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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Mvd1441 6 Bedroom Home

Vacation Home

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Osceola
Mvd1441 6 Bedroom Home 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 (18.8 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

Mvd1441 6 Bedroom 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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Bedroom

8802 Macapa Drive

Private Vacation Home

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Osceola
8802 Macapa Drive Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This family-friendly vacation home is 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park and 11.6 mi (18.7 km) from Old Town.

8802 Macapa Drive Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

8802 Macapa Drive Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a dishwasher. Complimentary wireless internet access is available to keep you connected.

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Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi

Vacation Home

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Osceola
Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 4.9 mi (7.8 km) from ESPN Wide World of Sports Complex and 5.7 mi (9.2 km) from Disney's Hollywood Studios®.

Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi Facility and Service
Be sure to enjoy recreational amenities including an outdoor tennis court and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Bright, Centrally-located Getaway With a Pool, Clubhouse, & Fast Wifi 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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Room

8904-TropicalHaven

Vacation Home

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Osceola
8904-TropicalHaven 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 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

8904-TropicalHaven Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

8904-TropicalHaven Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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West Lucaya Village 4 Bedroom Townhome 4 Townhouse

Vacation Home

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Osceola
West Lucaya Village 4 Bedroom Townhome 4 Townhouse 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 Disney's Animal Kingdom® Theme Park and 8.6 mi (13.8 km) from ESPN Wide World of Sports Complex.

West Lucaya Village 4 Bedroom Townhome 4 Townhouse 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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Bright Home With Game Room Theater at Reunion

Vacation Home

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Osceola
Bright Home With Game Room Theater at Reunion 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 Mystic Dunes Golf Club. This vacation home is 7.4 mi (11.9 km) from Walt Disney World® Resort and 9.4 mi (15.2 km) from Old Town.

Bright Home With Game Room Theater at Reunion Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

Bright Home With Game Room Theater at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Luxury Storey Lake Retreat - Spacious Disney-near

Vacation Home

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Osceola
Luxury Storey Lake Retreat - Spacious Disney-near 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 (9.8 km) from Disney Springs™ and 7 mi (11.3 km) from Walt Disney World® Resort.

Luxury Storey Lake Retreat - Spacious Disney-near Facility and Service
Take in the views from a garden and make use of amenities such as barbecue grills.

Luxury Storey Lake Retreat - Spacious Disney-near Rooms
Make yourself comfortable in your vacation home.

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Room

Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks

Vacation Home

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Osceola
Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks 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 7.1 mi (11.4 km) from Disney Springs™ and 8.1 mi (13 km) from ESPN Wide World of Sports Complex.

Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Bright Modern Home @storey Lake

Vacation Home

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Osceola
Bright Modern Home @storey Lake Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.4 mi (12 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

Bright Modern Home @storey Lake 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 an arcade/game room and barbecue grills.

Bright Modern Home @storey Lake Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Paradise Palms-4 Bedroom Townhome-3001PP 4 Townhouse by RedAwning

Vacation Home

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Osceola
Paradise Palms-4 Bedroom Townhome-3001PP 4 Townhouse 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 8.2 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.

Paradise Palms-4 Bedroom Townhome-3001PP 4 Townhouse 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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Room

Lovely Family Home 8-10 min to Disney

Vacation Home

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Osceola
Lovely Family Home 8-10 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 Old Town and Orlando Vineland Premium Outlets. This vacation home is 5.8 mi (9.4 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

Lovely Family Home 8-10 min to Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Lovely Family Home 8-10 min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Modern Abode With Private Pool and Spa in Encore

Vacation Home

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Osceola
Modern Abode With Private Pool and Spa in 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 vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 7.8 mi (12.6 km) from ESPN Wide World of Sports Complex.

Modern Abode With Private Pool and Spa in Encore Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Modern Abode With Private Pool and Spa in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Aster Cove

Vacation Home

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Osceola
Aster Cove Location
With a stay at this vacation home in Kissimmee (Crescent Lakes), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11.5 mi (18.5 km) from Old Town and 13.7 mi (22.1 km) from Orlando Vineland Premium Outlets.

Aster Cove Facility and Service
Enjoy recreational amenities such as an outdoor pool and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and a picnic area.

Aster Cove Rooms
Treat yourself to a stay in this individually furnished 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 digital programming is available for your entertainment. Conveniences include a desk and a separate sitting area, as well as a phone with free local calls.

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Room

Resort-style Living w Private Pool & Amenities

Vacation Home

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Osceola
Resort-style Living w Private Pool & Amenities Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, 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 10.7 mi (17.2 km) from Walt Disney World® Resort.

Resort-style Living w Private Pool & Amenities Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and a fitness center. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Resort-style Living w Private Pool & Amenities Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Lobby

Comfy Vacation Home, Private Pool!

Vacation Home

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Osceola
Comfy Vacation Home, Private Pool! 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 vacation home is 12.7 mi (20.4 km) from Old Town and 13.3 mi (21.3 km) from Walt Disney World® Resort.

Comfy Vacation Home, Private Pool! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Comfy Vacation Home, Private Pool! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Extraordinary Solara 7BR Private Pool/spa Near Disney

Vacation Home

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Osceola
Extraordinary Solara 7BR Private Pool/spa Near Disney 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 8.7 mi (14.1 km) from Walt Disney World® Resort and 10.5 mi (17 km) from Disney's Animal Kingdom® Theme Park.

Extraordinary Solara 7BR Private Pool/spa Near Disney Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Extraordinary Solara 7BR Private Pool/spa 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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Others

Hideaway Dream 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Hideaway Dream 6 Bedroom Home 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 9 mi (14.5 km) from Disney Springs™ and 9.3 mi (15 km) from Walt Disney World® Resort.

Hideaway Dream 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

4BR 3BA Home in Windsor Palms by CV-8112

Vacation Home

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Osceola
4BR 3BA Home in Windsor Palms by CV-8112 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 7 mi (11.3 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.6 km) from Old Town.

4BR 3BA Home in Windsor Palms by CV-8112 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 DVD player is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Others

Fv46473 - Paradise Palms - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Fv46473 - Paradise Palms - 4 Bed 3 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 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (14.9 km) from ESPN Wide World of Sports Complex.

Fv46473 - Paradise Palms - 4 Bed 3 Baths Townhome 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 gift shops/newsstands.

Fv46473 - Paradise Palms - 4 Bed 3 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 video-game console are provided for your entertainment.

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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Room

Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102

Vacation Home

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Osceola
Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102 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 6.1 mi (9.9 km) from Disney Springs™ and 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex.

Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Mickey Mouse Clubhouse 8min to Disneyworld Pool/spa Sleeps 20 St102 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Vacation Homes in Osceola

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