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Vacation Homes in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
Room

Family Friendly 4Bd PV Pool @ Storey L Resort 4896

Vacation Home

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Osceola
Family Friendly 4Bd PV Pool @ Storey L Resort 4896 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.

Family Friendly 4Bd PV Pool @ Storey L Resort 4896 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and an indoor pool. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Family Friendly 4Bd PV Pool @ Storey L Resort 4896 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 DVD player and cable programming provide entertainment.

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4.6/5
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Exterior & Views

4337 QS - Charming Hideaway

Vacation Home

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Osceola
4337 QS - Charming Hideaway 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 6.9 mi (11.1 km) from Disney Springs™ and 7.6 mi (12.3 km) from Walt Disney World® Resort.

4337 QS - Charming Hideaway Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including barbecue grills.

4337 QS - Charming Hideaway Rooms
Make yourself comfortable in your vacation home. There's a private patio. Satellite television is provided for your entertainment. Conveniences include a desk and an electric kettle.

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Bedroom

Themed 5BR Pool Home in Championsgate Close2disney

Vacation Home

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Osceola
Themed 5BR Pool Home in Championsgate Close2disney Location
Located in Four Corners, this vacation home is within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 12 mi (19.3 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

Themed 5BR Pool Home in Championsgate Close2disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Themed 5BR Pool Home in Championsgate Close2disney 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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4.5/5
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Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560

Vacation Home

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Osceola
Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 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 7.6 mi (12.2 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 Facility and Service
Take in the views from a garden and make use of amenities such as barbecue grills.

Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a full-sized refrigerator/freezer and a stovetop. Conveniences include a desk and a microwave.

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5.0/5
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Room

Amazing House Near the Parks

Vacation Home

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Osceola
Amazing House Near the Parks 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.

Amazing House Near the Parks Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

Amazing House Near the Parks Rooms
Make yourself comfortable in your vacation home.

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Sport & Beauty

Cumbrian Retreat

Vacation Home

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Osceola
Cumbrian Retreat Location
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 10.3 mi (16.5 km) from Disney Springs™ and 10.5 mi (16.8 km) from ESPN Wide World of Sports Complex.

Cumbrian Retreat 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.

Cumbrian Retreat Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a flat-screen TV. There's a private lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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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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Bedroom

Emerald_island_8520

Vacation Home

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Osceola
Emerald_island_8520 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 7.3 mi (11.8 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

Emerald_island_8520 Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Emerald_island_8520 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Wired and wireless internet access is complimentary, and a flat-screen television with satellite programming provides entertainment. The bathroom has a jetted bathtub.

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Fully Booked
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Bedroom

1525fd-the Retreat at Championsgate

Vacation Home

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Osceola
1525fd-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 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

1525fd-the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1525fd-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Exterior & Views

4 Bed 8065

Vacation Home

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Osceola
4 Bed 8065 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 6.3 mi (10.1 km) from ESPN Wide World of Sports Complex and 7 mi (11.2 km) from Disney's Hollywood Studios®.

4 Bed 8065 Facility and Service
This smoke-free vacation home features a playground.

4 Bed 8065 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a stovetop and a dishwasher. There's a private patio. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment. Conveniences include a desk and a washer/dryer.

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Bedroom

1559pw NON Renting 8/15/21the Retreat at Championsgate

Vacation Home

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Osceola
1559pw NON Renting 8/15/21the 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 11.1 mi (17.9 km) from Old Town and 11.9 mi (19.2 km) from ESPN Wide World of Sports Complex.

1559pw NON Renting 8/15/21the Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1559pw NON Renting 8/15/21the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Others

Private Pool Home 3BR 3BA Gated Near Disney 2417

Vacation Home

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Osceola
Private Pool Home 3BR 3BA Gated Near Disney 2417 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 8.3 mi (13.4 km) from Disney's Hollywood Studios®.

Private Pool Home 3BR 3BA Gated Near Disney 2417 Rooms
Make yourself comfortable in your vacation home.

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Condominium House Orlando Florida

Vacation Home

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Osceola
Fully Booked
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Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC

Vacation Home

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Osceola
Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC Location
With a stay at this vacation home in Kissimmee (Trafalgar Village), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11 mi (17.7 km) from Old Town and 13.2 mi (21.3 km) from Orlando Vineland Premium Outlets.

Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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1.0/5
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Exterior & Views

Storey Lake 9BR Wonderland Home 2852

Private Vacation Home

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Osceola
Storey Lake 9BR Wonderland Home 2852 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 7.3 mi (11.7 km) from Walt Disney World® Resort.

Storey Lake 9BR Wonderland Home 2852 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.

Storey Lake 9BR Wonderland Home 2852 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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Solara Resort 5 Bedroom Home with Pool + Game Room 5 Home

Vacation Home

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Osceola
Solara Resort 5 Bedroom Home with Pool + Game Room 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 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.8 km) from ESPN Wide World of Sports Complex.

Solara Resort 5 Bedroom Home with Pool + Game Room 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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Sport & Beauty

1153 KS -luxury Oasis 5br/5ba Home, Private Pool

Vacation Home

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Osceola
1153 KS -luxury Oasis 5br/5ba Home, Private Pool Location
When you stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 12 mi (19.3 km) from Old Town and 12.8 mi (20.5 km) from ESPN Wide World of Sports Complex.

1153 KS -luxury Oasis 5br/5ba Home, Private Pool Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center.

1153 KS -luxury Oasis 5br/5ba Home, Private Pool Rooms
Make yourself comfortable in your vacation home.

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Storey Lake Resort 6br Cozy Home With 2936

Vacation Home

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Osceola
Storey Lake Resort 6br Cozy Home With 2936 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 7.3 mi (11.8 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

Storey Lake Resort 6br Cozy Home With 2936 Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Storey Lake Resort 6br Cozy Home With 2936 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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Interior

Db2633 Windsor Hills Resort Vacation Home

Vacation Home

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Osceola
Db2633 Windsor Hills Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Old Town.

Db2633 Windsor Hills Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Disney Days & Poolside Nights At Storey Lake

Vacation Home

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Osceola
Disney Days & Poolside Nights At Storey Lake 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 5.8 mi (9.3 km) from Disney Springs™ and 6.8 mi (10.9 km) from Walt Disney World® Resort.

Disney Days & Poolside Nights At Storey Lake 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. This vacation home also features gas grills and complimentary use of a nearby fitness facility.

Disney Days & Poolside Nights At Storey Lake Rooms
Treat yourself to a stay in this individually decorated 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, an oven, and a stovetop. Digital television is provided for your entertainment.

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Vacation Homes in Osceola

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