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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
Exterior & Views

Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820

Vacation Home

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Osceola
Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820 Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 6.2 mi (10 km) from Walt Disney World® Resort.

Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. 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. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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Lobby

Family Home Boasting Entertainment for Everyone With a Pool

Vacation Home

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Osceola
Family Home Boasting Entertainment for Everyone With a Pool 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 ChampionsGate Golf Club. This vacation home is 9.9 mi (16 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Family Home Boasting Entertainment for Everyone With a Pool 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.

Family Home Boasting Entertainment for Everyone With a Pool Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Pistachio Palace Sleeps 10!

Vacation Home

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Osceola
Pistachio Palace Sleeps 10! 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 Flamingo Crossings Town Center. This golf vacation home is 6.3 mi (10.2 km) from Disney's Animal Kingdom® Theme Park and 7.2 mi (11.7 km) from Old Town.

Pistachio Palace Sleeps 10! 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.

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Lovely 4Bd Townhome Near Disney @ Compass Bay 5122

Vacation Home

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Osceola
Lovely 4Bd Townhome Near Disney @ Compass Bay 5122 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.

Lovely 4Bd Townhome Near Disney @ Compass Bay 5122 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Lovely 4Bd Townhome Near Disney @ Compass Bay 5122 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private hot tub 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 60-inch flat-screen television with cable programming provides entertainment.

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1.5/5
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Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer

Vacation Home

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Osceola
Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer 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 Mystic Dunes Golf Club. This family-friendly vacation home is 11.5 mi (18.6 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Pool

Solara Resort 9 Bedroom Private Pool Home 9 Home

Vacation Home

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Osceola
Solara Resort 9 Bedroom Private Pool Home 9 Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.5 mi (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Solara Resort 9 Bedroom Private Pool Home 9 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

Hideaway Dream 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Hideaway Dream 6 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be 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 9.3 mi (15 km) from Walt Disney World® Resort.

Hideaway Dream 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

4BR Pool Home Rolling Hills by SHV-7979

Private Vacation Home

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Osceola
4BR Pool Home Rolling Hills by SHV-7979 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 vacation home is 6.3 mi (10.1 km) from ESPN Wide World of Sports Complex and 6.6 mi (10.6 km) from Old Town.

4BR Pool Home Rolling Hills by SHV-7979 Rooms
Make yourself comfortable in this vacation home, 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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4.0/5
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Others

5BR Harry Potter Townhouse 15 min to Disney

Vacation Home

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Osceola
5BR Harry Potter Townhouse 15 min to Disney Location
With a stay at this villa in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This villa is 5.1 mi (8.2 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.6 km) from Old Town.

5BR Harry Potter Townhouse 15 min to Disney 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.

5BR Harry Potter Townhouse 15 min to Disney Rooms
Your villa features a Smart TV. 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. Conveniences include a washer/dryer, and a crib/infant bed (complimentary) can be requested.

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Exterior & Views

2735book

Vacation Home

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Osceola
2735book 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 spa 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.

2735book Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

2735book 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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Exterior & Views

9005 Sunshine Ridge Loop

Private Vacation Home

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Osceola
9005 Sunshine Ridge Loop 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 Flamingo Crossings Town Center. This vacation home is 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.5 mi (18.5 km) from Old Town.

9005 Sunshine Ridge Loop Facility and Service
Take advantage of recreation opportunities including an outdoor pool and an indoor pool. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

9005 Sunshine Ridge Loop Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a microwave and a coffee/tea maker.

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Exterior & Views

4BR 3BA Home in Windsor Palms by CV-8115

Vacation Home

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Osceola
4BR 3BA Home in Windsor Palms by CV-8115 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 8.2 mi (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.8 km) from Disney's Animal Kingdom® Theme Park.

4BR 3BA Home in Windsor Palms by CV-8115 Rooms
Make yourself comfortable in this air-conditioned vacation home, 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 keeps you connected, and a DVD player is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Others

Veranda Palm Resort 12br 2486

Vacation Home

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Osceola
Veranda Palm Resort 12br 2486 Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.6 mi (12.2 km) from Disney Springs™ and 8.3 mi (13.3 km) from Walt Disney World® Resort.

Veranda Palm Resort 12br 2486 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.

Veranda Palm Resort 12br 2486 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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Sport & Beauty

Spacious 5 Bed Pool Home With Game Room 5 Bedroom Home

Vacation Home

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Osceola
Spacious 5 Bed Pool Home With Game Room 5 Bedroom 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 11.3 mi (18.1 km) from Walt Disney World® Resort and 11.6 mi (18.7 km) from Old Town.

Spacious 5 Bed Pool Home With Game Room 5 Bedroom Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Beautiful 5 Bed Pool Home At Resort- No Resort Fee 5 Bedroom Townhouse

Vacation Home

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Osceola
Beautiful 5 Bed Pool Home At Resort- No Resort Fee 5 Bedroom Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and ChampionsGate Golf Club. This vacation home is 7.9 mi (12.8 km) from Walt Disney World® Resort and 9.7 mi (15.7 km) from Disney's Animal Kingdom® Theme Park.

Beautiful 5 Bed Pool Home At Resort- No Resort Fee 5 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Food & Drinks

Grhmvd1700 - Champions Gate Resort - 9 Bed 5 Baths House

Vacation Home

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Osceola
Grhmvd1700 - Champions Gate Resort - 9 Bed 5 Baths House 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 11.6 mi (18.6 km) from Old Town and 12.4 mi (19.9 km) from ESPN Wide World of Sports Complex.

Grhmvd1700 - Champions Gate Resort - 9 Bed 5 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1700 - Champions Gate Resort - 9 Bed 5 Baths House 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
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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Room

Theme Dream Lux Vacation Home!

Vacation Home

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Osceola
Theme Dream Lux Vacation Home! 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 Flamingo Crossings Town Center. This vacation home is 10 mi (16 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Theme Dream Lux Vacation Home! 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.

Theme Dream Lux Vacation Home! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Living area

Modern Home, Private Pool. Sleeps 15 Ww102

Vacation Home

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Osceola
Modern Home, Private Pool. Sleeps 15 Ww102 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 ChampionsGate Golf Club. This vacation home is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Modern Home, Private Pool. Sleeps 15 Ww102 Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional features at this vacation home include an arcade/game room and barbecue grills.

Modern Home, Private Pool. Sleeps 15 Ww102 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor At Westside-2112amwjil 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
Windsor At Westside-2112amwjil 7 Bedroom Home 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 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Windsor At Westside-2112amwjil 7 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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Sport & Beauty

Bella Vida 4568 IHR 1021

Vacation Home

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Osceola
Bella Vida 4568 IHR 1021 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 (13.7 km) from Disney Springs™ and 8.6 mi (13.9 km) from ESPN Wide World of Sports Complex.

Bella Vida 4568 IHR 1021 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional features at this vacation home include an arcade/game room and a picnic area.

Bella Vida 4568 IHR 1021 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. 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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Vacation Homes in Osceola

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