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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
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4BR Retreat in Champions Gate w/ Private Pool

Vacation Home

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Osceola
4BR Retreat in Champions Gate w/ Private Pool 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 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

4BR Retreat in Champions Gate w/ Private Pool Facility and Service
Take advantage of recreation opportunities such as an outdoor tennis court, or other amenities including complimentary wireless internet access and an arcade/game room.

4BR Retreat in Champions Gate w/ Private Pool 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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Nestle Away at Poplar Way

Private Vacation Home

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Osceola
Nestle Away at Poplar Way Location
Located in Kissimmee, this vacation home is in a shopping district, within a 10-minute drive of Lake Tohopekaliga and Kissimmee Oaks Golf Course. This vacation home is 12.9 mi (20.8 km) from Old Town and 16.1 mi (25.9 km) from Disney Springs™.

Nestle Away at Poplar Way Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Nestle Away at Poplar Way Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

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Solara Resort 8 Bedroom Private Pool Home 8 Home

Vacation Home

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Osceola
Solara Resort 8 Bedroom Private Pool Home 8 Home 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 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11 mi (17.7 km) from ESPN Wide World of Sports Complex.

Solara Resort 8 Bedroom Private Pool Home 8 Home 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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Others

Ov2575 - Windsor Palms Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov2575 - Windsor Palms Resort - 4 Bed 3 Baths Townhome 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 7 mi (11.3 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Ov2575 - Windsor Palms Resort - 4 Bed 3 Baths Townhome 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.

Ov2575 - Windsor Palms Resort - 4 Bed 3 Baths Townhome 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 with cable programming is available for your entertainment, and a DVD player is also provided.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Family & Kids

Ov2644 - Emerald Island - 3 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ov2644 - Emerald Island - 3 Bed 2.5 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 golf vacation home is 6.9 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Ov2644 - Emerald Island - 3 Bed 2.5 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov2644 - Emerald Island - 3 Bed 2.5 Baths Townhome Rooms
Make yourself comfortable in this individually decorated 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 washer/dryer.

Restaurant and Cafe
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Bedroom

Ovm2344 - Emerald Island - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ovm2344 - Emerald Island - 4 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 6.9 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Ovm2344 - Emerald Island - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and an arcade/game room.

Ovm2344 - Emerald Island - 4 Bed 3 Baths Townhome 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
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

See details
Fully Booked
Let's check on other dates!
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Champions Gate, Pool, Themed Rooms

Vacation Home

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Osceola
Champions Gate, Pool, Themed Rooms Location
With a stay at Champions Gate, Pool, Themed Rooms in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This family-friendly vacation home is 12.3 mi (19.8 km) from Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

Champions Gate, Pool, Themed Rooms Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools.

Champions Gate, Pool, Themed Rooms Rooms
Make yourself at home in one of the 5 air-conditioned rooms featuring private pools. Rooms have private furnished patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected.

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5.0/5
Fully Booked
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Modern Townhouse Near Disney W/ Private Pool 8523

Vacation Home

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Osceola
Modern Townhouse Near Disney W/ Private Pool 8523 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 6.9 mi (11 km) from Disney's Animal Kingdom® Theme Park and 8.1 mi (13 km) from ESPN Wide World of Sports Complex.

Modern Townhouse Near Disney W/ Private Pool 8523 Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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5.0/5
Fully Booked
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Solara Joy Disney-themed Retreat in Kissimmee With Stellar Resort Amenities

Vacation Home

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Osceola
Solara Joy Disney-themed Retreat in Kissimmee With Stellar Resort Amenities Location
When you stay at Solara Joy Disney-themed Retreat in Kissimmee With Stellar Resort Amenities in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18.1 km) from ESPN Wide World of Sports Complex.

Solara Joy Disney-themed Retreat in Kissimmee With Stellar Resort Amenities Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Solara Joy Disney-themed Retreat in Kissimmee With Stellar Resort Amenities Rooms
Make yourself at home in one of the individually decorated guestrooms. Bathrooms with bathtubs or showers are provided.

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Cozy 3BR Townhome 5 Miles From Disney

Vacation Home

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Osceola
Cozy 3BR Townhome 5 Miles From Disney 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 mi (9.7 km) from Walt Disney World® Resort and 8.3 mi (13.3 km) from ESPN Wide World of Sports Complex.

Cozy 3BR Townhome 5 Miles From Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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

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Exterior & Views

Cool and Modern 5 Bed 4 Ba Game Room Pool Spa 4724sh

Vacation Home

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Osceola
Cool and Modern 5 Bed 4 Ba Game Room Pool Spa 4724sh Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly cottage is 6.1 mi (9.8 km) from Disney Springs™ and 6.9 mi (11 km) from ESPN Wide World of Sports Complex.

Cool and Modern 5 Bed 4 Ba Game Room Pool Spa 4724sh Facility and Service
Take time to pamper yourself with a visit to the full-service spa. If you're looking for recreational opportunities, you'll find an outdoor pool and a fitness center. This cottage also features an arcade/game room and barbecue grills.

Cool and Modern 5 Bed 4 Ba Game Room Pool Spa 4724sh Rooms
Make yourself comfortable in this air-conditioned cottage, 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. Conveniences include a dryer and an iron/ironing board.

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Exterior & Views

Terra_verde_137

Vacation Home

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Osceola
Terra_verde_137 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 8.6 mi (13.8 km) from Disney Springs™ and 8.7 mi (14 km) from ESPN Wide World of Sports Complex.

Terra_verde_137 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional features at this vacation home include concierge services, an arcade/game room, and barbecue grills.

Terra_verde_137 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. A private bathroom has a jetted bathtub and a hair dryer.

Restaurant and Cafe
Grab a bite from the snack bar/deli serving guests of this vacation home.

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4.0/5
Fully Booked
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Exterior & Views

9 Bed Home Storey Lake 9 Bedroom Home by RedAwning

Vacation Home

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Osceola
9 Bed Home Storey Lake 9 Bedroom Home 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 6.1 mi (9.9 km) from Disney Springs™ and 7.2 mi (11.5 km) from Walt Disney World® Resort.

9 Bed Home Storey Lake 9 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a microwave. Complimentary wireless internet access is available to keep you connected.

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Others

Champions Gate Vista 1355

Vacation Home

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Osceola
Champions Gate Vista 1355 Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of Old Town and ChampionsGate Golf Club. This golf vacation home is 10.7 mi (17.2 km) from ESPN Wide World of Sports Complex and 10.8 mi (17.4 km) from Walt Disney World® Resort.

Champions Gate Vista 1355 Facility and Service
This smoke-free vacation home features hiking/biking trails nearby.

Champions Gate Vista 1355 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private patio. Wired and wireless internet access is complimentary, and a flat-screen television with satellite programming provides entertainment. The bathroom has a jetted bathtub.

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Tropical Lux

Private Vacation Home

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Osceola
Tropical Lux Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9 mi (14.5 km) from Disney Springs™ and 9.2 mi (14.8 km) from Walt Disney World® Resort.

Tropical Lux Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include a separate sitting area and a microwave.

See details
4.0/5
Fully Booked
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Exterior & Views

The Emerald Cove Best Spot in Kissimmee!

Vacation Home

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Osceola
The Emerald Cove Best Spot in Kissimmee! 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 Mystic Dunes Golf Club. This golf vacation home is 6.6 mi (10.6 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

The Emerald Cove Best Spot in Kissimmee! Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and complimentary use of a nearby fitness facility.

The Emerald Cove Best Spot in Kissimmee! Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private furnished patio. A 42-inch flat-screen television is provided, with digital programming available. Conveniences include a separate sitting area and a microwave.

Important Information
The property will be renovating from October 12 2026 to April 12 2027 (completion date subject to change). The following areas are affected:
  • Exterior
During renovations, the vacation home will make every effort to minimize noise and disturbance.

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Bright and Sunny Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Bright and Sunny Townhouse With Games Room at Reunion Location
Located in Kissimmee (Reunion), this vacation home 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 km) from Old Town.

Bright and Sunny Townhouse With Games Room at Reunion Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

Bright and Sunny Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

4707 4-bdrm'slake Viewgames Roomoutdoor Spa!

Vacation Home

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Osceola
4707 4-bdrm'slake Viewgames Roomoutdoor Spa! 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 spa vacation home is 10.3 mi (16.6 km) from Disney Springs™ and 10.5 mi (16.9 km) from ESPN Wide World of Sports Complex.

4707 4-bdrm'slake Viewgames Roomoutdoor Spa! Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

4707 4-bdrm'slake Viewgames Roomoutdoor Spa! 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, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment.

See details
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Storey Lake Resort 4 Bedroom Private Pool Townhome 4 Townhouse

Vacation Home

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Osceola
Storey Lake Resort 4 Bedroom Private Pool Townhome 4 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 5.4 mi (8.7 km) from Disney Springs™ and 6.5 mi (10.4 km) from Walt Disney World® Resort.

Storey Lake Resort 4 Bedroom Private Pool Townhome 4 Townhouse 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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Fully Booked
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Exterior & Views

Luxury Champions Gate 4 Bedroom Town Home

Vacation Home

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Osceola
Luxury Champions Gate 4 Bedroom Town 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 family-friendly vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Luxury Champions Gate 4 Bedroom Town Home Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Luxury Champions Gate 4 Bedroom Town Home 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.

See details
Fully Booked
Let's check on other dates!
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Vacation Homes in Osceola

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