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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
Exterior & Views

Amazing Story Lake Town Home With Pool 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Amazing Story Lake Town Home With Pool 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 6 mi (9.6 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

Amazing Story Lake Town Home With Pool 4 Bedroom Townhouse 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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Spacious Resort Home for Large Groups Near Disney

Vacation Home

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Osceola
Spacious Resort Home for Large Groups Near Disney 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 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Spacious Resort Home for Large Groups Near Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Resort Home for Large Groups Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Fl Special!! Daisy's Den 5 Bedroom Villa by RedAwning

Vacation Home

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Osceola
Fl Special!! Daisy's Den 5 Bedroom Villa by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7 mi (11.3 km) from Old Town and 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex.

Fl Special!! Daisy's Den 5 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Rolling Hills 7900

Vacation Home

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Osceola
Rolling Hills 7900 Location
With a stay at this vacation home in Kissimmee, 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 mi (9.6 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.2 km) from Old Town.

Rolling Hills 7900 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Rolling Hills 7900 Rooms
Make yourself comfortable in your air-conditioned vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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Casita mi Encanto a Cozy & Spacious House, 4-bedroom 3-Bath & pool

Vacation Home

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Osceola
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Others

Gorgeous 4bd Th Pool Windsor At Westside-2018ww 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
Gorgeous 4bd Th Pool Windsor At Westside-2018ww 4 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

Gorgeous 4bd Th Pool Windsor At Westside-2018ww 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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Royal Laguna Villas By Magical Memories

Vacation Home

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Osceola
Royal Laguna Villas By Magical Memories Location
Located in Kissimmee, Royal Laguna Villas By Magical Memories is in the suburbs, within a 10-minute drive of Lake Buena Vista Factory Stores and Fun Spot America. This vacation home is 4.3 mi (7 km) from Old Town and 6.6 mi (10.5 km) from Orlando Vineland Premium Outlets.

Royal Laguna Villas By Magical Memories Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and tour/ticket assistance.

Royal Laguna Villas By Magical Memories Rooms
Make yourself at home in one of the 130 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include microwaves and coffee/tea makers.

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3.3/5(100 Reviews)
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Chic Home With Gaming Loft at Encore

Vacation Home

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Osceola
Chic Home With Gaming Loft at Encore Location
With a stay at this vacation home in Kissimmee (Historic Downtown Kissimmee), you'll be within a 5-minute walk of Kissimmee Lakefront Park and Lake Tohopekaliga. This vacation home is 9.7 mi (15.6 km) from Old Town and 11.6 mi (18.7 km) from Orlando Vineland Premium Outlets.

Chic Home With Gaming Loft at Encore Facility and Service
Enjoy the recreation opportunities such as a hot tub or make use of other amenities including complimentary wireless internet access.

Chic Home With Gaming Loft at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Lovely 7 Bed Pool Home With Game Room-8510phd 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
Lovely 7 Bed Pool Home With Game Room-8510phd 7 Bedroom Home 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 7.2 mi (11.5 km) from ESPN Wide World of Sports Complex and 7.6 mi (12.3 km) from Disney's Hollywood Studios®.

Lovely 7 Bed Pool Home With Game Room-8510phd 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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The Retreat at Champions Gate by Nova

Vacation Home

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Osceola
The Retreat at Champions Gate by Nova Location
With a stay at The Retreat at Champions Gate by Nova in Four Corners, you'll be 3.5 mi (5.7 km) from ChampionsGate Golf Club and 9.3 mi (15 km) from Mystic Dunes Golf Club. This vacation home is 13.3 mi (21.4 km) from Walt Disney World® Resort and 13.5 mi (21.7 km) from ESPN Wide World of Sports Complex.

The Retreat at Champions Gate by Nova Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a sauna, and a fitness center. Additional features at this vacation home include an arcade/game room and barbecue grills.

The Retreat at Champions Gate by Nova Rooms
Make yourself at home in one of the 28 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private patios. Complimentary wireless internet access keeps you connected, and flat-screen televisions are provided for your entertainment. Conveniences include microwaves and coffee/tea makers.

Restaurant and Cafe
Quench your thirst with your favorite drink at the bar/lounge.

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3.2/5
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Exterior & Views

4804crusoe 4 Bedroom Townhouse

Vacation Home

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Osceola
4804crusoe 4 Bedroom Townhouse 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 5.7 mi (9.1 km) from Disney Springs™ and 6.7 mi (10.7 km) from Walt Disney World® Resort.

4804crusoe 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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Exterior & Views

1588sw-the Retreat at Championsgate

Vacation Home

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Osceola
1588sw-the Retreat at Championsgate Location
With a stay at this condo in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf condo is 11.5 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

1588sw-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

1588sw-the Retreat at Championsgate Rooms
Make yourself comfortable in your condo.

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Room

Sophisticated 6BR at Storey Lake Sl2766

Vacation Home

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Osceola
Sophisticated 6BR at Storey Lake Sl2766 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 6.7 mi (10.7 km) from Disney Springs™ and 7.7 mi (12.3 km) from Walt Disney World® Resort.

Sophisticated 6BR at Storey Lake Sl2766 Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Sophisticated 6BR at Storey Lake Sl2766 Rooms
Make yourself comfortable in your vacation home. Conveniences include a desk and an electric kettle.

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5.0/5
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Sport & Beauty

Contemporary 5 Bed 5 Bath Single Family With Upgrades

Vacation Home

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Osceola
Contemporary 5 Bed 5 Bath Single Family With Upgrades Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This vacation home is 6.2 mi (9.9 km) from Walt Disney World® Resort and 7.8 mi (12.6 km) from Disney's Animal Kingdom® Theme Park.

Contemporary 5 Bed 5 Bath Single Family With Upgrades Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Contemporary 5 Bed 5 Bath Single Family With Upgrades Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker, and you can also request a crib/infant bed (surcharge).

Important Information
This property is closed from December 30 2024 to December 29 2026 (dates subject to change).

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4.0/5
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Exterior & Views

6BR Pool Home Windsor Palms by SHV-2238

Private Vacation Home

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Osceola
6BR Pool Home Windsor Palms by SHV-2238 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 (13.3 km) from Disney's Hollywood Studios® and 9.3 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

6BR Pool Home Windsor Palms by SHV-2238 Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access.

6BR Pool Home Windsor Palms by SHV-2238 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private furnished patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Others

1433rf- The Retreat at Championsgate

Vacation Home

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Osceola
1433rf- The Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This golf vacation home is 12.8 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

1433rf- The Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1433rf- The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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8973ccd - The Retreat At Championsgate 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
8973ccd - The Retreat At Championsgate 4 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Four Corners FC. This vacation home is 12.4 mi (20 km) from Old Town and 13.2 mi (21.2 km) from ESPN Wide World of Sports Complex.

8973ccd - The Retreat At Championsgate 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. 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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Exterior & Views

5 Bedrooms S / Solara Home by RedAwning

Vacation Home

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Osceola
5 Bedrooms S / Solara Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

5 Bedrooms S / Solara 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.

5 Bedrooms S / Solara 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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Room

Le Reve 4 Bedroom Vacation Home 4451

Vacation Home

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Osceola
Le Reve 4 Bedroom Vacation Home 4451 Location
Located in Kissimmee, Le Reve 4 Bedroom Vacation Home 4451 is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This hotel is 8.2 mi (13.3 km) from Disney Springs™ and 9.2 mi (14.8 km) from Walt Disney World® Resort.

Le Reve 4 Bedroom Vacation Home 4451 Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Le Reve 4 Bedroom Vacation Home 4451 Rooms
Make yourself at home in one of the air-conditioned rooms featuring private pools. Rooms have private balconies. Kitchens are outfitted with refrigerators, ovens, and stovetops. Conveniences include microwaves and coffee/tea makers.

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Sport & Beauty

Paradise Palms Resort by DWS Vacation Villas

Vacation Home

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Osceola
Paradise Palms Resort by DWS Vacation Villas Location
With a stay at Paradise Palms Resort by DWS Vacation Villas in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This family-friendly vacation home is 6.5 mi (10.4 km) from Walt Disney World® Resort and 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park.

Paradise Palms Resort by DWS Vacation Villas Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access, babysitting (surcharge), and an arcade/game room.

Paradise Palms Resort by DWS Vacation Villas Rooms
Treat yourself to a stay in one of the 5 individually decorated guestrooms, featuring private pools and flat-screen televisions. Rooms have private patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include microwaves and coffee/tea makers.

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4.3/5
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Vacation Homes in Osceola

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