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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
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Grhrfd1469 - Champions Gate Resort - 9 Bed 5 Baths House

Vacation Home

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Osceola
Grhrfd1469 - 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 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This family-friendly vacation home is 12.8 mi (20.7 km) from Old Town and 13.4 mi (21.6 km) from Walt Disney World® Resort.

Grhrfd1469 - 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.

Grhrfd1469 - 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Others

Disney Getaway: Pool, Spa, Games, Great Locale

Vacation Home

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Osceola
Disney Getaway: Pool, Spa, Games, Great Locale Location
Located in Kissimmee, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.6 mi (13.9 km) from Walt Disney World® Resort and 10.4 mi (16.8 km) from Disney's Animal Kingdom® Theme Park.

Disney Getaway: Pool, Spa, Games, Great Locale Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Disney Getaway: Pool, Spa, Games, Great Locale 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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Beautiful 6bd Pool Gm Spa Hm Champions Gate-1660mv 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Beautiful 6bd Pool Gm Spa Hm Champions Gate-1660mv 6 Bedroom Home by RedAwning Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.4 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

Beautiful 6bd Pool Gm Spa Hm Champions Gate-1660mv 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. 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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Bedroom

Windsor at Westside IHR 3100

Vacation Home

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Osceola
Windsor at Westside IHR 3100 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 vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

Windsor at Westside IHR 3100 Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Windsor at Westside IHR 3100 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private furnished balcony/patio. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected.

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Exterior & Views

Beachy Retreat

Vacation Home

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Osceola
Beachy Retreat Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, a 4-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This vacation home is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.5 km) from Disney's Animal Kingdom® Theme Park.

Beachy Retreat Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Beachy Retreat Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. Digital television is provided for your entertainment. Conveniences include a separate sitting area and a microwave.

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4.0/5
Fully Booked
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Others

9069hs- The Retreat at Championsgate

Vacation Home

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Osceola
9069hs- The Retreat at Championsgate 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 golf vacation home is 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

9069hs- The Retreat at Championsgate 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 barbecue grills.

9069hs- The Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Encore 8BR Home, Pool & Spa, 10 Min to Disney

Vacation Home

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Osceola
Encore 8BR Home, Pool & Spa, 10 Min to Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 5.5 mi (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Encore 8BR Home, Pool & Spa, 10 Min to Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub.

Encore 8BR Home, Pool & Spa, 10 Min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Welcome to The Dream Getaway

Vacation Home

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Osceola
Welcome to The Dream Getaway Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This vacation home is 7.7 mi (12.4 km) from Walt Disney World® Resort and 10 mi (16 km) from ESPN Wide World of Sports Complex.

Welcome to The Dream Getaway 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.

Welcome to The Dream Getaway Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
Fully Booked
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Dazzling Home With Putting Green at Encore

Vacation Home

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Osceola
Dazzling Home With Putting Green at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.7 mi (12.3 km) from ESPN Wide World of Sports Complex.

Dazzling Home With Putting Green at Encore Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Dazzling Home With Putting Green at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

4 Bed 2245

Private Vacation Home

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Osceola
4 Bed 2245 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 (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

4 Bed 2245 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

4 Bed 2245 Rooms
Your vacation home features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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1.0/5
Fully Booked
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Others

Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning 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 vacation home is 11.7 mi (18.9 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning Facility and Service
This smoke-free vacation home offers a foosball table.

Champions Gate Near Disney Privacy In Back! 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment.

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Exterior & Views

Once Upon a Stay

Vacation Home

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Osceola
Once Upon a Stay Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 9.9 mi (15.9 km) from Disney Springs™ and 10.1 mi (16.2 km) from Walt Disney World® Resort.

Once Upon a Stay Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Once Upon a Stay 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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4.5/5
Fully Booked
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Bedroom

6BR 4BA Home in Windsor Hills by CV-2520

Vacation Home

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Osceola
6BR 4BA Home in Windsor Hills by CV-2520 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 5.8 mi (9.4 km) from ESPN Wide World of Sports Complex and 6.4 mi (10.3 km) from Old Town.

6BR 4BA Home in Windsor Hills by CV-2520 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

6BR 4BA Home in Windsor Hills by CV-2520 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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4929GC Townhouse 4 Beds & 3 Baths with Private Pool

Vacation Home

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Osceola
Fully Booked
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Others

Grhscd9162 - Champions Gate Resort - 8 Bed 5 Baths House

Vacation Home

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Osceola
Grhscd9162 - Champions Gate Resort - 8 Bed 5 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.

Grhscd9162 - Champions Gate Resort - 8 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhscd9162 - Champions Gate Resort - 8 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
Let's check on other dates!
Exterior & Views

4BR 3BA Home in Rolling Hiils by CV-7901

Vacation Home

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Osceola
4BR 3BA Home in Rolling Hiils by CV-7901 Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6.2 mi (9.9 km) from Old Town.

4BR 3BA Home in Rolling Hiils by CV-7901 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

4BR 3BA Home in Rolling Hiils by CV-7901 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 is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Fully Booked
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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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Exterior & Views

Grhed1510 - Reunion Resort - 4 Bed 4 Baths House

Vacation Home

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Osceola
Grhed1510 - Reunion Resort - 4 Bed 4 Baths House Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 2-minute drive from Reunion Resort Golf Course and 7 minutes from ChampionsGate Golf Club. This family-friendly vacation home is 7.7 mi (12.4 km) from Walt Disney World® Resort and 9.3 mi (15 km) from Disney's Animal Kingdom® Theme Park.

Grhed1510 - Reunion Resort - 4 Bed 4 Baths House Facility and Service
Dip into one of the 8 outdoor pools or 2 hot tubs and enjoy other recreational amenities, which include a complimentary water park. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhed1510 - Reunion Resort - 4 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 with cable programming is available for your entertainment, and a video-game console is also provided.

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

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Sport & Beauty

Grhcup8936 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhcup8936 - Paradise Palms Resort - 5 Bed 4 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 8.1 mi (13 km) from Disney's Animal Kingdom® Theme Park and 8.9 mi (14.4 km) from ESPN Wide World of Sports Complex.

Grhcup8936 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcup8936 - Paradise Palms Resort - 5 Bed 4 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.

See details
Fully Booked
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Exterior & Views

Brand New Storey Lake Resort With Water Slides 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Brand New Storey Lake Resort With Water Slides 4 Bedroom Townhouse by RedAwning Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 6 mi (9.6 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

Brand New Storey Lake Resort With Water Slides 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your air-conditioned villa. Complimentary wireless internet access is available to keep you connected.

See details
Fully Booked
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Vacation Homes in Osceola

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