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

1148 GRAND TRAVERSE PKWY,

1148 Grand Traverse Pkwy, Reunion

1519176942
Check out this once-in-a-lifetime opportunity to experience superior excellence …more
$11,500,000
835 GOLDEN BEAR DR,

835 Golden Bear Dr, Reunion

1013102852
The Reunion Castle offers all the amenities of a 5-star resort. This property wa …more
$6,125,000
3140 FRIARS COVE RD,

3140 Friars Cove Rd, Saint Cloud

6548902
Pass through the gated entrance of this lakefront estate and experience one of S …more
$5,999,999
501 MUIRFIELD LOOP,

501 Muirfield Loop, Reunion

913106302
This home was recently completed by award winning Custom home builder McNally Co …more
$5,900,000
7844 PALMILLA CT,

7844 Palmilla Ct, Reunion

81185262
This Stunning custom 8 bed, 10 bath home is a magnificent masterpiece of modern …more
$5,600,000
736 DESERT MOUNTAIN CT,

736 Desert Mountain Ct, Reunion

131693012
This incredible mansion is located in the prestigious Reunion Resort and has 13 …more
$5,350,000
8005 TWIN EAGLES LOOP,

8005 Twin Eagles Loop, Reunion

1419124422
This amazing one-of-a-kind luxurious property with 14 themed bedroom suites, 14 …more
$4,317,500
1125 GRAND TRAVERSE PKWY,

1125 Grand Traverse Pkwy, Reunion

1114103772
Beautiful Estate Home in Reunion Resort! Currently used as a vacation rental wit …more
$4,250,000
8168 VALHALLA TER,

8168 Valhalla Ter, Reunion

1012125002
Luxurious contemporary fully furnished newly built custom home in prestigious Re …more
$4,000,000
5000 E IRLO BRONSON MEMORIAL HWY,

5000 E Irlo Bronson Memorial Hwy, Saint Cloud

5438962
Executive 5 acre private residence. Relax and enjoy the unrestricted views (both …more
$3,900,000
918 JACK NICKLAUS CT,

918 Jack Nicklaus Ct, Kissimmee

6882992
A palatial 2-storey home located in Bears Den, a Jack Nicklaus golf course commu …more
$3,800,000
521 MUIRFIELD LOOP,

521 Muirfield Loop, Reunion

1215112482
NEW PRICE! Perfectly sited within the renowned gated community of the Reunion Re …more
$3,650,000

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