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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
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2216 Wyndham Palms way

Private Vacation Home

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Osceola
2216 Wyndham Palms way 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 8.4 mi (13.5 km) from Disney's Hollywood Studios® and 9.4 mi (15.1 km) from Disney's Animal Kingdom® Theme Park.

2216 Wyndham Palms way Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an indoor pool, and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

2216 Wyndham Palms way Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a microwave and a coffee/tea maker.

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8523 Emerald Island

Vacation Home

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Osceola
8523 Emerald Island 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 7.3 mi (11.8 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

8523 Emerald Island Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

8523 Emerald Island Rooms
Make yourself comfortable in this vacation home, which features a private pool.

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7628recife

Vacation Home

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Osceola
7628recife 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 (8 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.4 km) from Disney's Hollywood Studios®.

7628recife Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including concierge services.

7628recife Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony.

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Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub

Vacation Home

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Osceola
Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub 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 Reunion Resort Golf Course. This vacation home is 11.9 mi (19.1 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 7 mi (11.3 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Ov2564 - Windsor Palms Resort - 4 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 a complimentary water park or a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome 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 programming along with a DVD player are 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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The Delightful Home 1132

Private Vacation Home

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Osceola
The Delightful Home 1132 Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 11.8 mi (19 km) from Old Town and 13.2 mi (21.2 km) from Walt Disney World® Resort.

The Delightful Home 1132 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

The Delightful Home 1132 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

Rum Runners and Margaritas

Vacation Home

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Osceola
Rum Runners and Margaritas Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 5.8 mi (9.3 km) from Old Town and 6.3 mi (10.2 km) from ESPN Wide World of Sports Complex.

Rum Runners and Margaritas Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub.

Rum Runners and Margaritas Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and an outdoor private hot tub. There's a private furnished balcony/patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 42-inch flat-screen television is provided, with digital programming available.

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2.0/5
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Bedroom

1525fd-the Retreat at Championsgate

Vacation Home

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Osceola
1525fd-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 11.2 mi (18 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

1525fd-the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1525fd-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Cw7713 Windsor Hills Resort Vacation Home

Vacation Home

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Osceola
Cw7713 Windsor Hills Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6 mi (9.6 km) from Old Town.

Cw7713 Windsor Hills Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Sport & Beauty

Huge 6-bed Emerald Is Resort- Elite Vacation Homes

Vacation Home

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Osceola
Huge 6-bed Emerald Is Resort- Elite Vacation Homes 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 7.1 mi (11.5 km) from Old Town and 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex.

Huge 6-bed Emerald Is Resort- Elite Vacation Homes Facility and Service
Take time to pamper yourself with a visit to the full-service spa. If you're looking for recreational opportunities, you'll find an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and a picnic area.

Huge 6-bed Emerald Is Resort- Elite Vacation Homes 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, a stovetop, and a microwave. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment.

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Grhcdw9151 - Champions Gate Resort - 9 Bed 5 Baths House

Vacation Home

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Osceola
Grhcdw9151 - 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 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

Grhcdw9151 - 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcdw9151 - 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.

See details
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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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1533cpc Solara Resort

Vacation Home

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Osceola
1533cpc Solara Resort 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 (16.5 km) from Disney's Animal Kingdom® Theme Park and 10.9 mi (17.5 km) from ESPN Wide World of Sports Complex.

1533cpc Solara Resort Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1533cpc Solara Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private furnished balcony/patio. A kitchen is outfitted with a refrigerator and a microwave. Cable programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Opulent Retreat With Pool & Fast Wifi Near Disney

Private Vacation Home

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Osceola
Opulent Retreat With Pool & Fast Wifi Near Disney Location
Located in Four Corners, this vacation home is within a 15-minute drive of Old Town and Reunion Resort Golf Course. This vacation home is 12 mi (19.3 km) from ESPN Wide World of Sports Complex and 12.1 mi (19.5 km) from Walt Disney World® Resort.

Opulent Retreat With Pool & Fast Wifi Near Disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Opulent Retreat With Pool & Fast Wifi 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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Exterior & Views

8911sydney

Vacation Home

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Osceola
8911sydney 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 family-friendly vacation home is 8.7 mi (14 km) from Walt Disney World® Resort and 10.5 mi (16.9 km) from Disney's Animal Kingdom® Theme Park.

8911sydney Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

8911sydney Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a private pool. A kitchen is outfitted with a refrigerator and a microwave. An LCD television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Regal Oaks Resort

Vacation Home

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Osceola
Regal Oaks Resort Location
With a stay at this vacation home in Kissimmee, you'll be a 1-minute drive from Old Town and 8 minutes from Walt Disney World® Resort. This vacation home is 4.3 mi (7 km) from ESPN Wide World of Sports Complex and 4.6 mi (7.4 km) from Disney's Hollywood Studios®.

Regal Oaks Resort Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and charcoal grills.

Regal Oaks Resort Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a Smart TV. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a coffee/tea maker and a ceiling fan.

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5.0/5
Fully Booked
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Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities

Vacation Home

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Osceola
Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities 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 Reunion Resort Golf Course. This vacation home is 12.1 mi (19.5 km) from Old Town and 12.9 mi (20.7 km) from ESPN Wide World of Sports Complex.

Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Sport & Beauty

Grhcap8858 - Paradise Palms Resort - 6 Bed 5 Baths House

Vacation Home

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Osceola
Grhcap8858 - Paradise Palms Resort - 6 Bed 5 Baths House Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.2 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.6 km) from ESPN Wide World of Sports Complex.

Grhcap8858 - Paradise Palms Resort - 6 Bed 5 Baths House 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.

Grhcap8858 - Paradise Palms Resort - 6 Bed 5 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
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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2767lkd-emerald Island Resort 7 Bedroom Home

Vacation Home

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Osceola
2767lkd-emerald Island Resort 7 Bedroom Home 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 7.2 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.4 km) from Disney's Hollywood Studios®.

2767lkd-emerald Island Resort 7 Bedroom Home Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. 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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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!
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Vacation Homes in Osceola

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