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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
Others

1516mb- the Retreat at Championsgate

Vacation Home

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Osceola
1516mb- 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 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.4 km) from ESPN Wide World of Sports Complex.

1516mb- the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1516mb- the Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Pool

Chic Resort Getaway 15 Min to Disney

Vacation Home

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Osceola
Chic Resort Getaway 15 Min to Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.1 mi (8.2 km) from Disney Springs™ and 6.1 mi (9.9 km) from Walt Disney World® Resort.

Chic Resort Getaway 15 Min to Disney Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Chic Resort Getaway 15 Min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Modern Magic At Storey Lake - 6BR

Vacation Home

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Osceola
Modern Magic At Storey Lake - 6BR 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 mi (11.2 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Modern Magic At Storey Lake - 6BR Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features a picnic area and gas grills.

Modern Magic At Storey Lake - 6BR Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and an outdoor private hot tub. Conveniences include a separate sitting area and a washer/dryer.

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Others

Ip60392 - Fiesta Key - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ip60392 - Fiesta Key - 3 Bed 3 Baths Townhome 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 golf vacation home is 9.8 mi (15.9 km) from Disney Springs™ and 9.9 mi (15.9 km) from ESPN Wide World of Sports Complex.

Ip60392 - Fiesta Key - 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 an outdoor pool or an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60392 - Fiesta Key - 3 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. A flat-screen television with cable programming is available for your entertainment, and a video-game console is also provided. Conveniences include a microwave and a washer/dryer.

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Family-friendly Townhouse w/ Game Room Near Disney

Vacation Home

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Osceola
Family-friendly Townhouse w/ Game Room Near Disney Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.1 mi (11.5 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.4 km) from Old Town.

Family-friendly Townhouse w/ Game Room Near Disney 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.

Family-friendly Townhouse w/ Game Room 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

4630 4 Bedroom Private Pool Home, Cumbrian Lakes

Vacation Home

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Osceola
4630 4 Bedroom Private Pool Home, Cumbrian Lakes 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 spa vacation home is 10.1 mi (16.3 km) from Disney Springs™ and 10.3 mi (16.5 km) from Walt Disney World® Resort.

4630 4 Bedroom Private Pool Home, Cumbrian Lakes Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

4630 4 Bedroom Private Pool Home, Cumbrian Lakes Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wired and wireless internet access is available.

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Others

Orlando Luxury Home With Pool Heat Included

Private Vacation Home

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Osceola
Orlando Luxury Home With Pool Heat Included Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 5.5 mi (8.8 km) from Walt Disney World® Resort and 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex.

Orlando Luxury Home With Pool Heat Included Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and an outdoor tennis court.

Orlando Luxury Home With Pool Heat Included Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse

Vacation Home

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Osceola
Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse 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 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center.

Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse 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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Enchanted Clock Tower

Private Vacation Home

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Osceola
Enchanted Clock Tower Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 5.6 mi (9 km) from Disney Springs™ and 6.6 mi (10.7 km) from Walt Disney World® Resort.

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

Enchanted Clock Tower Rooms
Make yourself comfortable in your air-conditioned vacation home, featuring a refrigerator and a microwave. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include a coffee/tea maker and a washer/dryer.

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Interior

Fp8208 Windsor Palms Resort Vacation Home

Vacation Home

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Osceola
Fp8208 Windsor Palms Resort Vacation Home Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Disney's Hollywood Studios®.

Fp8208 Windsor Palms 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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Others

Grhcap8875 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhcap8875 - 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 8.2 mi (13.2 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.6 km) from ESPN Wide World of Sports Complex.

Grhcap8875 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcap8875 - 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 television is 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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Charming Oasis With Home Theater at Encore

Vacation Home

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Osceola
Charming Oasis With Home Theater at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This 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.

Charming Oasis With Home Theater at Encore Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

Charming Oasis With Home Theater at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Regal Oaks Resort

Vacation Home

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Osceola
Regal Oaks Resort Location
With a stay at this vacation home in Kissimmee, you'll be a 1-minute drive from Old Town and 8 minutes from Walt Disney World® Resort. This vacation home is 4.3 mi (7 km) from ESPN Wide World of Sports Complex and 4.6 mi (7.4 km) from Disney's Hollywood Studios®.

Regal Oaks Resort Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and charcoal grills.

Regal Oaks Resort Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a Smart TV. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a coffee/tea maker and a ceiling fan.

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5.0/5
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Family & Kids

Disney Getaway: Pool, Spa & Lake Views

Vacation Home

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Osceola
Disney Getaway: Pool, Spa & Lake Views Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Disney Getaway: Pool, Spa & Lake Views 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.

Disney Getaway: Pool, Spa & Lake Views 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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Others

8946ptd- The Retreat At Championsgate 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
8946ptd- The Retreat At Championsgate 6 Bedroom Home 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 Highland Reserve Golf Club. This vacation home is 12.5 mi (20 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

8946ptd- The Retreat At Championsgate 6 Bedroom Home 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

1643 LA - Luxurious Retreat Windsor at Westside

Vacation Home

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Osceola
1643 LA - Luxurious Retreat Windsor at Westside Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This golf vacation home is 9 mi (14.5 km) from Walt Disney World® Resort and 10.7 mi (17.2 km) from Disney's Animal Kingdom® Theme Park.

1643 LA - Luxurious Retreat Windsor at Westside Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center.

1643 LA - Luxurious Retreat Windsor at Westside Rooms
Make yourself comfortable in your vacation home.

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Exterior & Views

9077hs-the Retreat at Championsgate

Vacation Home

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Osceola
9077hs-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 Mystic Dunes Golf Club. This golf vacation home is 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

9077hs-the Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

9077hs-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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

See details
Fully Booked
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Others

Grhmvd1688 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhmvd1688 - Champions Gate Resort - 6 Bed 6 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 11.6 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Grhmvd1688 - Champions Gate Resort - 6 Bed 6 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.

Grhmvd1688 - Champions Gate Resort - 6 Bed 6 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.

See details
Fully Booked
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Others

Allamanda Holiday Home 4 Bedroom

Vacation Home

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Osceola
Allamanda Holiday Home 4 Bedroom Location
With a stay at this vacation home in Kissimmee (Seasons), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 8.5 mi (13.7 km) from Disney Springs™ and 8.7 mi (13.9 km) from ESPN Wide World of Sports Complex.

Allamanda Holiday Home 4 Bedroom Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Allamanda Holiday Home 4 Bedroom Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. A kitchen is outfitted with a refrigerator. Complimentary wireless internet access is available to keep you connected. Conveniences include a separate sitting area and a coffee/tea maker, as well as a phone with free local calls.

See details
4.0/5
Fully Booked
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Others

Grhmvd1638 - Champions Gate Resort - 6 Bed 5 Baths House

Vacation Home

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Osceola
Grhmvd1638 - Champions Gate Resort - 6 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Grhmvd1638 - Champions Gate Resort - 6 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1638 - Champions Gate Resort - 6 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.

See details
Fully Booked
Let's check on other dates!
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Vacation Homes in Osceola

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