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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
Pool

Disney Decorated Home 8min to Disneyworld Pool/spa Sleeps 22 104

Vacation Home

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Osceola
Disney Decorated Home 8min to Disneyworld Pool/spa Sleeps 22 104 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 6.3 mi (10.1 km) from Disney Springs™ and 7.2 mi (11.7 km) from ESPN Wide World of Sports Complex.

Disney Decorated Home 8min to Disneyworld Pool/spa Sleeps 22 104 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Disney Decorated Home 8min to Disneyworld Pool/spa Sleeps 22 104 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

November Promo at Lucaya 3 Beds 2 Baths Id:59007

Vacation Home

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Osceola
November Promo at Lucaya 3 Beds 2 Baths Id:59007 Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Old Town and 10 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex.

November Promo at Lucaya 3 Beds 2 Baths Id:59007 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

November Promo at Lucaya 3 Beds 2 Baths Id:59007 Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Sport & Beauty

Indian Ridge- 4 Bedroom Pool Home- 2405IR 4 Home by RedAwning

Vacation Home

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Osceola
Indian Ridge- 4 Bedroom Pool Home- 2405IR 4 Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 10 minutes from Walt Disney World® Resort. This vacation home is 7.3 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Old Town.

Indian Ridge- 4 Bedroom Pool Home- 2405IR 4 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.

Indian Ridge- 4 Bedroom Pool Home- 2405IR 4 Home by RedAwning Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Others

8960 Majesty Palm rd

Private Vacation Home

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Osceola
8960 Majesty Palm rd 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 Animal Kingdom® Theme Park and 9.9 mi (15.9 km) from Disney's Hollywood Studios®.

8960 Majesty Palm rd Facility and Service
Enjoy a range of recreational amenities, including an indoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

8960 Majesty Palm rd Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washer/dryer.

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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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Others

Lakeside Community, Pools, and More!

Vacation Home

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Osceola
Lakeside Community, Pools, and More! Location
Located in Kissimmee (Buena Ventura Lakes), this vacation home is within a 5-minute drive of Houston Astros Spring Training and Silver Spurs Arena. This vacation home is 13.1 mi (21.1 km) from Old Town and 15.2 mi (24.4 km) from Disney Springs™.

Lakeside Community, Pools, and More! Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Lakeside Community, Pools, and More! Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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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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Sport & Beauty

Grhrfd1495 - Champions Gate Resort - 5 Bed 4 Baths House

Vacation Home

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Osceola
Grhrfd1495 - Champions Gate Resort - 5 Bed 4 Baths House Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This family-friendly vacation home is 12.7 mi (20.4 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

Grhrfd1495 - Champions Gate Resort - 5 Bed 4 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhrfd1495 - Champions Gate Resort - 5 Bed 4 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

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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Sport & Beauty

Grhcap8859 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhcap8859 - 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 (13.2 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.6 km) from ESPN Wide World of Sports Complex.

Grhcap8859 - 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.

Grhcap8859 - Paradise Palms 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
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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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.

See details
Fully Booked
Let's check on other dates!
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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Others

1517 Reunion

Vacation Home

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Osceola
1517 Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 6 mi (9.7 km) from Walt Disney World® Resort and 8.1 mi (13 km) from ESPN Wide World of Sports Complex.

1517 Reunion Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private hot tub. There's a private balcony. A kitchen is outfitted with a refrigerator, a microwave, and a dishwasher. Satellite programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Others

Lake View Cozy Home w/ Pool & Games Near Disney

Vacation Home

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Osceola
Lake View Cozy Home w/ Pool & Games Near Disney 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 6.9 mi (11.2 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Lake View Cozy Home w/ Pool & Games Near Disney Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Lake View Cozy Home w/ Pool & Games Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries.

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Pool

Family 5Bd Pool, Spa, Themed Rooms & GameRoom 7832

Vacation Home

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Osceola
Family 5Bd Pool, Spa, Themed Rooms & GameRoom 7832 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 9.9 mi (15.9 km) from Old Town and 10.7 mi (17.2 km) from ESPN Wide World of Sports Complex.

Family 5Bd Pool, Spa, Themed Rooms & GameRoom 7832 Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop.

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3.0/5
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Room

Modern Family 4BR Townhome Near Disney in Orlando

Vacation Home

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Osceola
Modern Family 4BR Townhome Near Disney in Orlando Location
With a stay at this vacation home in Kissimmee, you'll be a 1-minute drive from Old Town and 9 minutes from Walt Disney World® Resort. This vacation home is 4.6 mi (7.4 km) from ESPN Wide World of Sports Complex and 4.8 mi (7.7 km) from Disney's Hollywood Studios®.

Modern Family 4BR Townhome Near Disney in Orlando Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Modern Family 4BR Townhome Near Disney in Orlando Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

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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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.

See details
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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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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.

See details
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Vacation Homes in Osceola

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