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Vacation Homes in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Sport & Beauty

Gated Community, Private Pool and Game Room Near Disney!!!

Vacation Home

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Osceola
Gated Community, Private Pool and Game Room Near Disney!!! Location
With a stay at this vacation home in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.1 mi (13 km) from Disney Springs™ and 8.3 mi (13.4 km) from Walt Disney World® Resort.

Gated Community, Private Pool and Game Room Near Disney!!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Others

1521fd - The Retreat at Championsgate

Vacation Home

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Osceola
1521fd - The Retreat at Championsgate Location
With a stay at this villa in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf villa is 11.2 mi (18 km) from Old Town and 12 mi (19.2 km) from ESPN Wide World of Sports Complex.

1521fd - The Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. This villa also features an arcade/game room and barbecue grills.

1521fd - The Retreat at Championsgate Rooms
Make yourself comfortable in your air-conditioned villa, which features a flat-screen TV.

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Room

Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A

Vacation Home

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Osceola
Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.4 mi (8.6 km) from Disney Springs™ and 6 mi (9.7 km) from Walt Disney World® Resort.

Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a 60-inch Smart television with cable programming provides entertainment.

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3.7/5
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Windsor Hills Resort 5 Bedroom Updated Pool Home 5 Home

Vacation Home

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Osceola
Windsor Hills Resort 5 Bedroom Updated Pool Home 5 Home Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 5.3 mi (8.5 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Windsor Hills Resort 5 Bedroom Updated Pool Home 5 Home Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Others

Home & Storey Lake Water 5br/5ba - Park Amenities

Private Vacation Home

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Osceola
Home & Storey Lake Water 5br/5ba - Park Amenities Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.4 mi (11.8 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Home & Storey Lake Water 5br/5ba - Park Amenities Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and an arcade/game room.

Home & Storey Lake Water 5br/5ba - Park Amenities Rooms
Make yourself comfortable in your individually decorated vacation home.

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Bedroom

20 Guest Family Mansion at Sonoma Resort

Vacation Home

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Osceola
20 Guest Family Mansion at Sonoma Resort Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.5 mi (15.3 km) from Disney Springs™ and 10.2 mi (16.5 km) from Walt Disney World® Resort.

20 Guest Family Mansion at Sonoma Resort Facility and Service
Take advantage of recreation opportunities such as an indoor pool, or other amenities including complimentary wireless internet access and gas grills.

20 Guest Family Mansion at Sonoma Resort Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected.

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Paradise Falls - Stay for 13

Vacation Home

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Osceola
Paradise Falls - Stay for 13 Location
With a stay at this vacation home in Kissimmee (Veranda Palms), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This luxury vacation home is 7 mi (11.3 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Paradise Falls - Stay for 13 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Paradise Falls - Stay for 13 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and an outdoor private hot tub. There's a private furnished lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 65-inch flat-screen television is provided, with digital programming available.

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Cg1569 - 5BR House With Pool Near Disney Parks

Vacation Home

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Osceola
Cg1569 - 5BR House With Pool Near Disney Parks Location
With a stay at this cottage in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This cottage is 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Cg1569 - 5BR House With Pool Near Disney Parks Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Cg1569 - 5BR House With Pool Near Disney Parks Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private patio. Conveniences include a microwave and a washer/dryer.

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Game room

Stunning 5 Bd Home w/ Pool Close to Disney 7420

Vacation Home

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Osceola
Stunning 5 Bd Home w/ Pool Close to Disney 7420 Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This luxury vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.7 mi (15.7 km) from ESPN Wide World of Sports Complex.

Stunning 5 Bd Home w/ Pool Close to Disney 7420 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this vacation home include concierge services, a television in a common area, and charcoal grills.

Stunning 5 Bd Home w/ Pool Close to Disney 7420 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A 60-inch Smart television with cable programming provides entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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3.7/5
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Sport & Beauty

4832rc 4 Bedroom Townhouse by Redawning

Vacation Home

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Osceola
4832rc 4 Bedroom Townhouse by Redawning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 5.5 mi (8.8 km) from Disney Springs™ and 6.5 mi (10.5 km) from Walt Disney World® Resort.

4832rc 4 Bedroom Townhouse by Redawning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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Colorful 10br at Encore, 10 Min to Disney

Vacation Home

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Osceola
Colorful 10br at Encore, 10 Min to Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 5.5 mi (8.9 km) from Walt Disney World® Resort and 7.8 mi (12.5 km) from ESPN Wide World of Sports Complex.

Colorful 10br at Encore, 10 Min to Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Colorful 10br at Encore, 10 Min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Reunion Retreat 3 Bedroom Home by RedAwning

Vacation Home

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Osceola
Reunion Retreat 3 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 2-minute drive from Reunion Resort Golf Course and 6 minutes from ChampionsGate Golf Club. This vacation home is 8 mi (12.9 km) from Walt Disney World® Resort and 9.7 mi (15.6 km) from Old Town.

Reunion Retreat 3 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Others

1233chd - The Retreat At Championsgate 9 Bedroom Home by RedAwning

Vacation Home

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Osceola
1233chd - The Retreat At Championsgate 9 Bedroom Home by RedAwning Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

1233chd - The Retreat At Championsgate 9 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Bright Home With Game Room Theater at Reunion

Vacation Home

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Osceola
Bright Home With Game Room Theater at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 7.4 mi (11.9 km) from Walt Disney World® Resort and 9.4 mi (15.2 km) from Old Town.

Bright Home With Game Room Theater at Reunion Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

Bright Home With Game Room Theater at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Stunning 4 Bed Townhome With Splash Pool-1160ks 4 Bedroom Townhouse

Vacation Home

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Osceola
Stunning 4 Bed Townhome With Splash Pool-1160ks 4 Bedroom Townhouse Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.5 km) from ESPN Wide World of Sports Complex.

Stunning 4 Bed Townhome With Splash Pool-1160ks 4 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Living area

Windsor Palms Resort Vacation Home Wp2209

Vacation Home

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Osceola
Windsor Palms Resort Vacation Home Wp2209 Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.6 km) from Disney's Hollywood Studios®.

Windsor Palms Resort Vacation Home Wp2209 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Conveniences include a dryer and an iron/ironing board.

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Interior

ChampionsGate 9 Bedroom Pool Home with Game Room 9 Home

Vacation Home

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Osceola
ChampionsGate 9 Bedroom Pool Home with Game Room 9 Home Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.8 mi (19 km) from Old Town and 12.6 mi (20.2 km) from ESPN Wide World of Sports Complex.

ChampionsGate 9 Bedroom Pool Home with Game Room 9 Home Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a coffee/tea maker and a washing machine.

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Room

Kissimmee Oasis 4BR House Pool & Sleeps 8

Vacation Home

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Osceola
Kissimmee Oasis 4BR House Pool & Sleeps 8 Location
Located in Kissimmee, this vacation home is in the entertainment district, within a 10-minute drive of Shingle Creek Regional Park and Green Meadows Petting Farm. This vacation home is 12.3 mi (19.9 km) from Old Town and 14.6 mi (23.4 km) from Orlando Vineland Premium Outlets.

Kissimmee Oasis 4BR House Pool & Sleeps 8 Facility and Service
Enjoy recreation amenities such as a seasonal outdoor pool or take in the view from a garden.

Kissimmee Oasis 4BR House Pool & Sleeps 8 Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Sport & Beauty

Ov2681 - Windsor Hills Resort - 3 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov2681 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 5.6 mi (8.9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov2681 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2681 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Others

Good Times at Tuscana 2 BDR

Vacation Home

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Osceola
Good Times at Tuscana 2 BDR Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be a 5-minute drive from ChampionsGate Golf Club and 8 minutes from Reunion Resort Golf Course. This vacation home is 9 mi (14.5 km) from Walt Disney World® Resort and 9.2 mi (14.8 km) from Old Town.

Good Times at Tuscana 2 BDR Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and complimentary use of a nearby fitness facility.

Good Times at Tuscana 2 BDR Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Digital television is provided for your entertainment. Conveniences include a separate sitting area and a microwave.

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Vacation Homes in Osceola

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