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Vacation Homes in Osceola

Osceola
Thu, 19 Nov 2026 - Fri, 20 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
Exterior & Views

7BR 4.5BA Home in Emerald Island Resort by CV-2767

Vacation Home

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Osceola
7BR 4.5BA Home in Emerald Island Resort by CV-2767 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 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

7BR 4.5BA Home in Emerald Island Resort by CV-2767 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

7BR 4.5BA Home in Emerald Island Resort by CV-2767 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 video-game console is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Bedroom

4BR Tropical Storey Lake Townhome Private Pool

Vacation Home

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Osceola
4BR Tropical Storey Lake Townhome Private Pool 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 7.3 mi (11.8 km) from Disney Springs™ and 8.4 mi (13.5 km) from Walt Disney World® Resort.

4BR Tropical Storey Lake Townhome Private Pool Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

4BR Tropical Storey Lake Townhome Private Pool Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private furnished balcony/patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Room

Luxurious Family Retreat w/ Private Pool & Resort Access

Vacation Home

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Osceola
Luxurious Family Retreat w/ Private Pool & Resort Access 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 6.4 mi (10.3 km) from Disney Springs™ and 7.4 mi (11.9 km) from Walt Disney World® Resort.

Luxurious Family Retreat w/ Private Pool & Resort Access Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

American Dream

Vacation Home

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Osceola
American Dream 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 11.1 mi (17.8 km) from ESPN Wide World of Sports Complex.

American Dream Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

American Dream Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a sofa bed, as well as a phone with free local calls.

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Amazing Townhouse close to Disney 2 Bed 2.5 Bath

Vacation Home

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Osceola
Amazing Townhouse close to Disney 2 Bed 2.5 Bath provides flawless service and all the necessary facilities for visitors.Guests can avail parking facilities at the private villa.Kindly note that smoking is prohibited in the private villa to ensure fresher air for all visitors. At Amazing Townhouse close to Disney 2 Bed 2.5 Bath, every guestroom is provided with convenient amenities and fittings to ensure a comfortable stay. Certain rooms boast in-room amusement features such as television and cable TV, offering guests an enjoyable stay.Essential restroom facilities are equally significant, and at the private villa, some visitor bathrooms offer a hair dryer to enhance your experience. At Amazing Townhouse close to Disney 2 Bed 2.5 Bath, guests can take pleasure in the delightful recreational amenities provided for their entertainment.Conclude your holiday experience perfectly by visiting hot tub before you depart. Discover the fitness amenities at private villa to maintain your health and strength during your getaway.
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8056 King Palm Circle

Vacation Home

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Osceola
8056 King Palm Circle 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 (13.3 km) from Disney's Hollywood Studios® and 9.2 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

8056 King Palm Circle Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

8056 King Palm Circle Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony or patio. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Exterior & Views

Pompano Place 3 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Pompano Place 3 Bedroom Townhouse 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 8.6 mi (13.8 km) from ESPN Wide World of Sports Complex and 8.6 mi (13.9 km) from Disney Springs™.

Pompano Place 3 Bedroom Townhouse by RedAwning 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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Gorgeous 4Bd w/ Screened Pool Close to Disney 4289

Vacation Home

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Osceola
Gorgeous 4Bd w/ Screened Pool Close to Disney 4289 Location
Located in Kissimmee, this vacation home is 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.

Gorgeous 4Bd w/ Screened Pool Close to Disney 4289 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Gorgeous 4Bd w/ Screened Pool Close to Disney 4289 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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5.0/5
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Exterior & Views

Amazing Story Lake Town Home With Pool 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Amazing Story Lake Town Home With Pool 4 Bedroom Townhouse 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 mi (9.6 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

Amazing Story Lake Town Home With Pool 4 Bedroom Townhouse 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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Amazing 3/2 Townhome With Lake View at Terra Verde!!

Private Vacation Home

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Osceola
Amazing 3/2 Townhome With Lake View at Terra Verde!! Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Walt Disney World® Resort. This vacation home is 9 mi (14.4 km) from Disney Springs�� and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Amazing 3/2 Townhome With Lake View at Terra Verde!! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Amazing 3/2 Townhome With Lake View at Terra Verde!! 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 phone, as well as an electric kettle and a dryer.

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Family & Kids

Grhmyr1465 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhmyr1465 - Champions Gate Resort - 6 Bed 6 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 11.8 mi (19 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Grhmyr1465 - Champions Gate 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. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmyr1465 - Champions Gate Resort - 6 Bed 6 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 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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Sport & Beauty

Veranda Palms Resort

Vacation Home

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Osceola
Veranda Palms Resort Location
With a stay at Veranda Palms Resort in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.9 mi (11.2 km) from Disney Springs™ and 7.9 mi (12.8 km) from ESPN Wide World of Sports Complex.

Veranda Palms Resort 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, tour/ticket assistance, and barbecue grills. Guests can catch a ride to nearby destinations on the area shuttle (surcharge).

Veranda Palms Resort Rooms
Make yourself at home in one of the 14 individually decorated guestrooms, featuring kitchens with refrigerators and ovens. Rooms have private patios. Complimentary wireless internet access is available to keep you connected. Conveniences include separate sitting areas and microwaves.

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3.2/5
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Grhcap8883 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhcap8883 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse 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 8.2 mi (13.3 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.7 km) from ESPN Wide World of Sports Complex.

Grhcap8883 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse 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.

Grhcap8883 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Banana Palm Paradise 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
Banana Palm Paradise 5 Bedroom Home 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 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.7 km) from ESPN Wide World of Sports Complex.

Banana Palm Paradise 5 Bedroom Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Banana Palm Paradise 5 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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Bedroom

4bed 3Ba Champions Gate Pool Home

Vacation Home

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Osceola
4bed 3Ba Champions Gate Pool Home 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 7.8 mi (12.5 km) from Disney Springs™ and 8.4 mi (13.5 km) from Walt Disney World® Resort.

4bed 3Ba Champions Gate Pool Home Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

4bed 3Ba Champions Gate Pool 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.

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Exterior & Views

San Christabolo

Vacation Home

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Osceola
San Christabolo Location
With a stay at this vacation home in Kissimmee (Venetian Bay Villages), 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 10.4 mi (16.7 km) from Walt Disney World® Resort.

San Christabolo Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

San Christabolo Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant, or stay in and take advantage of the vacation home's room service.

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Bedroom

6BR 4BA Home in Windsor Hills by CV-2537

Vacation Home

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Osceola
6BR 4BA Home in Windsor Hills by CV-2537 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 Mystic Dunes Golf Club. This vacation home is 5.9 mi (9.5 km) from ESPN Wide World of Sports Complex and 6.5 mi (10.4 km) from Old Town.

6BR 4BA Home in Windsor Hills by CV-2537 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including barbecue grills.

6BR 4BA Home in Windsor Hills by CV-2537 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 video-game console is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Snowbird-friendly Home Near Disney With Private Pool, Lanai, Tennis, Basketball

Vacation Home

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Osceola
Snowbird-friendly Home Near Disney With Private Pool, Lanai, Tennis, Basketball 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 Flamingo Crossings Town Center. This vacation home is 11.3 mi (18.2 km) from Walt Disney World® Resort and 13.1 mi (21.1 km) from Disney's Animal Kingdom® Theme Park.

Snowbird-friendly Home Near Disney With Private Pool, Lanai, Tennis, Basketball Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Snowbird-friendly Home Near Disney With Private Pool, Lanai, Tennis, Basketball Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Grhec9113 - Champions Gate Resort - 4 Bed 3 Baths House

Vacation Home

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Osceola
Grhec9113 - Champions Gate Resort - 4 Bed 3 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 11.8 mi (18.9 km) from Old Town and 12.5 mi (20.2 km) from ESPN Wide World of Sports Complex.

Grhec9113 - Champions Gate Resort - 4 Bed 3 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhec9113 - Champions Gate Resort - 4 Bed 3 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 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

Lago Vista Resort

Vacation Home

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Osceola
Lago Vista Resort Location
With a stay at this vacation home in Kissimmee (Buena Ventura Lakes), you'll be within a 15-minute drive of Florida Mall and Houston Astros Spring Training. This vacation home is 13.8 mi (22.2 km) from Orange County Convention Center and 14 mi (22.5 km) from Universal Epic Universe.

Lago Vista Resort Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and a picnic area.

Lago Vista Resort Rooms
Make yourself comfortable in this air-conditioned 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 phone, as well as a microwave and an iron/ironing board.

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2.8/5
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Vacation Homes in Osceola

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