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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
Sport & Beauty

Ip60240 - Windsor Palms Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ip60240 - Windsor Palms Resort - 3 Bed 3 Baths Townhome 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 family-friendly vacation home is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.3 mi (11.8 km) from Old Town.

Ip60240 - Windsor Palms Resort - 3 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 outdoor tennis courts. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60240 - Windsor Palms Resort - 3 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.

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Exterior & Views

Stunning 4Bd Sleeps9 w Jacuzzi Close to Disney @ Compass Bay 5113

Private Vacation Home

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Osceola
Stunning 4Bd Sleeps9 w Jacuzzi Close to Disney @ Compass Bay 5113 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 (8.6 km) from Disney Springs™ and 6 mi (9.7 km) from Walt Disney World® Resort.

Stunning 4Bd Sleeps9 w Jacuzzi Close to Disney @ Compass Bay 5113 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Stunning 4Bd Sleeps9 w Jacuzzi Close to Disney @ Compass Bay 5113 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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3.0/5
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Bedroom

Champions Gate IHR 4036

Private Vacation Home

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Osceola
Champions Gate IHR 4036 Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This spa vacation home is 11.5 mi (18.4 km) from Old Town and 12.3 mi (19.9 km) from ESPN Wide World of Sports Complex.

Champions Gate IHR 4036 Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You're sure to appreciate the recreational amenities, including an outdoor pool and a fitness center.

Champions Gate IHR 4036 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Sport & Beauty

Kissimmee Vacation Homes by Shine FM

Vacation Home

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Osceola
Kissimmee Vacation Homes by Shine FM Location
With a stay at Kissimmee Vacation Homes by Shine FM in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This condo is 6.6 mi (10.7 km) from Old Town and 6.8 mi (10.9 km) from ESPN Wide World of Sports Complex.

Kissimmee Vacation Homes by Shine FM Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

Kissimmee Vacation Homes by Shine FM Rooms
Treat yourself to a stay in one of the 4 individually decorated guestrooms, featuring private pools and flat-screen televisions. Kitchens are outfitted with refrigerators, ovens, and stovetops. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include desks and microwaves, and housekeeping is provided once per stay.

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4.1/5
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Family & Kids

1584mc-the Retreat at Championsgate

Vacation Home

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Osceola
1584mc-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.

1584mc-the Retreat at Championsgate Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

1584mc-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Sport & Beauty

Windsor at Westside Homes by Atlas VH

Vacation Home

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Osceola
Windsor at Westside Homes by Atlas VH 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.

Windsor at Westside Homes by Atlas VH Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

Windsor at Westside Homes by Atlas VH Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wired internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Bedroom

Bright House 9159

Private Vacation Home

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Osceola
Bright House 9159 Location
Located in Four Corners, this vacation home is within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 12 mi (19.3 km) from Old Town and 13.4 mi (21.5 km) from Walt Disney World® Resort.

Bright House 9159 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Bright House 9159 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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Living area

Modern Oasis Near Shopping n Golf Course w Pool

Vacation Home

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Osceola
Modern Oasis Near Shopping n Golf Course w Pool Location
With a stay at this vacation home in Four Corners, you'll be near the beach, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12 mi (19.4 km) from Old Town and 12.7 mi (20.4 km) from Walt Disney World® Resort.

Modern Oasis Near Shopping n Golf Course w Pool Facility and Service
Take advantage of recreation opportunities including an outdoor pool and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Modern Oasis Near Shopping n Golf Course w Pool Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Golden Hours at Paradise Palms

Vacation Home

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Osceola
Golden Hours at Paradise Palms 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 Old Town. This golf vacation home is 7.9 mi (12.8 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.7 km) from ESPN Wide World of Sports Complex.

Golden Hours at Paradise Palms Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Golden Hours at Paradise Palms Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private plunge pool. Conveniences include a separate sitting area and a washer/dryer.

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Bedroom

4 Bed 4981

Vacation Home

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Osceola
4 Bed 4981 Location
With a stay at this vacation home in Kissimmee (Trafalgar Village), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11.1 mi (17.8 km) from Old Town and 13.3 mi (21.4 km) from Orlando Vineland Premium Outlets.

4 Bed 4981 Facility and Service
This smoke-free vacation home features a playground.

4 Bed 4981 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private patio. A kitchen is outfitted with a stovetop and a dishwasher. Complimentary wired and wireless internet access is available.

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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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ChampionsGate Resort 10 Bedroom Vacation Home - Includes resort clubhouse amenity access! 10 Home

Vacation Home

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Osceola
ChampionsGate Resort 10 Bedroom Vacation Home - Includes resort clubhouse amenity access! 10 Home Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12 mi (19.3 km) from Old Town and 12.8 mi (20.5 km) from ESPN Wide World of Sports Complex.

ChampionsGate Resort 10 Bedroom Vacation Home - Includes resort clubhouse amenity access! 10 Home 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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Bedroom

Private Screened Splash Pool Overlooking Tranquil Lake Right Beside Disney World by Florida Dream Homes

Vacation Home

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Osceola
Private Screened Splash Pool Overlooking Tranquil Lake Right Beside Disney World by Florida Dream Homes 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 vacation home is 7.1 mi (11.4 km) from Disney's Animal Kingdom® Theme Park and 7.3 mi (11.7 km) from ESPN Wide World of Sports Complex.

Private Screened Splash Pool Overlooking Tranquil Lake Right Beside Disney World by Florida Dream Homes Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

Private Screened Splash Pool Overlooking Tranquil Lake Right Beside Disney World by Florida Dream Homes Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Wired and wireless internet access is complimentary, and a flat-screen television with satellite programming provides entertainment.

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Fully Booked
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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

Elegant Retreat With Private Pool & Spa

Vacation Home

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Osceola
Elegant Retreat With Private Pool & Spa 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 12.3 mi (19.9 km) from Old Town and 13.1 mi (21.1 km) from ESPN Wide World of Sports Complex.

Elegant Retreat With Private Pool & Spa Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Elegant Retreat With Private Pool & Spa 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

Lovely Vacation Townhouse with Private Pool SL3103

Vacation Home

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Osceola
Lovely Vacation Townhouse with Private Pool SL3103 Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 5.9 mi (9.5 km) from Disney Springs™ and 6 mi (9.7 km) from ESPN Wide World of Sports Complex.

Lovely Vacation Townhouse with Private Pool SL3103 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. Additional amenities at this condo include complimentary wireless internet access and an arcade/game room.

Lovely Vacation Townhouse with Private Pool SL3103 Rooms
Make yourself comfortable in this air-conditioned condo, 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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5.0/5
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Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly

Vacation Home

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Osceola
Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Orlando Vineland Premium Outlets and Old Town. This vacation home is 10.1 mi (16.3 km) from Disney Springs™ and 10.6 mi (17.1 km) from Orange County Convention Center.

Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly 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.

Single-story House With Private Pool, Alfresco Dining, & Lanai - Dog-friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
5.0/5
Fully Booked
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6Br Retreat W/ South Pool, Spa & Game Room Fun

Vacation Home

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Osceola
6Br Retreat W/ South Pool, Spa & Game Room Fun 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 family-friendly vacation home is 12 mi (19.3 km) from Old Town and 14.2 mi (22.9 km) from Orlando Vineland Premium Outlets.

6Br Retreat W/ South Pool, Spa & Game Room Fun Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

6Br Retreat W/ South Pool, Spa & Game Room Fun Rooms
Make yourself comfortable in this vacation home, which features a private pool and an outdoor private hot tub. There's a private patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 75-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected.

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3.0/5
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Windsor Hills Resort Vacation Home Ts7718

Vacation Home

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Osceola
Windsor Hills Resort Vacation Home Ts7718 Location
Located in Kissimmee (Windsor Hills), this cottage is within a 10-minute drive of Walt Disney World® Resort and Old Town. This cottage is 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.9 km) from Disney's Hollywood Studios®.

Windsor Hills Resort Vacation Home Ts7718 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. There's a private patio. Conveniences include a dryer and an iron/ironing board.

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Bedroom

Greenway Villa

Private Vacation Home

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Osceola
Greenway Villa Location
With a stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This golf vacation home is 11.7 mi (18.9 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Greenway Villa Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Greenway Villa 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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Fully Booked
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Vacation Homes in Osceola

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