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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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Stunning 4 Bd Close To Disney @ Magic Village 3247

Vacation Home

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Osceola
Stunning 4 Bd Close To Disney @ Magic Village 3247 Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Walt Disney World® Resort and 8 minutes from Old Town. This luxury vacation home is 4.7 mi (7.5 km) from ESPN Wide World of Sports Complex and 5.2 mi (8.3 km) from Disney's Hollywood Studios®.

Stunning 4 Bd Close To Disney @ Magic Village 3247 Facility and Service
Enjoy recreation amenities such as a water park (surcharge) or take in the view from a garden. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Stunning 4 Bd Close To Disney @ Magic Village 3247 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. Wired and wireless internet access is complimentary, while a 60-inch Smart television with cable programming provides entertainment. Conveniences include a safe and a desk, and you can also request a rollaway/extra bed (surcharge).

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4.3/5
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Luxurious 6bd Pool Haven Refreshing And Chic-4464n 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Luxurious 6bd Pool Haven Refreshing And Chic-4464n 6 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Veranda Palms), you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.7 mi (10.9 km) from Disney Springs™ and 7.8 mi (12.5 km) from Walt Disney World® Resort.

Luxurious 6bd Pool Haven Refreshing And Chic-4464n 6 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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Ultimate 8BR Family Fun in Resort Near Disney!

Vacation Home

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Osceola
Ultimate 8BR Family Fun in Resort Near Disney! 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 mi (16.1 km) from ESPN Wide World of Sports Complex and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Ultimate 8BR Family Fun in Resort Near Disney! Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Ultimate 8BR Family Fun in Resort Near Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private balcony or patio. The bathroom has a bathtub or shower and designer toiletries.

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Exterior & Views

5BR Pool Home in Storey Lake by SHV-4817

Private Vacation Home

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Osceola
5BR Pool Home in Storey Lake by SHV-4817 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 mi (9.7 km) from Disney Springs��� and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

5BR Pool Home in Storey Lake by SHV-4817 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

5BR Pool Home in Storey Lake by SHV-4817 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private furnished balcony. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Grhcup8953 - Paradise Palms Resort - 6 Bed 5 Baths House

Vacation Home

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Osceola
Grhcup8953 - Paradise Palms Resort - 6 Bed 5 Baths House 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 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Grhcup8953 - Paradise Palms Resort - 6 Bed 5 Baths House Facility and Service
Dip into one of the 2 hot tubs or enjoy other recreational amenities including a complimentary water park and an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcup8953 - Paradise Palms Resort - 6 Bed 5 Baths House 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. Quench your thirst with your favorite drink at the poolside bar.

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Room

Wilmington Grand Escape

Vacation Home

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Osceola
Wilmington Grand Escape Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly 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.

Wilmington Grand Escape Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional features at this vacation home include an arcade/game room and gas grills.

Wilmington Grand Escape Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

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Others

Upstay - Guest Home w Cinema Theme Rooms

Vacation Home

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Osceola
Upstay - Guest Home w Cinema Theme Rooms 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 8.6 mi (13.9 km) from Disney Springs™ and 9.4 mi (15.1 km) from ESPN Wide World of Sports Complex.

Upstay - Guest Home w Cinema Theme Rooms Facility and Service
Enjoy recreational amenities such as an outdoor pool and an indoor pool.

Upstay - Guest Home w Cinema Theme Rooms Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Windsor Hills Resort 5 Bedroom Home with Game Room 5 Home

Vacation Home

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Osceola
Windsor Hills Resort 5 Bedroom Home with Game Room 5 Home 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 vacation home is 5.2 mi (8.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Disney's Hollywood Studios®.

Windsor Hills Resort 5 Bedroom Home with Game Room 5 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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1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center.

1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a DVD player. There's a private patio. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Champions Gate Resort

Vacation Home

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Osceola
Champions Gate Resort 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 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Champions Gate Resort Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include complimentary wireless internet access and a vending machine.

Champions Gate Resort Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a washer/dryer, and housekeeping is provided on a limited basis.

Restaurant and Cafe
Quench your thirst with your favorite drink at the poolside bar.

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2.8/5
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Living area

Charming 4Bd w/ Pool @ Storey Lake Resort Orlando 4861

Vacation Home

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Osceola
Charming 4Bd w/ Pool @ Storey Lake Resort Orlando 4861 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.5 mi (8.9 km) from Disney Springs™ and 6.6 mi (10.6 km) from Walt Disney World® Resort.

Charming 4Bd w/ Pool @ Storey Lake Resort Orlando 4861 Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and an indoor pool. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Charming 4Bd w/ Pool @ Storey Lake Resort Orlando 4861 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 DVD player and cable programming provide entertainment.

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3.8/5
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Interior

Special Offer Great House w Pvt Pool at Champions Gate

Vacation Home

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Osceola
Special Offer Great House w Pvt Pool at Champions Gate Location
With a stay at this villa in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This villa is 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Special Offer Great House w Pvt Pool at Champions Gate Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Exterior & Views

8054 Hidden Gem

Vacation Home

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Osceola
8054 Hidden Gem Location
With a stay at this vacation home in Kissimmee, you'll be a 2-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This vacation home is 6.8 mi (10.9 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

8054 Hidden Gem Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

8054 Hidden Gem Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. A 42-inch flat-screen television is provided, with digital programming available. Conveniences include a microwave and a coffee/tea maker.

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Bedroom

Private Pool Home-popular Resort Near Disney!

Vacation Home

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Osceola
Private Pool Home-popular Resort Near Disney! Location
With a stay at this vacation home in Kissimmee (Lake Berkley), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.3 mi (15 km) from Disney Springs™ and 9.5 mi (15.3 km) from Walt Disney World® Resort.

Private Pool Home-popular Resort Near Disney! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Private Pool Home-popular Resort Near Disney! Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private hot tub and a flat-screen TV. A kitchen makes it easy to prepare your meals. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment.

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Room

Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat

Vacation Home

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Osceola
Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat 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 Old Town. This vacation home is 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.4 km) from Disney's Hollywood Studios®.

Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat Facility and Service
Take advantage of recreation opportunities such as a sauna, or other amenities including complimentary wireless internet access and an arcade/game room.

Emerald Magic Retreat - Minutes to Disney! Emerald Island Pool Home Retreat Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Heaven On Earth Private Home

Vacation Home

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Osceola
Heaven On Earth Private Home Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 2-minute drive from Reunion Resort Golf Course and 9 minutes from ChampionsGate Golf Club. This vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.9 mi (14.4 km) from ESPN Wide World of Sports Complex.

Heaven On Earth Private Home Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, a picnic area, and charcoal grills.

Heaven On Earth Private Home Rooms
Your vacation home features a flat-screen TV. Complimentary wireless internet access is available to keep you connected. Conveniences include a safe and a washer/dryer.

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5.0/5
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2940 PS - BR 5 - Relax Cozy Place Near Disney

Vacation Home

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Osceola
2940 PS - BR 5 - Relax Cozy Place Near Disney 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 7.5 mi (12 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

2940 PS - BR 5 - Relax Cozy Place Near Disney Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center.

2940 PS - BR 5 - Relax Cozy Place Near Disney Rooms
Make yourself comfortable in your vacation home.

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Corvette Cove

Vacation Home

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Osceola
Corvette Cove Location
With a stay at this vacation home in Kissimmee, you'll be a 2-minute drive from Old Town and 10 minutes from Walt Disney World® Resort. This vacation home is 4.8 mi (7.8 km) from ESPN Wide World of Sports Complex and 4.9 mi (7.8 km) from Disney's Hollywood Studios®.

Corvette Cove Facility and Service
Dip into one of the 2 outdoor pools or enjoy other recreational amenities including a waterslide and a fitness center.

Corvette Cove Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

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Windsor Palms Resort 5 Bedroom Home with Game Room 5 Home

Vacation Home

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Osceola
Windsor Palms Resort 5 Bedroom Home with Game Room 5 Home 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 8.2 mi (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

Windsor Palms Resort 5 Bedroom Home with Game Room 5 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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Sport & Beauty

Ev216592 - Windsor At Westside Resort - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Ev216592 - Windsor At Westside Resort - 5 Bed 4 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Ev216592 - Windsor At Westside Resort - 5 Bed 4 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. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ev216592 - Windsor At Westside Resort - 5 Bed 4 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. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Vacation Homes in Osceola

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