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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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Lovely Family Townhome In Great Location-2200scd 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Lovely Family Townhome In Great Location-2200scd 4 Bedroom Townhouse by RedAwning 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 Orlando Vineland Premium Outlets. This vacation home is 9.3 mi (15 km) from Disney Springs™ and 10.4 mi (16.7 km) from Walt Disney World® Resort.

Lovely Family Townhome In Great Location-2200scd 4 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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Dog-friendly Home With a Heated Pool, Pool Spa, In-home Theater, Lanai, & Patio

Vacation Home

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Osceola
Dog-friendly Home With a Heated Pool, Pool Spa, In-home Theater, Lanai, & Patio Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Disney Springs™ and Disney's Typhoon Lagoon Water Park. This vacation home is 9.5 mi (15.2 km) from ESPN Wide World of Sports Complex and 9.7 mi (15.6 km) from Walt Disney World® Resort.

Dog-friendly Home With a Heated Pool, Pool Spa, In-home Theater, Lanai, & Patio Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Dog-friendly Home With a Heated Pool, Pool Spa, In-home Theater, Lanai, & Patio Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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3.0/5
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Others

Grhmll1573 - Champions Gate Resort - 5 Bed 5 Baths House

Vacation Home

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Osceola
Grhmll1573 - Champions Gate Resort - 5 Bed 5 Baths House 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 family-friendly vacation home is 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Grhmll1573 - Champions Gate Resort - 5 Bed 5 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmll1573 - Champions Gate Resort - 5 Bed 5 Baths House Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

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The Serenity Townhome

Vacation Home

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Osceola
The Serenity Townhome 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 vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14.1 km) from Old Town.

The Serenity Townhome Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

The Serenity Townhome Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Magnificient 4Bd W/ Pool @ Storey Lake Resort 2648

Vacation Home

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Osceola
Magnificient 4Bd W/ Pool @ Storey Lake Resort 2648 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 7.2 mi (11.7 km) from Disney Springs™ and 8.3 mi (13.3 km) from Walt Disney World® Resort.

Magnificient 4Bd W/ Pool @ Storey Lake Resort 2648 Rooms
Make yourself comfortable in your vacation home.

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4.7/5
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Solara Resort 7 Bedroom Private Pool+Spa Movie Room Home 7 Home

Vacation Home

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Osceola
Solara Resort 7 Bedroom Private Pool+Spa Movie Room Home 7 Home Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This golf vacation home is 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.1 km) from ESPN Wide World of Sports Complex.

Solara Resort 7 Bedroom Private Pool+Spa Movie Room Home 7 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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6BR Private Pool, Spa, Gameroom, Close to Disney

Vacation Home

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Osceola
6BR Private Pool, Spa, Gameroom, Close to Disney Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 5.8 mi (9.3 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.2 km) from Old Town.

6BR Private Pool, Spa, Gameroom, Close to 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.

6BR Private Pool, Spa, Gameroom, Close to Disney 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

Cozy 4 Bed 3 Bath Pool Hm With Game Room-4450np 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
Cozy 4 Bed 3 Bath Pool Hm With Game Room-4450np 4 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Veranda Palms), you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.8 mi (11 km) from Disney Springs™ and 7.8 mi (12.6 km) from Walt Disney World® Resort.

Cozy 4 Bed 3 Bath Pool Hm With Game Room-4450np 4 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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South-facing Home w/ Private Pool/spa and Resort Lazy River & gym

Vacation Home

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Osceola
South-facing Home w/ Private Pool/spa and Resort Lazy River & gym Location
When you stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.1 mi (17.9 km) from Walt Disney World® Resort and 11.5 mi (18.4 km) from Old Town.

South-facing Home w/ Private Pool/spa and Resort Lazy River & gym Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

South-facing Home w/ Private Pool/spa and Resort Lazy River & gym Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

1533mc -non-renting The Retreat at Championsgate

Vacation Home

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Osceola
1533mc -non-renting 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 Old Town and ChampionsGate Golf Club. This golf vacation home is 11.9 mi (19.1 km) from ESPN Wide World of Sports Complex and 12 mi (19.2 km) from Walt Disney World® Resort.

1533mc -non-renting The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1533mc -non-renting The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Room

Wilmington Grand Escape

Vacation Home

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Osceola
Wilmington Grand Escape Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly 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.

Wilmington Grand Escape Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional features at this vacation home include an arcade/game room and gas grills.

Wilmington Grand Escape Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

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Exterior & Views

2735book

Vacation Home

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Osceola
2735book 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 spa 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.

2735book Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

2735book Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Sport & Beauty

284 Encore at Reunion

Vacation Home

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Osceola
284 Encore at Reunion Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This golf vacation home is 5.7 mi (9.1 km) from Walt Disney World® Resort and 7.9 mi (12.7 km) from ESPN Wide World of Sports Complex.

284 Encore at Reunion Rooms
Make yourself comfortable in this vacation home, which features a private pool and a Smart TV. Wireless internet access (surcharge) is available to keep you connected.

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Others

Private Pool Townhouse Near Disney Parks - Family Friendly

Vacation Home

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Osceola
Private Pool Townhouse Near Disney Parks - Family Friendly 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 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Private Pool Townhouse Near Disney Parks - Family Friendly Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Private Pool Townhouse Near Disney Parks - Family Friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Family-friendly Townhouse w/ Private Pool & Clubhouse

Vacation Home

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Osceola
Family-friendly Townhouse w/ Private Pool & Clubhouse 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.

Family-friendly Townhouse w/ Private Pool & Clubhouse Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Family-friendly Townhouse w/ Private Pool & Clubhouse Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Ohana Haven 5 Bedroom Home

Vacation Home

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Osceola
Ohana Haven 5 Bedroom Home Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 6.1 mi (9.9 km) from ESPN Wide World of Sports Complex and 6.4 mi (10.3 km) from Old Town.

Ohana Haven 5 Bedroom Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Windsor Hills by Nova

Vacation Home

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Osceola
Windsor Hills by Nova Location
Located in Kissimmee (Windsor Hills), Windsor Hills by Nova is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 6.1 mi (9.8 km) from Disney's Hollywood Studios® and 7.8 mi (12.5 km) from Disney Springs™.

Windsor Hills by Nova Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as an outdoor pool or a waterslide.

Windsor Hills by Nova Rooms
Make yourself at home in one of the 26 air-conditioned rooms featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private furnished lanais. Flat-screen televisions and video-game consoles are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include microwaves and coffee/tea makers, as well as phones with free local calls.

Important Information
This property is closed from June 6 2025 to June 5 2027 (dates subject to change).

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3.0/5
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Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts

Vacation Home

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Osceola
Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts 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 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®.

Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, an outdoor tennis court, and a sauna. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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3 Bedroom,3 Bath Townhouse in Gate Resort 3 Townhouse by RedAwning

Vacation Home

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Osceola
3 Bedroom,3 Bath Townhouse in Gate Resort 3 Townhouse by RedAwning 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 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 8.2 mi (13.2 km) from Disney's Hollywood Studios®.

3 Bedroom,3 Bath Townhouse in Gate Resort 3 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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Room

Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat

Vacation Home

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Osceola
Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat 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 Old Town. This vacation home is 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.4 km) from Disney's Hollywood Studios®.

Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat Facility and Service
Take advantage of recreation opportunities such as a sauna, or other amenities including complimentary wireless internet access and an arcade/game room.

Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Vacation Homes in Osceola

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