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Vacation Homes in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
Sport & Beauty

Paradise Palms- 4 Bed Townhome W-splashpool-3091pp 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Paradise Palms- 4 Bed Townhome W-splashpool-3091pp 4 Bedroom Townhouse by RedAwning 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 mi (13 km) from Disney's Animal Kingdom® Theme Park and 8.9 mi (14.4 km) from ESPN Wide World of Sports Complex.

Paradise Palms- 4 Bed Townhome W-splashpool-3091pp 4 Bedroom Townhouse by RedAwning Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center. Additional amenities at this vacation home include concierge services and an arcade/game room.

Paradise Palms- 4 Bed Townhome W-splashpool-3091pp 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this vacation home, which features a private pool. A kitchen is outfitted with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment. Conveniences include a coffee/tea maker and a washing machine.

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Reunion 5 Bedroom Vacation Home 7824

Vacation Home

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Osceola
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Bedroom

UpstaySpaciousHomePoolHotTubSleeps27

Vacation Home

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Osceola
UpstaySpaciousHomePoolHotTubSleeps27 Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.6 mi (15.5 km) from Disney Springs™ and 10.7 mi (17.2 km) from Walt Disney World® Resort.

UpstaySpaciousHomePoolHotTubSleeps27 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and an indoor pool.

UpstaySpaciousHomePoolHotTubSleeps27 Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and a washer/dryer.

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Exterior & Views

510 BS - 5BD Elegant Escape: Private Haven

Vacation Home

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Osceola
510 BS - 5BD Elegant Escape: Private Haven Location
When you stay at this vacation home in Kissimmee, you'll be on the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.6 mi (12.2 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

510 BS - 5BD Elegant Escape: Private Haven Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

510 BS - 5BD Elegant Escape: Private Haven Rooms
Make yourself comfortable in your vacation home. Conveniences include an electric kettle and an iron/ironing board.

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Others

Champions_gate_1406

Vacation Home

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Osceola
Champions_gate_1406 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 11.6 mi (18.7 km) from Old Town and 12.4 mi (20 km) from ESPN Wide World of Sports Complex.

Champions_gate_1406 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and concierge services.

Champions_gate_1406 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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Sport & Beauty

Ov2681 - Windsor Hills Resort - 3 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov2681 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 5.6 mi (8.9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov2681 - Windsor Hills Resort - 3 Bed 2 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 hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2681 - Windsor Hills Resort - 3 Bed 2 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 washer/dryer.

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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Others

Ov2939 - Windsor Hills Resort - 3 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov2939 - 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 family-friendly 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®.

Ov2939 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and an outdoor pool. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2939 - 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. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Fully Booked
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Others

3BR Townhouse Near Disney Private Pool

Vacation Home

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Osceola
3BR Townhouse Near Disney Private Pool Location
With a stay at this villa in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This villa is 6.8 mi (11 km) from Disney's Animal Kingdom® Theme Park and 8 mi (12.9 km) from ESPN Wide World of Sports Complex.

3BR Townhouse Near Disney Private Pool Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. This villa also features complimentary wireless internet access and an arcade/game room.

3BR Townhouse Near Disney Private Pool Rooms
Your villa features a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Others

Villa Campos- Encantada Resort

Vacation Home

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Osceola
Villa Campos- 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 mi (11.3 km) from Disney's Animal Kingdom® Theme Park and 8.2 mi (13.3 km) from ESPN Wide World of Sports Complex.

Villa Campos- Encantada Resort Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Housekeeping is provided once per stay, and a rollaway/extra bed can be requested.

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Modern Abode With Private Pool and Spa in Encore

Vacation Home

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Osceola
Modern Abode With Private Pool and Spa in Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 7.8 mi (12.6 km) from ESPN Wide World of Sports Complex.

Modern Abode With Private Pool and Spa in Encore 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 and an arcade/game room.

Modern Abode With Private Pool and Spa in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!!

Vacation Home

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Osceola
Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!! Location
With a stay at Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!! in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Disney Springs™. This vacation home is 8.3 mi (13.3 km) from ESPN Wide World of Sports Complex and 8.5 mi (13.7 km) from Walt Disney World® Resort.

Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!! Rooms
Make yourself at home in of the guestrooms featuring private pools. Complimentary wireless internet access is available to keep you connected.

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Others

Windsor At Westside-2167amtjgi 8 Bedroom Home by RedAwning

Vacation Home

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Osceola
Windsor At Westside-2167amtjgi 8 Bedroom Home by RedAwning 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 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Windsor At Westside-2167amtjgi 8 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly

Vacation Home

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Osceola
Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly 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 8.5 mi (13.6 km) from Disney Springs™ and 8.9 mi (14.4 km) from Walt Disney World® Resort.

Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Luxury 4 Bedroom Storey Lake Townhome 2444Reading 4 Townhouse

Vacation Home

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Osceola
Luxury 4 Bedroom Storey Lake Townhome 2444Reading 4 Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.9 mi (9.5 km) from Disney Springs™ and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

Luxury 4 Bedroom Storey Lake Townhome 2444Reading 4 Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Spacious House With Private Pool and Spa at Encore

Vacation Home

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Osceola
Spacious House With Private Pool and Spa at Encore Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This villa is 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

Spacious House With Private Pool and Spa at Encore Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious House With Private Pool and Spa at Encore Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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Room

Amazing Hidden Gem Min to Disney 139

Vacation Home

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Osceola
Amazing Hidden Gem Min to Disney 139 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (8 km) from ESPN Wide World of Sports Complex and 5.6 mi (9 km) from Disney's Hollywood Studios®.

Amazing Hidden Gem Min to Disney 139 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Spacious 5bd Pool Th, Champions Gate-1610mvd 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Spacious 5bd Pool Th, Champions Gate-1610mvd 5 Bedroom Townhouse by RedAwning Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Spacious 5bd Pool Th, Champions Gate-1610mvd 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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1486 Moon Valley Drive

Private Vacation Home

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Osceola
1486 Moon Valley Drive Location
With a stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This vacation home is 11.8 mi (18.9 km) from Old Town and 12.7 mi (20.5 km) from Walt Disney World® Resort.

1486 Moon Valley Drive Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an indoor pool, and a fitness center.

1486 Moon Valley Drive Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Sport & Beauty

Fv50308 - Paradise Palms - 5 Bed 3 Baths Townhome

Vacation Home

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Osceola
Fv50308 - Paradise Palms - 5 Bed 3 Baths Townhome 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 family-friendly vacation home is 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Fv50308 - Paradise Palms - 5 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 an arcade/game room.

Fv50308 - Paradise Palms - 5 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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Surf Shack With Games Room at Reunion

Vacation Home

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Osceola
Surf Shack With Games Room at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 3-minute drive from Reunion Resort Golf Course and 7 minutes from ChampionsGate Golf Club. This vacation home is 7.7 mi (12.3 km) from Walt Disney World® Resort and 10.3 mi (16.6 km) from Old Town.

Surf Shack With Games Room at Reunion Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Surf Shack With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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Vacation Homes in Osceola

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