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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola

Rolling Hills 7900

Vacation Home

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Osceola
Rolling Hills 7900 Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 6 mi (9.6 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.2 km) from Old Town.

Rolling Hills 7900 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Rolling Hills 7900 Rooms
Make yourself comfortable in your air-conditioned vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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Sport & Beauty

Contemporary 5 Bed 5 Bath Single Family With Upgrades

Vacation Home

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Osceola
Contemporary 5 Bed 5 Bath Single Family With Upgrades 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 6.2 mi (9.9 km) from Walt Disney World® Resort and 7.8 mi (12.6 km) from Disney's Animal Kingdom® Theme Park.

Contemporary 5 Bed 5 Bath Single Family With Upgrades Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Contemporary 5 Bed 5 Bath Single Family With Upgrades Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker, and you can also request a crib/infant bed (surcharge).

Important Information
This property is closed from December 30 2024 to December 29 2026 (dates subject to change).

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4.0/5
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Others

Villa Kohler - Terra Verde Resort

Vacation Home

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Osceola
Villa Kohler - Terra Verde Resort 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 8.8 mi (14.2 km) from Disney Springs™ and 9.1 mi (14.7 km) from Walt Disney World® Resort.

Villa Kohler - Terra Verde Resort Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Villa Kohler - Terra Verde Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker, and housekeeping is provided once per stay.

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Chic Home With Gaming Loft at Encore

Vacation Home

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Osceola
Chic Home With Gaming Loft at Encore Location
With a stay at this vacation home in Kissimmee (Historic Downtown Kissimmee), you'll be within a 5-minute walk of Kissimmee Lakefront Park and Lake Tohopekaliga. This vacation home is 9.7 mi (15.6 km) from Old Town and 11.6 mi (18.7 km) from Orlando Vineland Premium Outlets.

Chic Home With Gaming Loft at Encore Facility and Service
Enjoy the recreation opportunities such as a hot tub or make use of other amenities including complimentary wireless internet access.

Chic Home With Gaming Loft at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Magical Family Home 8min-disneyworld Pool/spa Sleeps 22 Stl103

Vacation Home

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Osceola
Magical Family Home 8min-disneyworld Pool/spa Sleeps 22 Stl103 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.2 mi (9.9 km) from Disney Springs™ and 7.2 mi (11.6 km) from Walt Disney World® Resort.

Magical Family Home 8min-disneyworld Pool/spa Sleeps 22 Stl103 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Magical Family Home 8min-disneyworld Pool/spa Sleeps 22 Stl103 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Aco256584 - Storey Lake Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Aco256584 - Storey Lake Resort - 4 Bed 3 Baths Townhome 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 family-friendly vacation home is 5.7 mi (9.1 km) from Disney Springs™ and 6.7 mi (10.7 km) from Walt Disney World® Resort.

Aco256584 - Storey Lake Resort - 4 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 lazy river. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Aco256584 - Storey Lake Resort - 4 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 or patio. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a sofa bed.

Restaurant and Cafe
You can enjoy a meal at the restaurant serving the guests of this vacation home, 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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Sport & Beauty

Je63369 - The Encore Club Resort - 8 Bed 7 Baths Resort Home

Vacation Home

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Osceola
Je63369 - The Encore Club Resort - 8 Bed 7 Baths Resort Home 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 family-friendly 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®.

Je63369 - The Encore Club Resort - 8 Bed 7 Baths Resort Home Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Je63369 - The Encore Club Resort - 8 Bed 7 Baths Resort Home 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. Quench your thirst with your favorite drink at the bar/lounge.

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Exterior & Views

Villas at Seven Dwarf by FunQuest

Vacation Home

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Osceola
Villas at Seven Dwarf by FunQuest 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 (9.8 km) from Disney Springs™ and 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex.

Villas at Seven Dwarf by FunQuest Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, supervised childcare, and a picnic area.

Villas at Seven Dwarf by FunQuest Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and an electric kettle, and housekeeping is provided on a limited basis.

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Business Facilities

Huge Home With Game Room & Theater Near Disney 1429

Vacation Home

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Osceola
Huge Home With Game Room & Theater Near Disney 1429 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 (20.2 km) from ESPN Wide World of Sports Complex.

Huge Home With Game Room & Theater Near Disney 1429 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.

Huge Home With Game Room & Theater Near Disney 1429 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private patio. A 42-inch flat-screen television is provided, with digital programming available. Conveniences include a microwave and a coffee/tea maker.

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Sport & Beauty

Fv88041 - Storey Lake Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Fv88041 - Storey Lake Resort - 4 Bed 3 Baths Townhome Location
With a stay at this vacation home in Kissimmee (Historic Downtown Kissimmee), you'll be within a 5-minute walk of Kissimmee Lakefront Park and Lake Tohopekaliga. This family-friendly vacation home is 9.7 mi (15.6 km) from Old Town and 11.6 mi (18.7 km) from Orlando Vineland Premium Outlets.

Fv88041 - Storey Lake Resort - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and a lazy river. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Fv88041 - Storey Lake Resort - 4 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 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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Exterior & Views

6BR Pool Home Windsor Palms by SHV-2238

Private Vacation Home

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Osceola
6BR Pool Home Windsor Palms by SHV-2238 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 (13.3 km) from Disney's Hollywood Studios® and 9.3 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

6BR Pool Home Windsor Palms by SHV-2238 Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access.

6BR Pool Home Windsor Palms by SHV-2238 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. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Others

8973ccd - The Retreat At Championsgate 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
8973ccd - The Retreat At Championsgate 4 Bedroom Townhouse 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 Four Corners FC. This vacation home is 12.4 mi (20 km) from Old Town and 13.2 mi (21.2 km) from ESPN Wide World of Sports Complex.

8973ccd - The Retreat At Championsgate 4 Bedroom Townhouse 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

1588sw-the Retreat at Championsgate

Vacation Home

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Osceola
1588sw-the Retreat at Championsgate Location
With a stay at this condo in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf condo is 11.5 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

1588sw-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

1588sw-the Retreat at Championsgate Rooms
Make yourself comfortable in your condo.

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Exterior & Views

4804crusoe 4 Bedroom Townhouse

Vacation Home

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Osceola
4804crusoe 4 Bedroom Townhouse 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 5.7 mi (9.1 km) from Disney Springs™ and 6.7 mi (10.7 km) from Walt Disney World® Resort.

4804crusoe 4 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

1433rf- The Retreat at Championsgate

Vacation Home

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Osceola
1433rf- The Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This golf vacation home is 12.8 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

1433rf- The Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1433rf- The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Bedroom

Fiesta Key 3 Bedroom Vacation Home 4774

Vacation Home

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Osceola
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Sport & Beauty

Paradise Palms Resort by DWS Vacation Villas

Vacation Home

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Osceola
Paradise Palms Resort by DWS Vacation Villas Location
With a stay at Paradise Palms Resort by DWS Vacation Villas in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This family-friendly vacation home is 6.5 mi (10.4 km) from Walt Disney World® Resort and 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park.

Paradise Palms Resort by DWS Vacation Villas Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access, babysitting (surcharge), and an arcade/game room.

Paradise Palms Resort by DWS Vacation Villas Rooms
Treat yourself to a stay in one of the 5 individually decorated guestrooms, featuring private pools and flat-screen televisions. Rooms have private patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include microwaves and coffee/tea makers.

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4.3/5
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Sport & Beauty

The Bliss at Solara

Private Vacation Home

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Osceola
The Bliss at Solara Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This golf vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.5 mi (18.5 km) from Old Town.

The Bliss at Solara Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

The Bliss at Solara Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Bedroom

8932adriatico

Vacation Home

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Osceola
8932adriatico Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

8932adriatico Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

8932adriatico Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a private pool. A kitchen is outfitted with a refrigerator and a microwave. An LCD television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a sofa bed and a washer/dryer.

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Beautiful Home With Private Pool, Game Room and Basketball Court

Vacation Home

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Osceola
Beautiful Home With Private Pool, Game Room and Basketball Court Location
With a stay at this vacation home in Kissimmee (Crescent Lakes), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11.8 mi (18.9 km) from Old Town and 14 mi (22.5 km) from Orlando Vineland Premium Outlets.

Beautiful Home With Private Pool, Game Room and Basketball Court Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an outdoor tennis court. This vacation home also features complimentary wireless internet access and an arcade/game room.

Beautiful Home With Private Pool, Game Room and Basketball Court Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Vacation Homes in Osceola

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