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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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South-facing Home w/ Private Pool/spa and Resort Lazy River & gym

Vacation Home

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Osceola
South-facing Home w/ Private Pool/spa and Resort Lazy River & gym Location
When you stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.1 mi (17.9 km) from Walt Disney World® Resort and 11.5 mi (18.4 km) from Old Town.

South-facing Home w/ Private Pool/spa and Resort Lazy River & gym Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

South-facing Home w/ Private Pool/spa and Resort Lazy River & gym Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

1620mc-the Retreat at Championsgate

Vacation Home

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Osceola
1620mc-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 (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

1620mc-the Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1620mc-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Exterior & Views

Four Bedroom Close to Disney w/ Screened Pool @StoreyLake 4910

Vacation Home

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Osceola
Four Bedroom Close to Disney w/ Screened Pool @StoreyLake 4910 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 6.3 mi (10.1 km) from Walt Disney World® Resort.

Four Bedroom Close to Disney w/ Screened Pool @StoreyLake 4910 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and an indoor pool. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Four Bedroom Close to Disney w/ Screened Pool @StoreyLake 4910 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. 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 flat-screen television with cable programming provides entertainment.

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3.5/5
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Exterior & Views

Formosa Mimosa Margaritaville!

Vacation Home

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Osceola
Formosa Mimosa Margaritaville! 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 6 mi (9.6 km) from Disney's Animal Kingdom® Theme Park and 6.9 mi (11 km) from ESPN Wide World of Sports Complex.

Formosa Mimosa Margaritaville! Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and gas grills.

Formosa Mimosa Margaritaville! 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 balcony/patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 50-inch flat-screen television is provided, with digital programming available.

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5.0/5
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Sport & Beauty

389 Encore at Reunion

Vacation Home

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Osceola
389 Encore at Reunion Location
With a stay at this vacation home, you'll be centrally located in Kissimmee, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This golf 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.

389 Encore at Reunion Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

389 Encore at Reunion Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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4.0/5
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Beautiful Home With Resort Pool and Space for the Whole Family

Vacation Home

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Osceola
Beautiful Home With Resort Pool and Space for the Whole Family Location
When you stay at Beautiful Home With Resort Pool and Space for the Whole Family in Kissimmee, you'll be near the beach, a 3-minute drive from Walt Disney World® Resort and 8 minutes from Old Town.

Beautiful Home With Resort Pool and Space for the Whole Family Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and barbecue grills.

Beautiful Home With Resort Pool and Space for the Whole Family Rooms
The bathroom has a bathtub or shower.

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Room

Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities

Vacation Home

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Osceola
Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities Location
With a stay at this vacation home in Kissimmee (Venetian Bay Villages), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.7 mi (15.6 km) from Disney Springs™ and 10.3 mi (16.6 km) from Walt Disney World® Resort.

Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities Facility and Service
Don't miss out on recreational opportunities including a hot tub and an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor Palms Resort 4 Bedroom Pool Home + Game Room 4 Home

Vacation Home

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Osceola
Windsor Palms Resort 4 Bedroom Pool Home + Game Room 4 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 Mystic Dunes Golf Club. This vacation home is 7 mi (11.3 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.5 km) from Old Town.

Windsor Palms Resort 4 Bedroom Pool Home + Game Room 4 Home Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. 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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Bedroom

1533cpc Solara Resort

Vacation Home

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Osceola
1533cpc Solara Resort 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 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 10.9 mi (17.5 km) from ESPN Wide World of Sports Complex.

1533cpc Solara Resort Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1533cpc Solara Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private furnished balcony/patio. A kitchen is outfitted with a refrigerator 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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Bedroom

Beautiful Townhouse Next to Disney Parks 24

Vacation Home

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Osceola
Beautiful Townhouse Next to Disney Parks 24 Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This cottage is 7.2 mi (11.6 km) from Disney's Animal Kingdom® Theme Park and 8 mi (12.9 km) from ESPN Wide World of Sports Complex.

Beautiful Townhouse Next to Disney Parks 24 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Beautiful Townhouse Next to Disney Parks 24 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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Exterior & Views

4/3 Vacation Home With Private Pool Located at Formosa Gardens!!

Vacation Home

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Osceola
4/3 Vacation Home With Private Pool Located at Formosa Gardens!! Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 6 mi (9.6 km) from Old Town and 6 mi (9.6 km) from ESPN Wide World of Sports Complex.

4/3 Vacation Home With Private Pool Located at Formosa Gardens!! Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

4/3 Vacation Home With Private Pool Located at Formosa Gardens!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Living room

Family Friendly 4 Bedroom close to Disney in Compass Bay Resort 5108

Vacation Home

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Osceola
Family Friendly 4 Bedroom close to Disney in Compass Bay Resort 5108 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 vacation home is 5.4 mi (8.6 km) from Disney Springs™ and 6 mi (9.7 km) from Walt Disney World® Resort.

Family Friendly 4 Bedroom close to Disney in Compass Bay Resort 5108 Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and concierge services. This vacation home also features a television in a common area, charcoal grills, and a vending machine.

Family Friendly 4 Bedroom close to Disney in Compass Bay Resort 5108 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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4.2/5
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Modern Home w/ Private Pool & Spa, Theater, Game Room, and Resort Amenities

Vacation Home

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Osceola
Modern Home w/ Private Pool & Spa, Theater, Game Room, and Resort Amenities 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 11.2 mi (18.1 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

Modern Home w/ Private Pool & Spa, Theater, Game Room, and Resort Amenities Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a sauna, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Modern Home w/ Private Pool & Spa, Theater, Game Room, and Resort Amenities Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Others

Tropical Vibes

Vacation Home

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Osceola
Tropical Vibes Location
With a stay at Tropical Vibes in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 6 mi (9.6 km) from Old Town and 6 mi (9.6 km) from ESPN Wide World of Sports Complex.

Tropical Vibes Rooms
Make yourself at home in one of the individually decorated guestrooms, featuring kitchens with refrigerators and ovens. Rooms have private furnished patios. 42-inch flat-screen televisions are provided, with digital programming available. Conveniences include separate sitting areas and microwaves.

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Deluxe Mansion With Swim up Bar and Pool Slide at Reunion

Vacation Home

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Osceola
Deluxe Mansion With Swim up Bar and Pool Slide at Reunion 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 6.9 mi (11.1 km) from Walt Disney World® Resort and 8.9 mi (14.3 km) from Old Town.

Deluxe Mansion With Swim up Bar and Pool Slide at Reunion Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Deluxe Mansion With Swim up Bar and Pool Slide at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Colorful Home With Pool, Patio, Kitchen, Washer/dryer, & Game Room

Vacation Home

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Osceola
Colorful Home With Pool, Patio, Kitchen, Washer/dryer, & Game Room Location
With a stay at this vacation home in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.1 mi (14.7 km) from Disney Springs™ and 9.6 mi (15.4 km) from Walt Disney World® Resort.

Colorful Home With Pool, Patio, Kitchen, Washer/dryer, & Game Room Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Colorful Home With Pool, Patio, Kitchen, Washer/dryer, & Game Room Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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Exterior & Views

Coconut Cabana: Access 4 Most!

Vacation Home

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Osceola
Coconut Cabana: Access 4 Most! 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 6.1 mi (9.9 km) from Disney's Animal Kingdom® Theme Park and 6.6 mi (10.6 km) from ESPN Wide World of Sports Complex.

Coconut Cabana: Access 4 Most! Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub.

Coconut Cabana: Access 4 Most! 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 balcony/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.

See details
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Sport & Beauty

Cumbrian Retreat 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
Cumbrian Retreat 4 Bedroom Home by RedAwning 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 family-friendly vacation home is 10.3 mi (16.5 km) from Disney Springs™ and 10.5 mi (16.8 km) from ESPN Wide World of Sports Complex.

Cumbrian Retreat 4 Bedroom Home by RedAwning Facility and Service
This smoke-free vacation home offers games and a foosball table.

Cumbrian Retreat 4 Bedroom Home by RedAwning Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop. There's a private patio. Complimentary wireless internet access is available to keep you connected.

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Spa

5BR Reunion Estate Private Pool & Golf Views

Vacation Home

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Osceola
5BR Reunion Estate Private Pool & Golf Views 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 7.1 mi (11.5 km) from Walt Disney World® Resort and 9.2 mi (14.7 km) from Old Town.

5BR Reunion Estate Private Pool & Golf Views Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Reunion Estate Private Pool & Golf Views Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
Fully Booked
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C1529fd-the Retreat at Championsgate

Vacation Home

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Osceola
C1529fd-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 (19.3 km) from ESPN Wide World of Sports Complex.

C1529fd-the Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

C1529fd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

See details
Fully Booked
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Vacation Homes in Osceola

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