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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
Room

Sprawling Home With Pool, Pool Spa, & Game Room - Athletic Court and gym Access

Vacation Home

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Osceola
Sprawling Home With Pool, Pool Spa, & Game Room - Athletic Court and gym Access 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 7.5 mi (12 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Sprawling Home With Pool, Pool Spa, & Game Room - Athletic Court and gym Access Facility and Service
Enjoy recreational amenities such as an outdoor tennis court and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Sprawling Home With Pool, Pool Spa, & Game Room - Athletic Court and gym Access Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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Windsor Palms Resort 6 Bedroom with Pool+Spa 6 Home

Vacation Home

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Osceola
Windsor Palms Resort 6 Bedroom with Pool+Spa 6 Home Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 8.3 mi (13.4 km) from Disney's Hollywood Studios® and 9.3 mi (15 km) from Disney's Animal Kingdom® Theme Park.

Windsor Palms Resort 6 Bedroom with Pool+Spa 6 Home 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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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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Dog-friendly Townhome w/ Private Pool & Resort Water Park - Close to Disney

Vacation Home

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Osceola
Dog-friendly Townhome w/ Private Pool & Resort Water Park - Close to Disney Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 11.3 mi (18.2 km) from Old Town and 11.4 mi (18.4 km) from ESPN Wide World of Sports Complex.

Dog-friendly Townhome w/ Private Pool & Resort Water Park - Close to Disney Facility and Service
Enjoy recreational amenities such as an outdoor pool and an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Dog-friendly Townhome w/ Private Pool & Resort Water Park - Close to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Firework View 6BR Home Pool/spa/game Near Disney!

Vacation Home

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Osceola
Firework View 6BR Home Pool/spa/game Near Disney! 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 5.4 mi (8.7 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.1 km) from Disney's Hollywood Studios®.

Firework View 6BR Home Pool/spa/game Near Disney! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an outdoor tennis court. This vacation home also features complimentary wireless internet access and an arcade/game room.

Firework View 6BR Home Pool/spa/game Near Disney! 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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Bedroom

Windsor at Westside IHR 4009

Vacation Home

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Osceola
Windsor at Westside IHR 4009 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 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Windsor at Westside IHR 4009 Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Windsor at Westside IHR 4009 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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Spacious Townhouse With Private Patio and Resort Amenites

Vacation Home

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Osceola
Spacious Townhouse With Private Patio and Resort Amenites Location
When you stay at this condo in Four Corners, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This condo is 10.9 mi (17.6 km) from Walt Disney World® Resort and 11.9 mi (19.2 km) from Old Town.

Spacious Townhouse With Private Patio and Resort Amenites Facility and Service
Be sure to enjoy recreational amenities, including a hot tub, an outdoor tennis court, and a fitness center. This condo also features complimentary wireless internet access and an arcade/game room.

Spacious Townhouse With Private Patio and Resort Amenites Rooms
Make yourself comfortable in your individually decorated condo. The bathroom has a bathtub or shower.

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Others

Grhsec8402 - Emerald Island Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhsec8402 - Emerald Island Resort - 6 Bed 6 Baths House Location
When you stay at this vacation home in Kissimmee, you'll be on the waterfront, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf vacation home is 6.8 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Grhsec8402 - Emerald Island Resort - 6 Bed 6 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.

Grhsec8402 - Emerald Island Resort - 6 Bed 6 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
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Others

Ip60347 - Lake Berkley - 3 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ip60347 - Lake Berkley - 3 Bed 2.5 Baths Townhome Location
When you stay at this vacation home in Kissimmee, you'll be on the waterfront, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 8.9 mi (14.3 km) from ESPN Wide World of Sports Complex and 9 mi (14.5 km) from Disney Springs™.

Ip60347 - Lake Berkley - 3 Bed 2.5 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60347 - Lake Berkley - 3 Bed 2.5 Baths Townhome Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A flat-screen television with cable programming is available for your entertainment, and a video-game console is also provided.

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Others

Luxury Lakeview Retreat at Terra Verde Resort

Vacation Home

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Osceola
Luxury Lakeview Retreat at Terra Verde Resort 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 8.6 mi (13.8 km) from Disney Springs™ and 8.9 mi (14.3 km) from Walt Disney World® Resort.

Luxury Lakeview Retreat at Terra Verde Resort Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Luxury Lakeview Retreat at Terra Verde Resort Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

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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Room

8904-TropicalHaven

Vacation Home

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Osceola
8904-TropicalHaven 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 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

8904-TropicalHaven Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

8904-TropicalHaven Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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Room

Bright Modern Home @storey Lake

Vacation Home

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Osceola
Bright Modern Home @storey Lake Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.4 mi (12 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

Bright Modern Home @storey Lake 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 an arcade/game room and barbecue grills.

Bright Modern Home @storey Lake Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Food & Drinks

Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse 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.

Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse 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.

Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

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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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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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Room

Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102

Vacation Home

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Osceola
Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, 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 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex.

Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Family & Kids

Family-friendly Luxury Home With Private Pool

Vacation Home

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Osceola
Family-friendly Luxury Home With Private Pool 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 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Family-friendly Luxury Home With Private Pool Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Family-friendly Luxury Home With Private Pool 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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Bedroom

4200 Paragraph Drive

Vacation Home

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Osceola
4200 Paragraph Drive 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 family-friendly vacation home is 7.5 mi (12 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

4200 Paragraph Drive Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a lazy river, and a waterslide. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

4200 Paragraph Drive Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

Restaurant and Cafe
At this vacation home, enjoy a satisfying meal at the restaurant.

See details
3.0/5
Fully Booked
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Vacation Homes in Osceola

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