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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Exterior & Views

9 Bedrooms S / Storey Lake Home by RedAwning

Vacation Home

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Osceola
9 Bedrooms S / Storey Lake Home 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 6.2 mi (9.9 km) from Disney Springs™ and 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex.

9 Bedrooms S / Storey Lake 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.

9 Bedrooms S / Storey Lake Home by RedAwning Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a microwave. Complimentary wireless internet access is available to keep you connected.

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Championsgate Resort 6 Bedroom Private Pool Home 6 Home

Vacation Home

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Osceola
Championsgate Resort 6 Bedroom Private Pool Home 6 Home 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 Mystic Dunes Golf Club. This vacation home is 11.5 mi (18.5 km) from Old Town and 12.1 mi (19.4 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 6 Bedroom Private Pool Home 6 Home 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. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Others

Perfect for Children! With Epic Themed Bedrooms

Vacation Home

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Osceola
Perfect for Children! With Epic Themed Bedrooms Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.5 mi (13.6 km) from Walt Disney World® Resort and 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park.

Perfect for Children! With Epic Themed Bedrooms Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Perfect for Children! With Epic Themed Bedrooms Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Updated & Colorful Home w/ a Modern Kitchen, Furnished Lanai, & Private Pool

Vacation Home

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Osceola
Updated & Colorful Home w/ a Modern Kitchen, Furnished Lanai, & Private Pool Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, 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 10.9 mi (17.5 km) from ESPN Wide World of Sports Complex.

Updated & Colorful Home w/ a Modern Kitchen, Furnished Lanai, & Private Pool Facility and Service
Enjoy a range of recreational amenities, including a hot tub, an outdoor tennis court, and a fitness center.

Updated & Colorful Home w/ a Modern Kitchen, Furnished Lanai, & Private Pool Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Four Bedroom close to Disney w/ Pool 4898

Vacation Home

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Osceola
Four Bedroom close to Disney w/ Pool 4898 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6.3 mi (10.2 km) from Walt Disney World® Resort.

Four Bedroom close to Disney w/ Pool 4898 Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and an indoor pool. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Four Bedroom close to Disney w/ Pool 4898 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. 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 flat-screen television with cable programming provides entertainment.

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4.6/5
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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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Beautiful Tranquil Relaxing Home With Private Pool 4 Bedroom Townhouse

Vacation Home

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Osceola
Beautiful Tranquil Relaxing Home With Private Pool 4 Bedroom Townhouse 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Beautiful Tranquil Relaxing Home With Private Pool 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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Magical Family Getaway 10ppl

Vacation Home

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Osceola
Magical Family Getaway 10ppl Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This vacation home is 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex and 7 mi (11.2 km) from Old Town.

Magical Family Getaway 10ppl 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 and an arcade/game room.

Magical Family Getaway 10ppl 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 42-inch flat-screen television is provided, with digital programming available. A private bathroom has a deep soaking tub.

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Sport & Beauty

Storey Lake Resort, Private Pool, and Much More!!

Private Vacation Home

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Osceola
Storey Lake Resort, Private Pool, and Much More!! 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 6.3 mi (10.1 km) from Disney Springs™ and 7.2 mi (11.7 km) from ESPN Wide World of Sports Complex.

Storey Lake Resort, Private Pool, and Much More!! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Storey Lake Resort, Private Pool, and Much More!! 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

8941 Bismark Palm rd

Private Vacation Home

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Osceola
8941 Bismark Palm rd Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This golf vacation home is 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.2 mi (13.2 km) from Disney's Animal Kingdom® Theme Park.

8941 Bismark Palm rd Facility and Service
Be sure to enjoy recreational amenities, including an indoor pool, an outdoor tennis court, and a fitness center.

8941 Bismark Palm rd Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Exterior & Views

Star Wars 7 Bed Pool Home With Game Room 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
Star Wars 7 Bed Pool Home With Game Room 7 Bedroom Home by RedAwning 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 11.8 mi (18.9 km) from Old Town and 12.6 mi (20.2 km) from ESPN Wide World of Sports Complex.

Star Wars 7 Bed Pool Home With Game Room 7 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Sport & Beauty

1575mvd-the Retreat at Championsgate

Vacation Home

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Osceola
1575mvd-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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

1575mvd-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center.

1575mvd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Room

Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24

Vacation Home

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Osceola
Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.3 mi (10.1 km) from Disney Springs™ and 7.3 mi (11.8 km) from Walt Disney World® Resort.

Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24 Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a hot tub, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor at Westside Resort 8 Bedroom Pool+Spa Home 8 Home

Vacation Home

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Osceola
Windsor at Westside Resort 8 Bedroom Pool+Spa Home 8 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 (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Windsor at Westside Resort 8 Bedroom Pool+Spa Home 8 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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Exterior & Views

3 Bed/2.5 Bath Perfect Family Home Bunk Beds 3 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
3 Bed/2.5 Bath Perfect Family Home Bunk Beds 3 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7 mi (11.2 km) from Disney's Animal Kingdom® Theme Park and 8.2 mi (13.2 km) from ESPN Wide World of Sports Complex.

3 Bed/2.5 Bath Perfect Family Home Bunk Beds 3 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Spd2326 3 Bedroom Townhouse

Vacation Home

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Osceola
Spd2326 3 Bedroom Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex and 8.2 mi (13.2 km) from Disney's Hollywood Studios®.

Spd2326 3 Bedroom Townhouse 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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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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Exterior & Views

Greenview 8BR Home Private Theater Pool/spa/games

Vacation Home

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Osceola
Greenview 8BR Home Private Theater Pool/spa/games 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 11.2 mi (18 km) from Old Town and 11.9 mi (19.2 km) from ESPN Wide World of Sports Complex.

Greenview 8BR Home Private Theater Pool/spa/games 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.

Greenview 8BR Home Private Theater Pool/spa/games Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower.

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5.0/5
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2-story Townhouse Near Disney W/private Heated Pool, Shared Clubhouse, Gym, AC

Vacation Home

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Osceola
2-story Townhouse Near Disney W/private Heated Pool, Shared Clubhouse, Gym, AC Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 5.8 mi (9.4 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

2-story Townhouse Near Disney W/private Heated Pool, Shared Clubhouse, Gym, AC Facility and Service
Enjoy recreational amenities such as an outdoor tennis court and a fitness center.

2-story Townhouse Near Disney W/private Heated Pool, Shared Clubhouse, Gym, AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
3.0/5
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Sport & Beauty

Paradise Palms-5 Bed Townhome W/splashpool-3045pp 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Paradise Palms-5 Bed Townhome W/splashpool-3045pp 5 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (14.9 km) from ESPN Wide World of Sports Complex.

Paradise Palms-5 Bed Townhome W/splashpool-3045pp 5 Bedroom Townhouse by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including complimentary wireless internet access.

Paradise Palms-5 Bed Townhome W/splashpool-3045pp 5 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this vacation home, which features a private pool and a flat-screen TV. There's a private furnished lanai. A kitchen is outfitted with a refrigerator and a dishwasher. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment.

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Vacation Homes in Osceola

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