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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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Champions Gate, Pool, Themed Rooms

Vacation Home

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Osceola
Champions Gate, Pool, Themed Rooms Location
With a stay at Champions Gate, Pool, Themed Rooms in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This family-friendly vacation home is 12.3 mi (19.8 km) from Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

Champions Gate, Pool, Themed Rooms Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools.

Champions Gate, Pool, Themed Rooms Rooms
Make yourself at home in one of the 5 air-conditioned rooms featuring private pools. Rooms have private furnished patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected.

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5.0/5
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Sport & Beauty

Fs55568 - Oakwater Resort - 2 Bed 2 Baths Townhome

Vacation Home

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Osceola
Fs55568 - Oakwater Resort - 2 Bed 2 Baths Townhome Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 5.1 mi (8.2 km) from ESPN Wide World of Sports Complex and 5.6 mi (9 km) from Disney's Hollywood Studios®.

Fs55568 - Oakwater Resort - 2 Bed 2 Baths Townhome Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as an outdoor pool or a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Fs55568 - Oakwater Resort - 2 Bed 2 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. A flat-screen television with cable programming is available for your entertainment, and a DVD player is also provided. Conveniences include a microwave and a sofa bed.

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Marvelous 3 Bedroom Townhome w/Private Splash Pool Just Minutes from Disney and Mystic Dunes

Vacation Home

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Osceola
Marvelous 3 Bedroom Townhome w/Private Splash Pool Just Minutes from Disney and Mystic Dunes 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 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex and 8.3 mi (13.3 km) from Disney's Hollywood Studios®.

Marvelous 3 Bedroom Townhome w/Private Splash Pool Just Minutes from Disney and Mystic Dunes Rooms
Make yourself comfortable in your vacation home.

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Solara Resort 8 Bedroom Private Pool Home 8 Home

Vacation Home

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Osceola
Solara Resort 8 Bedroom Private Pool Home 8 Home 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 mi (17.7 km) from ESPN Wide World of Sports Complex.

Solara Resort 8 Bedroom Private Pool Home 8 Home 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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Exterior & Views

Fascinating Private Pool and Game-room, Near Disney!!

Vacation Home

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Osceola
Fascinating Private Pool and Game-room, Near Disney!! Location
With a stay at this vacation home in Kissimmee (Eagle Pointe South), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.7 mi (15.5 km) from Disney Springs™ and 9.8 mi (15.7 km) from ESPN Wide World of Sports Complex.

Fascinating Private Pool and Game-room, Near Disney!! Rooms
Your vacation home features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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Bedroom

Making Memories in West Lucaya Resort

Vacation Home

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Osceola
Making Memories in West Lucaya Resort 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 7.4 mi (11.9 km) from Disney's Animal Kingdom® Theme Park and 8.6 mi (13.8 km) from ESPN Wide World of Sports Complex.

Making Memories in West Lucaya Resort Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and complimentary use of a nearby fitness facility.

Making Memories in West Lucaya Resort 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 separate sitting area and a microwave.

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5.0/5
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Others

Family Fun: Pool, Spa, Games in Luxury Resort

Vacation Home

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Osceola
Family Fun: Pool, Spa, Games in Luxury Resort Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Island H2O Live! and ChampionsGate Golf Club. This vacation home is 9.2 mi (14.7 km) from Walt Disney World® Resort and 10.9 mi (17.6 km) from Disney's Animal Kingdom® Theme Park.

Family Fun: Pool, Spa, Games in Luxury Resort 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.

Family Fun: Pool, Spa, Games in Luxury Resort 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

4707 4-bdrm'slake Viewgames Roomoutdoor Spa!

Vacation Home

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Osceola
4707 4-bdrm'slake Viewgames Roomoutdoor Spa! Location
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This spa vacation home is 10.3 mi (16.6 km) from Disney Springs™ and 10.5 mi (16.9 km) from ESPN Wide World of Sports Complex.

4707 4-bdrm'slake Viewgames Roomoutdoor Spa! Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

4707 4-bdrm'slake Viewgames Roomoutdoor Spa! Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment.

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Others

4/3 Townhouse Near Disney!!

Vacation Home

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Osceola
4/3 Townhouse Near Disney!! Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.2 mi (11.6 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.3 km) from Old Town.

4/3 Townhouse Near Disney!! Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4/3 Townhouse Near Disney!! Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Cozy 3BR Townhome 5 Miles From Disney

Vacation Home

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Osceola
Cozy 3BR Townhome 5 Miles From Disney Location
Located in Kissimmee (Reunion), this vacation home is 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 8.3 mi (13.3 km) from ESPN Wide World of Sports Complex.

Cozy 3BR Townhome 5 Miles From Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Others

3 Bed 2819

Vacation Home

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Osceola
3 Bed 2819 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 6.1 mi (9.8 km) from Old Town and 6.2 mi (9.9 km) from ESPN Wide World of Sports Complex.

3 Bed 2819 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a stovetop and a dishwasher. There's a private patio. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment. Conveniences include a desk and a washer/dryer.

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Exterior & Views

Four Bedroom Pool Home - 1513 IOT - Vusa

Private Vacation Home

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Osceola
Four Bedroom Pool Home - 1513 IOT - Vusa Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World�� Resort. This vacation home is 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex and 7.3 mi (11.8 km) from Old Town.

Four Bedroom Pool Home - 1513 IOT - Vusa Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Four Bedroom Pool Home - 1513 IOT - Vusa Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a stovetop. Conveniences include a microwave and a washer/dryer.

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Exterior & Views

9 Bed Home Storey Lake 9 Bedroom Home by RedAwning

Vacation Home

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Osceola
9 Bed Home Storey Lake 9 Bedroom Home 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 6.1 mi (9.9 km) from Disney Springs™ and 7.2 mi (11.5 km) from Walt Disney World® Resort.

9 Bed Home Storey Lake 9 Bedroom Home 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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Exterior & Views

Econo Lodge Inn & Suites Maingate Central

Vacation Home

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Osceola
Econo Lodge Inn & Suites Maingate Central Location
When you stay at Econo Lodge Inn & Suites Maingate Central in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This hotel is 6.7 mi (10.8 km) from Disney Springs™ and 7.6 mi (12.2 km) from Walt Disney World® Resort.

Econo Lodge Inn & Suites Maingate Central Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and gift shops/newsstands. Additional features at this hotel include a picnic area, barbecue grills, and a vending machine.

Econo Lodge Inn & Suites Maingate Central Rooms
Make yourself at home in one of the 102 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include safes and desks, and housekeeping is provided daily.

Restaurant and Cafe
Grab a bite from the snack bar/deli serving guests of Econo Lodge Inn & Suites Maingate Central. A complimentary continental breakfast is served daily from 6:00 AM to 8:30 AM.

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4.0/5
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Sport & Beauty

Ov4256 - Paradise Palms - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Ov4256 - Paradise Palms - 5 Bed 4 Baths Townhome 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 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Ov4256 - Paradise Palms - 5 Bed 4 Baths Townhome 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.

Ov4256 - Paradise Palms - 5 Bed 4 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Conveniences include a washer/dryer and a ceiling fan.

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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Bedroom

6BR 4BA Home in Windsor Hills by CV-2534

Vacation Home

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Osceola
6BR 4BA Home in Windsor Hills by CV-2534 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 6.2 mi (10 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-2534 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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Exterior & Views

4882rc

Vacation Home

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Osceola
4882rc 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 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.

4882rc Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4882rc Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a flat-screen TV. A kitchen is outfitted with a refrigerator and a microwave. Complimentary wired and wireless internet access is available.

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Sport & Beauty

Emerald Island Resort

Private Vacation Home

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Osceola
Emerald Island Resort 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 family-friendly vacation home is 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.6 km) from Old Town.

Emerald Island Resort Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a terrace. Additional features at this vacation home include an arcade/game room and barbecue grills.

Emerald Island 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 an iron/ironing board.

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Others

Grhccr1368-302 - Reunion Resort - 3 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhccr1368-302 - Reunion Resort - 3 Bed 3 Baths Townhouse Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 1-minute drive from Reunion Resort Golf Course and 9 minutes from ChampionsGate Golf Club. This family-friendly vacation home is 6.9 mi (11.2 km) from Walt Disney World® Resort and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Grhccr1368-302 - Reunion Resort - 3 Bed 3 Baths Townhouse Facility and Service
Dip into one of the 8 outdoor pools 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.

Grhccr1368-302 - Reunion Resort - 3 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 with cable programming is available for your entertainment, and a video-game console is also provided. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Grhdog9045 - Champions Gate Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhdog9045 - 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 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Grhdog9045 - 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. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhdog9045 - Champions Gate 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
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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Vacation Homes in Osceola

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