Lake Rd, SAINT CLOUD

0 Beds 0 Baths 0 SqFt Land MLS® # U8151037
Active 2360 Live Oak Lake Rd, SAINT CLOUD

$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 784 Desert Mountain Ct, REUNION

$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 920 Golden Bear Dr, REUNION

$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 236 Acadia Ter, CELEBRATION

$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 1010 Suhls Ln, KISSIMMEE

$3,250,000

ACREAGE & UNREC

1010 Suhls Ln, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6041484
Active N/A, SAINT CLOUD

$3,210,000

▼ $517,500 ACREAGE & UNREC

N/A, SAINT CLOUD

2 Beds 1 Bath 1,390 SqFt Single Family Residence MLS® # O6065656
Active Old Vineland Rd, KISSIMMEE

$3,200,000

NOT PLATTED

Old Vineland Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # R4906147
Active 954 Jack Nicklaus Ct, KISSIMMEE

$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 415 Muirfield Loop, REUNION

$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 906 Jack Nicklaus Ct, KISSIMMEE

$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 713 Eastlawn Dr, CELEBRATION

$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 395 Muirfield Loop, REUNION

$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 6428 Hickory Tree Rd, SAINT CLOUD

$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 4185 Kissimmee Park Rd, SAINT CLOUD

$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 East Irlo Bronson Mem Hwy, KISSIMMEE

$2,700,000

ACREAGE & UNREC

East Irlo Bronson Mem Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5055608
Active Polynesian Isle Blvd, KISSIMMEE

$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.

Browse Osceola County Holiday Home Communities:

  • Town Center Celebration
  • Academy Row
  • Celebration
  • Celebration Area 5
  • East Village Celebration
  • Lake Evalyn
  • Meeting House
  • Roseville Corner
  • Spring Park Terraces At Celebration
  • Terraces At Celebration
  • Terraces At East Village Celebration
  • Water Street Celebration
  • West Village Celebration
  • Artisan Club
  • Carlyle Residences
  • Georgetown
  • Melia Orlando (Formerly Mona Lisa)
  • Mirasol
  • North Village Celebration
  • Siena At Celebration
  • South Village Celebration
  • Champions Club at ChampionsGate
  • Retreat At ChampionsGate
  • Bella Trae
  • ChampionsGate
  • Country Club At ChampionsGate
  • Country Creek
  • The Estates At ChampionsGate
  • Tuscana
  • Birchwood
  • Acadia Estates
  • Bahama Bay II
  • Bass Lake Estates
  • Bay Pointe
  • Bellalago
  • Bellavida
  • Bridgewater
  • Bridgewater At Town Centre
  • Brighton Lakes
  • Buenaventura Lakes
  • Calabria
  • Cane Island
  • Caribe Cove
  • Chatham Park
  • Club Cortile
  • Compass Bay
  • Coral Cay
  • Coopersmith Village
  • Creekside
  • Crescent Lakes
  • Crestwynd Bay
  • Crystal Cove Resort
  • Cumbrian Lakes
  • Cypress Lakes
  • Doral Woods
  • Eagle Pointe
  • Emerald Island Resort
  • Encantada
  • Encore Club at Reunion
  • Fiesta Key
  • Flora Ridge
  • Formosa Gardens
  • Gleneagles At Remington
  • Golden Oak At Walt Disney World
  • Grand Palms
  • Hamiltons Reserve
  • Happy Trails
  • Heritage Key
  • Hidden Forest At Silver Creek
  • Indian Creek
  • Indian Point
  • Indian Ridge
  • Indian Wells
  • Isles Of Bellalago
  • Kissimmee Bay
  • Lake Berkley
  • Legacy Dunes
  • Liberty Village
  • Lindfields
  • Lucaya Village
  • Magic Landings
  • Montego Bay
  • Morgan Point
  • Oak Island Cove
  • Oak Island Harbour
  • Oaks
  • Oakwater
  • Osprey Cove
  • Overoaks
  • Paradise Cay
  • Paradise Cove
  • Paradise Palms
  • Regal Oaks
  • Remington
  • Remington Pointe
  • Rolling Hills
  • Royal Palm Bay
  • Runaway Beach
  • Seasons
  • Somerset
  • Strafford Park
  • Sun Lake
  • Sunset Lakes
  • Sweetwater Club
  • Terra Verde Resort
  • The Hamlets
  • The Villas At Secret Lake
  • Trafalgar Village
  • Tuscany
  • Venetian Bay
  • Veranda Palms
  • Villa Sol
  • Villages At Mango Key Resort
  • Villas At Island Club
  • Villas At Laguna Bay
  • Villas At Secret Lake
  • Villas At Seven Dwarfs Lane
  • Villas At Somerset
  • Whispering Oaks
  • Windsor Hills Resort
  • Windsor Palms Resort
  • Windsor Park
  • Windward Cay
  • Carriage Pointe At Reunion Resort
  • Fairway Ridge North
  • Fairway Ridge South
  • Heritage Preserve
  • Homestead At Reunion Resort
  • Legends Corner
  • Liberty Bluff
  • Masters Landing At Reunion Resort
  • Reunion Grande At Reunion Resort
  • Seven Eagles At Reunion Resort
  • The Estates At Reunion
  • The Terraces At Reunion Resort
  • The Villas At Cabana Court At Reunion
  • The Villas At Sandy Ridge Drive At Reunion Resort
  • The Villas At Sunset View Circle
  • The Villas At Whisper Way At Reunion Resort
  • Villas At Reunion Square
  • Reunion West
  • Kissimmee
  • Patriots Landing
  • Reunion Resort

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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