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Vacation Homes in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Luxury Townhome - Resort Amenities

Vacation Home

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Osceola
Luxury Townhome - Resort Amenities Location
With a stay at this vacation home in Kissimmee, you'll be a 1-minute drive from Old Town and 9 minutes from Walt Disney World® Resort. This vacation home is 4.7 mi (7.6 km) from ESPN Wide World of Sports Complex and 4.8 mi (7.7 km) from Disney's Hollywood Studios®.

Luxury Townhome - Resort Amenities Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board, and housekeeping is provided on request.

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Grand Panoramic 3BR Townhouse Near Disney

Vacation Home

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Osceola
Grand Panoramic 3BR Townhouse Near Disney 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 5.9 mi (9.5 km) from Walt Disney World® Resort.

Grand Panoramic 3BR Townhouse Near Disney Facility and Service
Take in the views from a garden.

Grand Panoramic 3BR Townhouse Near Disney Rooms
Make yourself comfortable in your vacation home.

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Dream 5Bd Storeylake Close to Disney

Vacation Home

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Osceola
Dream 5Bd Storeylake Close to Disney 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 7.4 mi (11.9 km) from Disney Springs™ and 8.1 mi (13 km) from Walt Disney World® Resort.

Dream 5Bd Storeylake Close to Disney Rooms
Make yourself comfortable in your vacation home.

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Room

Go 22 Paddington Way

Vacation Home

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Osceola
Go 22 Paddington Way Location
Located in Kissimmee (Lindfields), this vacation home is within a 10-minute drive of Mystic Dunes Golf Club and Flamingo Crossings Town Center. This vacation home is 5 mi (8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from Old Town.

Go 22 Paddington Way Rooms
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Charming 4BR Home Near Disney Bella Vida

Vacation Home

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Osceola
Charming 4BR Home Near Disney Bella Vida Location
With a stay at this vacation home in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.5 mi (13.6 km) from Disney Springs™ and 8.9 mi (14.3 km) from Walt Disney World® Resort.

Charming 4BR Home Near Disney Bella Vida Rooms
Make yourself comfortable in your vacation home.

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Quiet Resort 3BR Nature Walk 20min to Disney

Vacation Home

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Osceola
Quiet Resort 3BR Nature Walk 20min to 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 9 mi (14.4 km) from Disney Springs™ and 9.1 mi (14.7 km) from Walt Disney World® Resort.

Quiet Resort 3BR Nature Walk 20min to Disney Rooms
Make yourself comfortable in your vacation home.

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Luxury Compass 3BR Townhouse Near Disney Parks 2

Vacation Home

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Osceola
Luxury Compass 3BR Townhouse Near Disney Parks 2 Location
With a stay at this apartment in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This apartment is 5.2 mi (8.3 km) from Disney Springs™ and 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex.

Luxury Compass 3BR Townhouse Near Disney Parks 2 Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Luxury Compass 3BR Townhouse Near Disney Parks 2 Rooms
Make yourself comfortable in your apartment.

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Others

Welcome to Your Family Luxurious Calabria Villa

Vacation Home

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Osceola
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Amazing 6Bd Pool Gameroom Verandapalms

Vacation Home

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Osceola
Amazing 6Bd Pool Gameroom Verandapalms 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 6.9 mi (11.1 km) from Disney Springs™ and 7.9 mi (12.8 km) from Walt Disney World® Resort.

Amazing 6Bd Pool Gameroom Verandapalms Rooms
Make yourself comfortable in your vacation home.

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Storeylake 9Bd Pooltable Cinema Games Pool

Vacation Home

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Osceola
Storeylake 9Bd Pooltable Cinema Games Pool 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 spa vacation home is 6.2 mi (10 km) from Disney Springs™ and 6.9 mi (11.1 km) from Walt Disney World® Resort.

Storeylake 9Bd Pooltable Cinema Games Pool Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

Storeylake 9Bd Pooltable Cinema Games Pool Rooms
Make yourself comfortable in your vacation home.

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5bedrooms Private Pool Storeylake

Vacation Home

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Osceola
5bedrooms Private Pool Storeylake 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 (8.9 km) from Disney Springs™ and 6.5 mi (10.5 km) from Walt Disney World® Resort.

5bedrooms Private Pool Storeylake Rooms
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Others

Family Getaway 4BR Townhome by Old Town

Vacation Home

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Osceola
Family Getaway 4BR Townhome by Old Town Location
With a stay at this vacation home in Kissimmee, you'll be a 1-minute drive from Old Town and 9 minutes from Walt Disney World® Resort. This vacation home is 4.4 mi (7.2 km) from ESPN Wide World of Sports Complex and 4.6 mi (7.5 km) from Disney's Hollywood Studios®.

Family Getaway 4BR Townhome by Old Town Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a shower.Conveniences include a washing machine and an iron/ironing board.

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Grand Emerald Island 3BR Townhouse Near Disney

Vacation Home

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Osceola
Grand Emerald Island 3BR Townhouse Near Disney Location
With a stay at this apartment in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This apartment is 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex and 6.8 mi (11 km) from Old Town.

Grand Emerald Island 3BR Townhouse Near Disney Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Grand Emerald Island 3BR Townhouse Near Disney Rooms
Make yourself comfortable in your apartment.

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Grand Resort 3BR Compass Townhouse Near Disney 1

Vacation Home

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Osceola
Grand Resort 3BR Compass Townhouse Near Disney 1 Location
With a stay at this apartment in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This apartment is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.6 km) from Walt Disney World® Resort.

Grand Resort 3BR Compass Townhouse Near Disney 1 Rooms
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Go 27 - Champions Gate

Vacation Home

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Osceola
Go 27 - Champions Gate Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.3 mi (19.8 km) from Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

Go 27 - Champions Gate Facility and Service
This vacation home offers a stereo.

Go 27 - Champions Gate Rooms
Make yourself comfortable in your vacation home.

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Luxury 9BD Encore Pool Summerkitchen

Vacation Home

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Osceola
Luxury 9BD Encore Pool Summerkitchen Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. 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.

Luxury 9BD Encore Pool Summerkitchen Rooms
Make yourself comfortable in your vacation home.

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Wonderful 6bd 5bat w Golf Course Championsgate

Vacation Home

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Osceola
Wonderful 6bd 5bat w Golf Course Championsgate Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12.4 mi (20 km) from Old Town and 13 mi (20.9 km) from ESPN Wide World of Sports Complex.

Wonderful 6bd 5bat w Golf Course Championsgate Rooms
Make yourself comfortable in your vacation home.

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NEW Home Storeylake 4Bd 3 Walking Clubhouse

Vacation Home

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Osceola
NEW Home Storeylake 4Bd 3 Walking Clubhouse 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 7.2 mi (11.6 km) from Disney Springs™ and 8.2 mi (13.3 km) from Walt Disney World® Resort.

NEW Home Storeylake 4Bd 3 Walking Clubhouse Rooms
Make yourself comfortable in your vacation home.

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Luxury Home With Pool Game Room Cinema

Vacation Home

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Osceola
Luxury Home With Pool Game Room Cinema Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 7.9 mi (12.7 km) from Walt Disney World® Resort and 9.5 mi (15.4 km) from Disney's Animal Kingdom® Theme Park.

Luxury Home With Pool Game Room Cinema Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

Luxury Home With Pool Game Room Cinema Rooms
Make yourself comfortable in your vacation home.

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Exterior & Views

Storey Lake 3121-204: 2BR Condo, Sleeps 6

Vacation Home

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Osceola
Storey Lake 3121-204: 2BR Condo, Sleeps 6 Location
With a stay at this apartment in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This apartment is 5.8 mi (9.3 km) from Disney Springs™ and 6.8 mi (10.9 km) from Walt Disney World® Resort.

Storey Lake 3121-204: 2BR Condo, Sleeps 6 Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and an arcade/game room.

Storey Lake 3121-204: 2BR Condo, Sleeps 6 Rooms
Make yourself comfortable in your apartment. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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Vacation Homes in Osceola

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