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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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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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Spacious Family Retreat w/ Game Room & Steps to Clubhouse

Vacation Home

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Osceola
Spacious Family Retreat w/ Game Room & Steps to Clubhouse Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Spacious Family Retreat w/ Game Room & Steps to Clubhouse Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Spacious Family Retreat w/ Game Room & Steps to Clubhouse Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Spacious Home W/private Pool, Hot Tub & Game Room Near Disney

Vacation Home

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Osceola
Spacious Home W/private Pool, Hot Tub & Game Room Near Disney Location
Located in Kissimmee (Indian Ridge), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.5 km) from Old Town.

Spacious Home W/private Pool, Hot Tub & Game Room Near Disney Facility and Service
Take advantage of recreation 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.

Spacious Home W/private Pool, Hot Tub & Game Room Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Spacious Comfy Retreat Prime Location Amazing

Vacation Home

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Osceola
Spacious Comfy Retreat Prime Location Amazing 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 7.3 mi (11.7 km) from Disney Springs™ and 8.3 mi (13.4 km) from Walt Disney World® Resort.

Spacious Comfy Retreat Prime Location Amazing Facility and Service
Take in the views from a garden and make use of amenities such as barbecue grills.

Spacious Comfy Retreat Prime Location Amazing Rooms
Make yourself comfortable in your vacation home.

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5 Bedroom Home 8 Minutes To Disney! townhouse

Vacation Home

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Osceola
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Stunning Modern Home!

Vacation Home

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Osceola
Stunning Modern Home! 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 mi (11.3 km) from Disney Springs™ and 8 mi (13 km) from Walt Disney World® Resort.

Stunning Modern Home! 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.

Stunning Modern Home! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Shake Shack Heated Pool & Hot Tub

Vacation Home

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Osceola
Shake Shack Heated Pool & Hot Tub 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 5.8 mi (9.3 km) from Old Town and 6.4 mi (10.3 km) from ESPN Wide World of Sports Complex.

Shake Shack Heated Pool & Hot Tub Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Shake Shack Heated Pool & Hot Tub 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 patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 42-inch flat-screen television is provided, with digital programming available.

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5.0/5
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Others

1620mc-the Retreat at Championsgate

Vacation Home

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Osceola
1620mc-the Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 11.2 mi (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

1620mc-the Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1620mc-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Others

Lakeview Home Sleeps 25

Vacation Home

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Osceola
Lakeview Home Sleeps 25 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 mi (11.3 km) from Disney Springs™ and 8 mi (13 km) from Walt Disney World® Resort.

Lakeview Home Sleeps 25 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.

Lakeview Home Sleeps 25 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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South-Facing Pool 5BR Storey Lake Lazy River 2437

Vacation Home

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Osceola
South-Facing Pool 5BR Storey Lake Lazy River 2437 Location
With a stay at South-Facing Pool 5BR Storey Lake Lazy River 2437 in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.4 mi (12 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

South-Facing Pool 5BR Storey Lake Lazy River 2437 Rooms
Make yourself at home in one of the guestrooms, featuring kitchens with ovens and stovetops.

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5.0/5
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Private pool

Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020

Vacation Home

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Osceola
Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020 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 family-friendly vacation home is 12.2 mi (19.6 km) from Old Town and 13 mi (20.8 km) from ESPN Wide World of Sports Complex.

Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020 Facility and Service
Enjoy a range of recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a DVD player and cable programming provide entertainment. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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Sport & Beauty

Murano Mews

Vacation Home

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Osceola
Murano Mews Location
When you stay at this vacation home in Kissimmee, you'll be near the airport, within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.5 mi (13.7 km) from Disney's Animal Kingdom® Theme Park and 9.4 mi (15.1 km) from ESPN Wide World of Sports Complex.

Murano Mews Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. This vacation home also features an arcade/game room and charcoal grills.

Murano Mews Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and an outdoor private hot tub. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave, as well as a phone with free local calls.

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Food & Drinks

New! Luxury 12br Disney Home Pool/spa/cinema/games

Private Vacation Home

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Osceola
New! Luxury 12br Disney Home Pool/spa/cinema/games Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Disney Springs™. This vacation home is 8.3 mi (13.3 km) from Walt Disney World® Resort and 8.4 mi (13.6 km) from Disney's Hollywood Studios®.

New! Luxury 12br Disney Home Pool/spa/cinema/games Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a 24-hour fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

New! Luxury 12br Disney Home Pool/spa/cinema/games 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

8957-HiltonRidge

Vacation Home

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Osceola
8957-HiltonRidge Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10 mi (16.1 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

8957-HiltonRidge 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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Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly

Vacation Home

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Osceola
Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Orlando Vineland Premium Outlets and Old Town. This vacation home is 10.1 mi (16.3 km) from Disney Springs™ and 10.6 mi (17.1 km) from Orange County Convention Center.

Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly 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.

Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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5.0/5
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Dog-friendly Home w/ Private Pool, High-speed Wifi, and Central AC

Vacation Home

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Osceola
Dog-friendly Home w/ Private Pool, High-speed Wifi, and Central AC Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 3-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex and 6.2 mi (9.9 km) from Old Town.

Dog-friendly Home w/ Private Pool, High-speed Wifi, and Central AC 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.

Dog-friendly Home w/ Private Pool, High-speed Wifi, and Central AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Living area

Solara Resort 5 Bedroom Private Pool + Spa Home 5 Home

Vacation Home

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Osceola
Solara Resort 5 Bedroom Private Pool + Spa Home 5 Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Solara Resort 5 Bedroom Private Pool + Spa 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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Newly Built Townhome, Private W/d, Free Wifi, Central AC and Full Kitchen

Vacation Home

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Osceola
Newly Built Townhome, Private W/d, Free Wifi, Central AC and Full Kitchen 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 Flamingo Crossings Town Center. This vacation home is 6.7 mi (10.8 km) from Disney's Animal Kingdom® Theme Park and 7.9 mi (12.7 km) from Old Town.

Newly Built Townhome, Private W/d, Free Wifi, Central AC and Full Kitchen Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Nearby Landmark

4 Bedroom SunHaven Townhouse with Pool Near Disney

Vacation Home

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Osceola
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Exterior & Views

8911sydney

Vacation Home

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Osceola
8911sydney 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 family-friendly vacation home is 8.7 mi (14 km) from Walt Disney World® Resort and 10.5 mi (16.9 km) from Disney's Animal Kingdom® Theme Park.

8911sydney Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

8911sydney Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a private pool. A kitchen is outfitted with a refrigerator and a microwave. An LCD television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Vacation Homes in Osceola

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