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Vacation Homes in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
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Emerald Island Retreat Near Parks

Vacation Home

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Osceola
Emerald Island Retreat Near Parks Location
When you stay at this vacation home in Kissimmee, you'll be near the airport, within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 7.3 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.5 km) from Disney's Hollywood Studios®.

Emerald Island Retreat Near Parks Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Emerald Island Retreat Near Parks Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and an outdoor private hot tub. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 55-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave, as well as a phone with free local calls.

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Bright Chic Oasis With Private Pool and Spa at Reunion

Vacation Home

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Osceola
Bright Chic Oasis With Private Pool and Spa at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Walt Disney World® Resort and Reunion Resort Golf Course. This vacation home is 9.4 mi (15.1 km) from ESPN Wide World of Sports Complex and 9.9 mi (15.9 km) from Disney's Hollywood Studios®.

Bright Chic Oasis With Private Pool and Spa 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.

Bright Chic Oasis With Private Pool and Spa at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis

Vacation Home

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Osceola
Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 2-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This vacation home is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Old Town.

Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Lobby

Big Family Home! Game Room Sleeps 26!

Vacation Home

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Osceola
Big Family Home! Game Room Sleeps 26! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 9.2 mi (14.8 km) from Disney Springs™ and 10.2 mi (16.4 km) from Walt Disney World® Resort.

Big Family Home! Game Room Sleeps 26! 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.

Big Family Home! Game Room Sleeps 26! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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5Br Kissimmee Home W/ Pool & Game Room Fun

Vacation Home

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Osceola
5Br Kissimmee Home W/ Pool & Game Room Fun Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This family-friendly vacation home is 6.9 mi (11 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.4 km) from Old Town.

5Br Kissimmee Home W/ Pool & 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.

5Br Kissimmee Home W/ Pool & Game Room Fun Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment.

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Lobby

Bengal Court Reserve

Vacation Home

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Osceola
Bengal Court Reserve Location
Located in Kissimmee, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This 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.

Bengal Court Reserve Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub.

Bengal Court Reserve 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. Conveniences include a coffee/tea maker and a washer/dryer.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Others

Lovely 5br Townhouse At Windsor At Westside 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Lovely 5br Townhouse At Windsor At Westside 5 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Lovely 5br Townhouse At Windsor At Westside 5 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Windsor at Westside Resort 8 Bedroom Pool+Spa Home 8 Home

Vacation Home

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Osceola
Windsor at Westside Resort 8 Bedroom Pool+Spa Home 8 Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Windsor at Westside Resort 8 Bedroom Pool+Spa Home 8 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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Others

5BR Bear's Den Estate Private Pool & Game Room

Vacation Home

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Osceola
5BR Bear's Den Estate Private Pool & Game Room 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 mi (11.3 km) from Walt Disney World® Resort and 9 mi (14.5 km) from Old Town.

5BR Bear's Den Estate Private Pool & Game Room 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 Estate Private Pool & Game Room Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Lobby

Delightful Lakefront Townhome With Pool, Volleyball, Fast Wifi & AC

Vacation Home

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Osceola
Delightful Lakefront Townhome With Pool, Volleyball, Fast Wifi & AC Location
With a stay at this vacation home in Kissimmee (Trafalgar Village), you'll be within a 15-minute drive of Medieval Times and Green Meadows Petting Farm. This vacation home is 11 mi (17.7 km) from Old Town and 11.7 mi (18.8 km) from Reunion Resort Golf Course.

Delightful Lakefront Townhome With Pool, Volleyball, Fast Wifi & AC 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.

Delightful Lakefront Townhome With Pool, Volleyball, Fast Wifi & AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

284 Encore at Reunion

Vacation Home

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Osceola
284 Encore at Reunion Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This golf vacation home is 5.7 mi (9.1 km) from Walt Disney World® Resort and 7.9 mi (12.7 km) from ESPN Wide World of Sports Complex.

284 Encore at Reunion Rooms
Make yourself comfortable in this vacation home, which features a private pool and a Smart TV. Wireless internet access (surcharge) is available to keep you connected.

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Game room

Stunning 5 Bd Home w/ Pool Close to Disney 7420

Vacation Home

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Osceola
Stunning 5 Bd Home w/ Pool Close to Disney 7420 Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This luxury vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.7 mi (15.7 km) from ESPN Wide World of Sports Complex.

Stunning 5 Bd Home w/ Pool Close to Disney 7420 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this vacation home include concierge services, a television in a common area, and charcoal grills.

Stunning 5 Bd Home w/ Pool Close to Disney 7420 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A 60-inch Smart television with cable programming provides entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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3.7/5
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Others

Ov3781 - Windsor Hills Resort - 3 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov3781 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov3781 - Windsor Hills Resort - 3 Bed 2 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 hot tub 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.

Ov3781 - Windsor Hills Resort - 3 Bed 2 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 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. Wrap up your day with a drink at the bar/lounge.

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The Tranquil Townhome - Elegant Townhome in Reunion Resort

Vacation Home

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Osceola
The Tranquil Townhome - Elegant Townhome in Reunion Resort Location
Located in Kissimmee (Reunion), The Tranquil Townhome - Elegant Townhome in Reunion Resort is within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14.1 km) from Old Town.

The Tranquil Townhome - Elegant Townhome in Reunion Resort Rooms
Make yourself at home in one of the individually decorated guestrooms. Bathrooms with bathtubs or showers are provided.

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Others

Villa Victória - Encantada Resort

Vacation Home

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Osceola
Villa Victória - Encantada Resort 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 7.2 mi (11.6 km) from Disney's Animal Kingdom® Theme Park and 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex.

Villa Victória - Encantada Resort Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Villa Victória - Encantada Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a dryer and an iron/ironing board, and housekeeping is provided once per stay.

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Spacious 9-bedroom Orlando vacation home

Vacation Home

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Osceola
Spacious 9-bedroom Orlando vacation home Location
When you stay at this apartment in Kissimmee, you'll be in the entertainment district, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This apartment is 10 mi (16.1 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Spacious 9-bedroom Orlando vacation home Facility and Service
Enjoy recreational amenities such as an indoor pool and a waterslide.

Spacious 9-bedroom Orlando vacation home Rooms
Make yourself comfortable in your apartment. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and an all-in-one washing machine and dryer.

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Exterior & Views

Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning

Vacation Home

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Osceola
Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This family-friendly vacation home is 5.2 mi (8.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including complimentary wireless internet access.

Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private lanai. Complimentary wireless internet access keeps you connected, and a video-game console is provided for your entertainment. Conveniences include a washing machine and a ceiling fan.

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Others

Compass Bay- 4 Bedroom Townhome - 1954CY 4 Townhouse by RedAwning

Vacation Home

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Osceola
Compass Bay- 4 Bedroom Townhome - 1954CY 4 Townhouse by RedAwning 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 5.5 mi (8.8 km) from Disney Springs™ and 6.2 mi (9.9 km) from Walt Disney World® Resort.

Compass Bay- 4 Bedroom Townhome - 1954CY 4 Townhouse by RedAwning Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Bedroom

Championsgate 6BR Luxury Home Pool Spa Near Disney

Vacation Home

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Osceola
Championsgate 6BR Luxury Home Pool Spa Near Disney 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 12.1 mi (19.4 km) from Old Town and 12.8 mi (20.7 km) from ESPN Wide World of Sports Complex.

Championsgate 6BR Luxury Home Pool Spa Near Disney 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.

Championsgate 6BR Luxury Home Pool Spa Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries.

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Beautiful & Spacious Resort Home in the Heart of Central FL

Vacation Home

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Osceola
Beautiful & Spacious Resort Home in the Heart of Central FL Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and Disney Springs™. This vacation home is 8.6 mi (13.8 km) from ESPN Wide World of Sports Complex and 9 mi (14.4 km) from Disney's Hollywood Studios®.

Beautiful & Spacious Resort Home in the Heart of Central FL 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.

Beautiful & Spacious Resort Home in the Heart of Central FL 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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