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Vacation Homes in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Disney Area 4 Bed Emerald Island 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Disney Area 4 Bed Emerald Island 4 Bedroom Townhouse 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 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex and 7 mi (11.2 km) from Old Town.

Disney Area 4 Bed Emerald Island 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment. Conveniences include a coffee/tea maker and a washing machine.

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Bathroom

Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102

Vacation Home

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Osceola
Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.4 mi (8.7 km) from Disney Springs™ and 6.1 mi (9.8 km) from Walt Disney World® Resort.

Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. 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 Smart television with cable programming provides entertainment.

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4.0/5
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Modern Townhouse With Private Pool, Resort Amenities, Themed Rooms and More

Vacation Home

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Osceola
Modern Townhouse With Private Pool, Resort Amenities, Themed Rooms and More Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 6.2 mi (10.1 km) from Walt Disney World® Resort.

Modern Townhouse With Private Pool, Resort Amenities, Themed Rooms and More 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.

Modern Townhouse With Private Pool, Resort Amenities, Themed Rooms and More Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Private kitchen

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161

Vacation Home

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Osceola
Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161 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 5.8 mi (9.3 km) from ESPN Wide World of Sports Complex.

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. 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 Smart television with cable programming provides entertainment.

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3.8/5
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Windsor Hills 3 Bedroom Private Pool Townhome 3 Townhouse

Vacation Home

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Osceola
Windsor Hills 3 Bedroom Private Pool Townhome 3 Townhouse Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 6 mi (9.6 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.9 km) from Disney's Hollywood Studios®.

Windsor Hills 3 Bedroom Private Pool Townhome 3 Townhouse 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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Beautiful Golf Course View Townhome!

Vacation Home

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Osceola
Beautiful Golf Course View Townhome! Location
With a stay at this vacation home in Four Corners, you'll be near the beach, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.2 mi (19.6 km) from Old Town and 12.6 mi (20.3 km) from Walt Disney World® Resort.

Beautiful Golf Course View Townhome! Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Beautiful Golf Course View Townhome! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Hamlet by I-4 · New! 5 Bedroom Pool Villa. Sleep 15+ Orlando

Vacation Home

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Osceola
Hamlet by I-4 · New! 5 Bedroom Pool Villa. Sleep 15+ Orlando Location
With a stay at this vacation home in Kissimmee (The Hamlets), you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.6 mi (10.6 km) from Disney Springs™ and 7.6 mi (12.2 km) from ESPN Wide World of Sports Complex.

Hamlet by I-4 · New! 5 Bedroom Pool Villa. Sleep 15+ Orlando Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Hamlet by I-4 · New! 5 Bedroom Pool Villa. Sleep 15+ Orlando Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. The vacation home has a memory foam bed.

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Sport & Beauty

Grhcat8968 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhcat8968 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Grhcat8968 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Dip into one of the 2 hot tubs or enjoy other recreational amenities including a complimentary water park and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcat8968 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable programming along with a video-game console are provided for your entertainment.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Wrap up your day with a drink at the poolside bar.

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Aqua Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Aqua Townhouse With Games Room at Reunion 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 6.8 mi (10.9 km) from Walt Disney World® Resort and 8.8 mi (14.1 km) from Old Town.

Aqua Townhouse With Games Room at Reunion Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Aqua Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

7BR Pool Home Emerald Island by SHV-2793

Private Vacation Home

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Osceola
7BR Pool Home Emerald Island by SHV-2793 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 8.1 mi (13 km) from Disney's Hollywood Studios® and 9.1 mi (14.6 km) from Disney's Animal Kingdom® Theme Park.

7BR Pool Home Emerald Island by SHV-2793 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

7BR Pool Home Emerald Island by SHV-2793 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. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Championsgate Resort Vacation Pool & Spa Home With Resort Clubhouse Amenity Access 8 Bedroom Home

Vacation Home

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Osceola
Championsgate Resort Vacation Pool & Spa Home With Resort Clubhouse Amenity Access 8 Bedroom 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 Reunion Resort Golf Course. This vacation home is 11.6 mi (18.7 km) from Old Town and 12.4 mi (20 km) from ESPN Wide World of Sports Complex.

Championsgate Resort Vacation Pool & Spa Home With Resort Clubhouse Amenity Access 8 Bedroom 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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Sport & Beauty

2652 SS - Enchanted 4-bedroom Disney Haven

Vacation Home

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Osceola
2652 SS - Enchanted 4-bedroom Disney Haven Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 5-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This golf vacation home is 5 mi (8.1 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.5 km) from Old Town.

2652 SS - Enchanted 4-bedroom Disney Haven Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center.

2652 SS - Enchanted 4-bedroom Disney Haven Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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5-bedroom House With Pool and spa Near Disney

Vacation Home

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Osceola
5-bedroom House With Pool and spa Near Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This villa is 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

5-bedroom House With Pool and spa Near Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access and barbecue grills.

5-bedroom House With Pool and spa Near Disney Rooms
Make yourself comfortable in this villa, which features a private pool and a Smart TV. There's a private furnished patio. A kitchen is outfitted with a full-sized refrigerator/freezer and a stovetop. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

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Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as a complimentary water park or a hot tub. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable 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. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Extraordinary Solara 7BR Private Pool/spa Near Disney

Vacation Home

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Osceola
Extraordinary Solara 7BR Private Pool/spa Near Disney 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 vacation home is 8.7 mi (14.1 km) from Walt Disney World® Resort and 10.5 mi (17 km) from Disney's Animal Kingdom® Theme Park.

Extraordinary Solara 7BR Private Pool/spa Near Disney Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Extraordinary Solara 7BR Private Pool/spa Near Disney 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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Championsgate 8 bedroom, Game room, Pool, Theater 8 Home

Vacation Home

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Osceola
Championsgate 8 bedroom, Game room, Pool, Theater 8 Home 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 vacation home is 11.8 mi (19.1 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Championsgate 8 bedroom, Game room, Pool, Theater 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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Championsgate Resort 8 Bedroom Pool Home w Theater Room 8 Home

Vacation Home

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Osceola
Championsgate Resort 8 Bedroom Pool Home w Theater Room 8 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 Reunion Resort Golf Course. This vacation home is 11.8 mi (19 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 8 Bedroom Pool Home w Theater Room 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

Dream Vacation Home Close to Disney SL4839

Vacation Home

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Osceola
Dream Vacation Home Close to Disney SL4839 Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 5.6 mi (8.9 km) from Disney Springs™ and 6.6 mi (10.6 km) from Walt Disney World® Resort.

Dream Vacation Home Close to Disney SL4839 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.

Dream Vacation Home Close to Disney SL4839 Rooms
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with a refrigerator and an oven. A flat-screen television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a phone, as well as a microwave and a coffee/tea maker.

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The Tranquil Townhome - Elegant Townhome in Reunion Resort

Vacation Home

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Osceola
The Tranquil Townhome - Elegant Townhome in Reunion Resort Location
Located in Kissimmee (Reunion), The Tranquil Townhome - Elegant Townhome in Reunion Resort is 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 Tranquil Townhome - Elegant Townhome in Reunion Resort Rooms
Make yourself at home in one of the individually decorated guestrooms. Bathrooms with bathtubs or showers are provided.

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Exterior & Views

Ov2066 - Windsor Hills Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov2066 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov2066 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2066 - Windsor Hills Resort - 3 Bed 3 Baths Townhome 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.

See details
Fully Booked
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Vacation Homes in Osceola

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