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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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Ip62813 - Encantada Resort - 2 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ip62813 - Encantada Resort - 2 Bed 2.5 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 7.1 mi (11.5 km) from Disney's Animal Kingdom® Theme Park and 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex.

Ip62813 - Encantada Resort - 2 Bed 2.5 Baths Townhome 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.

Ip62813 - Encantada Resort - 2 Bed 2.5 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private hot tub 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.

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Sport & Beauty

West Lucaya Resort by FunQuest Vacation

Vacation Home

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Osceola
West Lucaya Resort by FunQuest Vacation Location
With a stay at West Lucaya Resort by FunQuest Vacation in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.4 mi (12 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.4 km) from ESPN Wide World of Sports Complex.

West Lucaya Resort by FunQuest Vacation Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and barbecue grills.

West Lucaya Resort by FunQuest Vacation Rooms
Make yourself at home in one of the 10 air-conditioned rooms featuring kitchens with refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and coffee/tea makers.

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3.8/5
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Exterior & Views

3BR Lake Berkley Pool Home Near Disney

Vacation Home

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Osceola
3BR Lake Berkley Pool Home Near Disney Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 8.9 mi (14.4 km) from Disney Springs™ and 9.1 mi (14.6 km) from Walt Disney World® Resort.

3BR Lake Berkley Pool Home Near Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden.

3BR Lake Berkley Pool Home Near Disney Rooms
Make yourself comfortable in this villa, which features a private pool and a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a washer/dryer, and a crib/infant bed (complimentary) can be requested.

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House 12Q With Pool With Heating - and Game Room

Vacation Home

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Osceola
House 12Q With Pool With Heating - and Game Room Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 9 mi (14.4 km) from Disney Springs™ and 9.9 mi (16 km) from Walt Disney World® Resort.

House 12Q With Pool With Heating - and Game Room Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

House 12Q With Pool With Heating - and Game Room Rooms
Your villa features a Smart TV. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a separate sitting area and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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Exterior & Views

18 Guest Resort Home - Near Disney

Vacation Home

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Osceola
18 Guest Resort Home - Near Disney 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 9.6 mi (15.4 km) from Disney Springs™ and 10.6 mi (17.1 km) from Walt Disney World® Resort.

18 Guest Resort Home - Near Disney Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and gas grills.

18 Guest Resort Home - Near Disney Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A 32-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected.

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4.0/5
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Exterior & Views

Beachy Retreat

Vacation Home

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Osceola
Beachy Retreat Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, a 4-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This vacation home is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.5 km) from Disney's Animal Kingdom® Theme Park.

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

Beachy Retreat Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. Digital television is provided for your entertainment. Conveniences include a separate sitting area and a microwave.

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4.0/5
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Others

Beautiful 7 Bed Pool Home With Game Room-9117ecl 7 Bedroom Home

Vacation Home

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Osceola
Beautiful 7 Bed Pool Home With Game Room-9117ecl 7 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 11.8 mi (18.9 km) from Old Town and 12.6 mi (20.2 km) from ESPN Wide World of Sports Complex.

Beautiful 7 Bed Pool Home With Game Room-9117ecl 7 Bedroom Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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5BR Bear's Den Theater, Pool & Spa

Vacation Home

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Osceola
5BR Bear's Den Theater, Pool & Spa Location
Located in Kissimmee (Reunion), this vacation home is within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 7.2 mi (11.6 km) from Walt Disney World® Resort and 9.2 mi (14.8 km) from Old Town.

5BR Bear's Den Theater, Pool & Spa 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.

5BR Bear's Den Theater, Pool & Spa Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fantastic 4 Bd W/ Pool @ Storey Lake Resort 2709

Vacation Home

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Osceola
Fantastic 4 Bd W/ Pool @ Storey Lake Resort 2709 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.

Fantastic 4 Bd W/ Pool @ Storey Lake Resort 2709 Rooms
Make yourself comfortable in your vacation home.

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5.0/5
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Beautiful 6bd Pool Gm Spa Hm Champions Gate-1660mv 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Beautiful 6bd Pool Gm Spa Hm Champions Gate-1660mv 6 Bedroom Home by RedAwning 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 11.4 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

Beautiful 6bd Pool Gm Spa Hm Champions Gate-1660mv 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. 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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Sport & Beauty

6BR Windsor Palms Home by FS FL VH-8036

Vacation Home

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Osceola
6BR Windsor Palms Home by FS FL VH-8036 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 8.2 mi (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.8 km) from Disney's Animal Kingdom® Theme Park.

6BR Windsor Palms Home by FS FL VH-8036 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including an arcade/game room and a picnic area.

6BR Windsor Palms Home by FS FL VH-8036 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and an LCD TV. Your pillowtop bed comes with a down comforter. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a microwave. Cable programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Sunny Home With Themed Rooms in Encore

Vacation Home

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Osceola
Sunny Home With Themed Rooms in 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.

Sunny Home With Themed Rooms in Encore Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Sunny Home With Themed Rooms in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Stunning 4Bd W/ Pool @ Storey Lake 5019

Vacation Home

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Osceola
Stunning 4Bd W/ Pool @ Storey Lake 5019 Location
With a stay at this vacation home in Kissimmee, you'll be a 4-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 km) from Walt Disney World® Resort.

Stunning 4Bd W/ Pool @ Storey Lake 5019 Facility and Service
Take in the views from a garden.

Stunning 4Bd W/ Pool @ Storey Lake 5019 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Satellite television is provided for your entertainment. Conveniences include a desk and a microwave.

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5.0/5
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Bedroom

Windsor at Westside IHR 3100

Vacation Home

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Osceola
Windsor at Westside IHR 3100 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®.

Windsor at Westside IHR 3100 Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Windsor at Westside IHR 3100 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private furnished balcony/patio. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected.

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Bedroom

1517fd-the Retreat at Championsgate

Vacation Home

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Osceola
1517fd-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 (19.2 km) from ESPN Wide World of Sports Complex.

1517fd-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

1517fd-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Dazzling Home With Putting Green at Encore

Vacation Home

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Osceola
Dazzling Home With Putting Green 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 family-friendly vacation home is 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.7 mi (12.3 km) from ESPN Wide World of Sports Complex.

Dazzling Home With Putting Green at Encore Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Dazzling Home With Putting Green at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Ip60304 - Fiesta Key - 3 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ip60304 - Fiesta Key - 3 Bed 2.5 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 10 mi (16 km) from Disney Springs™ and 10.1 mi (16.3 km) from Walt Disney World® Resort.

Ip60304 - Fiesta Key - 3 Bed 2.5 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as an outdoor pool and an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60304 - Fiesta Key - 3 Bed 2.5 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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Bedroom

C1555fd-the Retreat at Championsgate

Vacation Home

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Osceola
C1555fd-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 (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

C1555fd-the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

C1555fd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Fully Booked
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Sport & Beauty

Fd57636 - Lucaya Village - 3 Bed 2 Baths Townhouse

Vacation Home

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Osceola
Fd57636 - Lucaya Village - 3 Bed 2 Baths Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This golf vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex.

Fd57636 - Lucaya Village - 3 Bed 2 Baths Townhouse 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 hot tub or an outdoor tennis court. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Fd57636 - Lucaya Village - 3 Bed 2 Baths Townhouse 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 is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

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​Near Theme Parks! 4 BR's, Sleeps 10! Gorgeous Home, Pool, Patio!

Vacation Home

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Osceola
​Near Theme Parks! 4 BR's, Sleeps 10! Gorgeous Home, Pool, Patio! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This golf 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.

​Near Theme Parks! 4 BR's, Sleeps 10! Gorgeous Home, Pool, Patio! 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 a picnic area and barbecue grills.

​Near Theme Parks! 4 BR's, Sleeps 10! Gorgeous Home, Pool, Patio! Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. There's a private balcony. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. The bathroom has a deep soaking tub.

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1.0/5
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Vacation Homes in Osceola

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