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Vacation Homes in Osceola

Osceola
Fri, 13 Nov 2026 - Sat, 14 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Sleek Home With Stunning Game Room at Reunion

Private Vacation Home

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Osceola
Sleek Home With Stunning Game Room at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This family-friendly vacation home is 7 mi (11.3 km) from Walt Disney World® Resort and 9 mi (14.5 km) from Old Town.

Sleek Home With Stunning Game Room at Reunion Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

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

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Cozy Home Storey Lake Resort Pool Spa Near Disney

Vacation Home

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Osceola
Cozy Home Storey Lake Resort Pool Spa Near Disney 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 6.2 mi (10 km) from Disney Springs™ and 7.2 mi (11.5 km) from ESPN Wide World of Sports Complex.

Cozy Home Storey Lake Resort Pool Spa Near Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor tennis court, or other amenities including complimentary wireless internet access and an arcade/game room.

Cozy Home Storey Lake Resort Pool Spa Near 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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Magical Sunny Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Magical Sunny Townhouse With Games Room at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This golf vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14.1 km) from Old Town.

Magical Sunny Townhouse With Games Room at Reunion Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access and an arcade/game room.

Magical Sunny Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Modern 6 Bedroom Home With Upscale Living at Reunion

Vacation Home

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Osceola
Modern 6 Bedroom Home With Upscale Living 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 7.8 mi (12.5 km) from Walt Disney World® Resort and 9.8 mi (15.7 km) from Old Town.

Modern 6 Bedroom Home With Upscale Living at Reunion Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Modern 6 Bedroom Home With Upscale Living at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi

Vacation Home

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Osceola
Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 4.9 mi (7.8 km) from ESPN Wide World of Sports Complex and 5.7 mi (9.2 km) from Disney's Hollywood Studios®.

Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi Facility and Service
Be sure to enjoy recreational amenities including an outdoor tennis court and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Oi2836 - 4BR House With Pool Near Disney World

Private Vacation Home

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Osceola
Oi2836 - 4BR House With Pool Near Disney World Location
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 6 mi (9.7 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Oi2836 - 4BR House With Pool Near Disney World Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Oi2836 - 4BR House With Pool Near Disney World 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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Magic Moments Getaway

Vacation Home

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Osceola
Magic Moments Getaway 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 vacation home is 7.4 mi (11.9 km) from Walt Disney World® Resort and 9.6 mi (15.5 km) from ESPN Wide World of Sports Complex.

Magic Moments Getaway Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Magic Moments Getaway Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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View from room

Close 5min to Disney Fantastic Townhome BBQ 152

Vacation Home

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Osceola
Close 5min to Disney Fantastic Townhome BBQ 152 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.8 mi (7.8 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.9 km) from Disney's Hollywood Studios®.

Close 5min to Disney Fantastic Townhome BBQ 152 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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3 Br 2 Miles To Disney, Pool, Free Wifi And More 3 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
3 Br 2 Miles To Disney, Pool, Free Wifi And More 3 Bedroom Townhouse by RedAwning 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 vacation home is 6 mi (9.6 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.9 km) from Disney's Hollywood Studios®.

3 Br 2 Miles To Disney, Pool, Free Wifi And More 3 Bedroom Townhouse by RedAwning 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.

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Beautiful Paradise Palms Retreat 4 Bedroom Townhouse

Vacation Home

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Osceola
Beautiful Paradise Palms Retreat 4 Bedroom Townhouse 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 vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 5.9 mi (9.4 km) from Walt Disney World® Resort.

Beautiful Paradise Palms Retreat 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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Beautiful 3 Bdrm 2 Bath Condo

Vacation Home

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Osceola
Beautiful 3 Bdrm 2 Bath Condo Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 5.7 mi (9.1 km) from Disney Springs™ and 6.7 mi (10.8 km) from Walt Disney World® Resort.

Beautiful 3 Bdrm 2 Bath Condo Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and barbecue grills.

Beautiful 3 Bdrm 2 Bath Condo Rooms
Make yourself comfortable in this condo, which has a kitchen. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Solara Resort 6 Bedroom Private Pool Home 6 Home

Vacation Home

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Osceola
Solara Resort 6 Bedroom Private Pool Home 6 Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.5 mi (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Solara Resort 6 Bedroom Private Pool Home 6 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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Spacious Home With Game Room and Mickey Shaped Pool and gas Grill

Vacation Home

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Osceola
Spacious Home With Game Room and Mickey Shaped Pool and gas Grill Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 5-minute drive of Mystic Dunes Golf Club and Island H2O Live!. This family-friendly vacation home is 2.6 mi (4.1 km) from Walt Disney World® Resort and 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex.

Spacious Home With Game Room and Mickey Shaped Pool and gas Grill 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.

Spacious Home With Game Room and Mickey Shaped Pool and gas Grill Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Huge Family Home! Sleeps 26!

Vacation Home

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Osceola
Huge Family Home! Sleeps 26! 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 7.3 mi (11.7 km) from Disney Springs™ and 8.3 mi (13.4 km) from Walt Disney World® Resort.

Huge Family Home! Sleeps 26! Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including an arcade/game room and barbecue grills.

Huge Family Home! Sleeps 26! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Family-friendly Home With Pool & Movie Theater

Vacation Home

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Osceola
Family-friendly Home With Pool & Movie Theater Location
With a stay at this vacation home in Four Corners, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.1 mi (19.4 km) from Old Town and 12.6 mi (20.4 km) from Walt Disney World® Resort.

Family-friendly Home With Pool & Movie Theater Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Family-friendly Home With Pool & Movie Theater 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.

See details
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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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Magic Lily - Storey Lake By Shine Villas #834 4 Bedroom Townhouse

Vacation Home

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Osceola
Magic Lily - Storey Lake By Shine Villas #834 4 Bedroom Townhouse Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 7 mi (11.2 km) from Disney Springs™ and 8.1 mi (13 km) from Walt Disney World® Resort.

Magic Lily - Storey Lake By Shine Villas #834 4 Bedroom Townhouse Facility and Service
Enjoy recreational amenities such as an outdoor tennis court and a fitness center.

Magic Lily - Storey Lake By Shine Villas #834 4 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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2.0/5
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Upstay - Theater Games Sleeps 16 Pool

Vacation Home

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Osceola
Upstay - Theater Games Sleeps 16 Pool Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.2 mi (16.4 km) from ESPN Wide World of Sports Complex and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Upstay - Theater Games Sleeps 16 Pool Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an indoor pool.

Upstay - Theater Games Sleeps 16 Pool 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.

See details
4.0/5
Fully Booked
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Dog-friendly Retreat With hot Tub, Outdoor Pool, & Tennis Court - Great Location

Vacation Home

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Osceola
Dog-friendly Retreat With hot Tub, Outdoor Pool, & Tennis Court - Great Location 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 7.5 mi (12 km) from Disney Springs™ and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Dog-friendly Retreat With hot Tub, Outdoor Pool, & Tennis Court - Great Location Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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Vacation Homes in Osceola

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