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Vacation Homes in Osceola

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

4BR Townhome Paradise Palms by SHV-8978

Private Vacation Home

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Osceola
4BR Townhome Paradise Palms by SHV-8978 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 9.9 mi (15.9 km) from Disney's Hollywood Studios®.

4BR Townhome Paradise Palms by SHV-8978 Rooms
Make yourself comfortable in this vacation home, which features a private pool and a flat-screen TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Solara Resort 5 Bedroom Townhome Private Pool 5 Home

Vacation Home

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Osceola
Solara Resort 5 Bedroom Townhome Private Pool 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 10.1 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 5 Bedroom Townhome Private Pool 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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Others

Luxury Getaway: Pool, Spa, Games, Theater

Vacation Home

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Osceola
Luxury Getaway: Pool, Spa, Games, Theater 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 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Luxury Getaway: Pool, Spa, Games, Theater 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.

Luxury Getaway: Pool, Spa, Games, Theater Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private balcony or 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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Others

Shake Shack Heated Pool & Hot Tub

Vacation Home

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Osceola
Shake Shack Heated Pool & Hot Tub Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 5.8 mi (9.3 km) from Old Town and 6.4 mi (10.3 km) from ESPN Wide World of Sports Complex.

Shake Shack Heated Pool & Hot Tub Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Shake Shack Heated Pool & Hot Tub 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 kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 42-inch flat-screen television is provided, with digital programming available.

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5.0/5
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Magical Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Magical 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 golf vacation home is 6.8 mi (10.9 km) from Walt Disney World® Resort and 8.8 mi (14.1 km) from Old Town.

Magical 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.

Magical 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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Paradise Falls - Stay for 13

Vacation Home

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Osceola
Paradise Falls - Stay for 13 Location
With a stay at this vacation home in Kissimmee (Veranda Palms), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This luxury vacation home is 7 mi (11.3 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Paradise Falls - Stay for 13 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Paradise Falls - Stay for 13 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 lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 65-inch flat-screen television is provided, with digital programming available.

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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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Sport & Beauty

Grhcup8946 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhcup8946 - Paradise Palms Resort - 4 Bed 3 Baths 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 family-friendly vacation home is 8 mi (12.9 km) from Disney's Animal Kingdom® Theme Park and 8.9 mi (14.4 km) from ESPN Wide World of Sports Complex.

Grhcup8946 - 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.

Grhcup8946 - 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
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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South Facing Pool & Spa - Emerald Island Gated Resort

Vacation Home

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Osceola
South Facing Pool & Spa - Emerald Island Gated Resort Location
When you stay at this vacation home in Kissimmee, you'll be near the airport, within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 7.5 mi (12.1 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

South Facing Pool & Spa - Emerald Island Gated Resort Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a fitness center. This vacation home also features an arcade/game room and barbecue grills.

South Facing Pool & Spa - Emerald Island Gated Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and an outdoor private hot tub. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 55-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave, as well as a phone with free local calls.

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Sport & Beauty

Striking 5br Resort Home Private Pool/spa Disney

Vacation Home

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Osceola
Striking 5br Resort Home Private Pool/spa Disney 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 Mystic Dunes Golf Club. This vacation home is 5.8 mi (9.4 km) from ESPN Wide World of Sports Complex and 6 mi (9.6 km) from Old Town.

Striking 5br Resort Home Private Pool/spa Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Striking 5br Resort Home Private Pool/spa 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.

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Sport & Beauty

Grhmvd1593 - Champions Gate Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhmvd1593 - Champions Gate Resort - 4 Bed 3 Baths Townhouse 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Grhmvd1593 - Champions Gate Resort - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1593 - Champions Gate 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 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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Sport & Beauty

4/3 Paradise Palms Vacation Resort, Private Pool, Near Famous Attractions!!

Vacation Home

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Osceola
4/3 Paradise Palms Vacation Resort, Private Pool, Near Famous Attractions!! 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 6.1 mi (9.9 km) from Walt Disney World® Resort and 7.9 mi (12.8 km) from Disney's Animal Kingdom® Theme Park.

4/3 Paradise Palms Vacation Resort, Private Pool, Near Famous Attractions!! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

4/3 Paradise Palms Vacation Resort, Private Pool, Near Famous Attractions!! Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected. Conveniences include a phone and a refrigerator.

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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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Sport & Beauty

Townhome W/splashpool In Paradise Palms-3201pp 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Townhome W/splashpool In Paradise Palms-3201pp 4 Bedroom Townhouse by RedAwning 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 6.5 mi (10.5 km) from Walt Disney World® Resort and 8.2 mi (13.2 km) from Disney's Animal Kingdom® Theme Park.

Townhome W/splashpool In Paradise Palms-3201pp 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Complimentary wireless internet access is available to keep you connected. Conveniences include a refrigerator and a coffee/tea maker.

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2.0/5
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Others

3 Br 2 Miles To Disney, Pool, Free Wifi And More 3 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
3 Br 2 Miles To Disney, Pool, Free Wifi And More 3 Bedroom Townhouse by RedAwning 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®.

3 Br 2 Miles To Disney, Pool, Free Wifi And More 3 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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Exterior & Views

Luxury Lake View 8 BR Villa With Games Room

Vacation Home

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Osceola
Luxury Lake View 8 BR Villa With Games Room 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 family-friendly 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.

Luxury Lake View 8 BR Villa With Games Room Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You can take advantage of recreational amenities such as an outdoor pool and a fitness center.

Luxury Lake View 8 BR Villa With Games Room Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. There's a private lanai. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a refrigerator and a washer/dryer.

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Orlando Adventure Awaits 4BR Townhouse

Vacation Home

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Osceola
Orlando Adventure Awaits 4BR Townhouse Location
When you stay at this apartment in Kissimmee, you'll be in the entertainment district, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This apartment is 8.5 mi (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Orlando Adventure Awaits 4BR Townhouse Rooms
Make yourself comfortable in your air-conditioned apartment, which features a Smart TV. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include an electric kettle and an all-in-one washing machine and dryer.

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Bathroom

5 Bed 8002

Vacation Home

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Osceola
5 Bed 8002 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 8.1 mi (13 km) from Disney's Hollywood Studios® and 9.1 mi (14.6 km) from Disney's Animal Kingdom® Theme Park.

5 Bed 8002 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

5 Bed 8002 Rooms
Make yourself comfortable in this vacation home, which features a private hot tub and a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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4.0/5
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Others

Relax in Style: Private Pool, Wave Surfing & More!

Vacation Home

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Osceola
Relax in Style: Private Pool, Wave Surfing & More! 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 (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Relax in Style: Private Pool, Wave Surfing & More! Facility and Service
Enjoy recreational amenities such as an outdoor tennis court and a fitness center. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

Relax in Style: Private Pool, Wave Surfing & More! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Storey Lake Resort 6 Bedroom Home Themed Bedrooms 6 Home

Vacation Home

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Osceola
Storey Lake Resort 6 Bedroom Home Themed Bedrooms 6 Home 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 6.1 mi (9.7 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

Storey Lake Resort 6 Bedroom Home Themed Bedrooms 6 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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Vacation Homes in Osceola

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