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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
Room

7BR Near Disney with Private Pool, Games and 4 King Suites

Vacation Home

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Osceola
7BR Near Disney with Private Pool, Games and 4 King Suites Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

7BR Near Disney with Private Pool, Games and 4 King Suites Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including an arcade/game room and charcoal grills.

7BR Near Disney with Private Pool, Games and 4 King Suites Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a desk and a coffee/tea maker.

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Sunlit Fun Lanai w/ Pool

Vacation Home

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Osceola
Sunlit Fun Lanai w/ Pool Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.6 mi (12.2 km) from Old Town.

Sunlit Fun Lanai w/ Pool Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including gas grills.

Sunlit Fun Lanai w/ Pool Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool. Conveniences include a separate sitting area and a washer/dryer.

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1410 Wexford Way

Vacation Home

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Osceola
1410 Wexford Way Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This family-friendly vacation home is 11.5 mi (18.6 km) from Old Town and 12.4 mi (20 km) from ESPN Wide World of Sports Complex.

1410 Wexford Way Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1410 Wexford Way Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony or patio. A flat-screen television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a coffee/tea maker.

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Bedroom

3236 TT Hub Townhome: 3br, 3ba, Sleeps 8

Vacation Home

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Osceola
3236 TT Hub Townhome: 3br, 3ba, Sleeps 8 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

3236 TT Hub Townhome: 3br, 3ba, Sleeps 8 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

3236 TT Hub Townhome: 3br, 3ba, Sleeps 8 Rooms
Make yourself comfortable in your vacation home.

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House with pool in resort

Vacation Home

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Osceola
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Paradise Palms Resort 6 Bedroom Home with Game Room 6 Home

Vacation Home

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Osceola
Paradise Palms Resort 6 Bedroom Home with Game Room 6 Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8.6 mi (13.9 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Paradise Palms Resort 6 Bedroom Home with Game Room 6 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

Flamingo Paradise

Vacation Home

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Osceola
Flamingo Paradise Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 6 mi (9.6 km) from Old Town and 6 mi (9.7 km) from ESPN Wide World of Sports Complex.

Flamingo Paradise Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private furnished patio. A 42-inch flat-screen television is provided, with digital programming available. Conveniences include a separate sitting area and a microwave.

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Sport & Beauty

Nautical by Nature

Private Vacation Home

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Osceola
Nautical by Nature Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 6.3 mi (10.2 km) from Old Town and 6.7 mi (10.8 km) from Disney's Hollywood Studios®.

Nautical by Nature 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. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Room

Home 6bed Themed Rooms Game Room Storey Lake

Vacation Home

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Osceola
Home 6bed Themed Rooms Game Room Storey Lake 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 6 mi (9.6 km) from Disney Springs™ and 6.9 mi (11.1 km) from Walt Disney World® Resort.

Home 6bed Themed Rooms Game Room Storey Lake Facility and Service
Take in the views from a garden.

Home 6bed Themed Rooms Game Room Storey Lake Rooms
Make yourself comfortable in your vacation home.

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Exterior & Views

4882rc

Vacation Home

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Osceola
4882rc Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.9 mi (9.5 km) from Disney Springs™ and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

4882rc Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4882rc Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a flat-screen TV. A kitchen is outfitted with a refrigerator and a microwave. Complimentary wired and wireless internet access is available.

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Sport & Beauty

Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning

Vacation Home

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Osceola
Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 10 minutes from Walt Disney World® Resort. This vacation home is 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.3 km) from Old Town.

Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning 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

Venetian Bay #103 - Three Bedroom Townhome

Private Vacation Home

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Osceola
Venetian Bay #103 - Three Bedroom Townhome Location
With a stay at this vacation home in Kissimmee (Venetian Bay Villages), you'll be within a 15-minute drive of Old Town and 192 Flea Market. This vacation home is 10 mi (16 km) from Disney Springs™ and 10.8 mi (17.4 km) from ESPN Wide World of Sports Complex.

Venetian Bay #103 - Three Bedroom Townhome Rooms
Make yourself comfortable in this vacation home, which features a private pool. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

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Others

5127 Crown Haven dr

Private Vacation Home

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Osceola
5127 Crown Haven dr Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 5-minute drive from Old Town and 10 minutes from Walt Disney World® Resort. This vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.7 km) from Disney's Hollywood Studios®.

5127 Crown Haven dr 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.

5127 Crown Haven dr Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. Conveniences include a microwave and a coffee/tea maker.

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Sport & Beauty

Berkeley Executive - Five Bedroom Home

Private Vacation Home

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Osceola
Berkeley Executive - Five Bedroom Home Location
With a stay at this vacation home in Kissimmee, you'll be steps from Remington Golf Club and a 3-minute drive from Osceola Center for the Arts. This vacation home is 13.4 mi (21.5 km) from Old Town and 14.2 mi (22.9 km) from Florida Mall.

Berkeley Executive - Five Bedroom Home Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Berkeley Executive - Five Bedroom Home Rooms
Make yourself comfortable in this vacation home, which features a private pool. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Complimentary wireless internet access is available to keep you connected.

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9043dd00

Vacation Home

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Osceola
9043dd00 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 villa is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

9043dd00 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional features at this villa include an arcade/game room and barbecue grills.

9043dd00 Rooms
Make yourself comfortable in this air-conditioned villa, which features a fireplace and a flat-screen TV. A kitchen is outfitted with a refrigerator and a microwave. Complimentary wired and wireless internet access is available.

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Others

4/3 Townhouse Near Disney!!

Vacation Home

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Osceola
4/3 Townhouse Near Disney!! Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.2 mi (11.6 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.3 km) from Old Town.

4/3 Townhouse Near Disney!! Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4/3 Townhouse Near Disney!! Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Bathroom

Lucaya 4 Bedrooms 4 Baths Townhome, Spacious Living Room

Vacation Home

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Osceola
Lucaya 4 Bedrooms 4 Baths Townhome, Spacious Living Room Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex.

Lucaya 4 Bedrooms 4 Baths Townhome, Spacious Living Room Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

Lucaya 4 Bedrooms 4 Baths Townhome, Spacious Living Room Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Conveniences include a microwave and a washing machine.

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Bedroom

Storey Lake 9BR Lakeview Home Pool/spa/game Disney

Vacation Home

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Osceola
Storey Lake 9BR Lakeview Home Pool/spa/game Disney Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.5 mi (12 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Storey Lake 9BR Lakeview Home Pool/spa/game Disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Storey Lake 9BR Lakeview Home Pool/spa/game Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Room

Kis105-2601-4-pg - Shingle Creek Poolside Retreat

Vacation Home

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Osceola
Kis105-2601-4-pg - Shingle Creek Poolside Retreat Location
With a stay at this vacation home in Kissimmee, you'll be near the beach, just steps from Shingle Creek Regional Park and a 5-minute drive from Kissimmee Sports Arena and Rodeo. This vacation home is 10.2 mi (16.4 km) from Old Town and 11.6 mi (18.7 km) from Orlando Vineland Premium Outlets.

Kis105-2601-4-pg - Shingle Creek Poolside Retreat Facility and Service
Enjoy recreational amenities such as an outdoor pool and a sauna.

Kis105-2601-4-pg - Shingle Creek Poolside Retreat Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Windsor at Westside Resort Homes

Vacation Home

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Osceola
Welcome To Windsor At Westside Resort, One Of The Most Popular Resort Communities In The Orlando AreaThe stunning Windsor at West Side vacation rentals resort community features all the popular resort amenities of its sister communities – Windsor Hills Resort and Windsor Palms Resort, AND more! This stunning vacation rental resort community features an extraordinary 10, 000 sq. ft. clubhouse with:* Huge resort-style pool* Tu Casa (full-service restaurant)* Interactive children's splash park with water slide* Firepit* State-of-the-art fitness* Sand volleyball court* Multi-purpose sports courts* Sundry shop* Ice cream parlor* Video arcade
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Vacation Homes in Osceola

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