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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
Others

Joyful 8Bd Single Family w Pool @Champions Gate 9262

Private Vacation Home

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Osceola
Joyful 8Bd Single Family w Pool @Champions Gate 9262 Location
With a stay at this vacation home in Four Corners, 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 13.1 mi (21.1 km) from ESPN Wide World of Sports Complex.

Joyful 8Bd Single Family w Pool @Champions Gate 9262 Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and a lazy river. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Joyful 8Bd Single Family w Pool @Champions Gate 9262 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a DVD player and cable programming provide entertainment. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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4.0/5
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Exterior & Views

4BR Pool Home Emerald Island by SHV-2659

Private Vacation Home

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Osceola
4BR Pool Home Emerald Island by SHV-2659 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 7.3 mi (11.8 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

4BR Pool Home Emerald Island by SHV-2659 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, and you can also request a crib/infant bed (complimentary).

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Windsor at Westside Resort 5 Bedroom Private Pool+Spa Home 5 Home

Vacation Home

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Osceola
Windsor at Westside Resort 5 Bedroom Private Pool+Spa Home 5 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 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.4 km) from ESPN Wide World of Sports Complex.

Windsor at Westside Resort 5 Bedroom Private Pool+Spa Home 5 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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Others

Beautiful 8 Bed Home In Champions Gate-303oc 8 Bedroom Home by RedAwning

Vacation Home

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Osceola
Beautiful 8 Bed Home In Champions Gate-303oc 8 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.3 mi (19.8 km) from Walt Disney World® Resort and 12.4 mi (19.9 km) from Old Town.

Beautiful 8 Bed Home In Champions Gate-303oc 8 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC

Vacation Home

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Osceola
Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC Location
With a stay at this vacation home in Kissimmee (Trafalgar Village), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11 mi (17.7 km) from Old Town and 13.2 mi (21.3 km) from Orlando Vineland Premium Outlets.

Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Water View Retreat With Lanai, Heated Pool, Pool Spa, Game Room, & AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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1.0/5
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Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse

Vacation Home

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Osceola
Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This vacation home is 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom Townhouse Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center.

Sunny Paradise Retreat At Paradise Palms By Shine Villas 4 Bedroom 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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Family Home 9 BR 8 Min to Disney!

Vacation Home

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Osceola
Family Home 9 BR 8 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 6.2 mi (9.9 km) from Disney Springs™ and 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex.

Family Home 9 BR 8 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 an arcade/game room.

Family Home 9 BR 8 Min to Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Shd4720

Vacation Home

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Osceola
Shd4720 Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 6 mi (9.6 km) from Disney Springs™ and 6.6 mi (10.7 km) from Walt Disney World® Resort.

Shd4720 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a desk and a microwave.

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Sport & Beauty

Formosa Gardens Homes by Atlas VH

Vacation Home

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Osceola
Formosa Gardens Homes by Atlas VH Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This luxury vacation home is 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex and 6.2 mi (10 km) from Old Town.

Formosa Gardens Homes by Atlas VH Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

Formosa Gardens Homes by Atlas VH Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wired and wireless internet access is available. Conveniences include a microwave and a coffee/tea maker.

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Exterior & Views

Storey Lake 9BR Wonderland Home 2852

Private Vacation Home

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Osceola
Storey Lake 9BR Wonderland Home 2852 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 6.3 mi (10.1 km) from Disney Springs™ and 7.3 mi (11.7 km) from Walt Disney World® Resort.

Storey Lake 9BR Wonderland Home 2852 Facility and Service
Take advantage of recreation opportunities such as an outdoor tennis court, or other amenities including complimentary wireless internet access and an arcade/game room.

Storey Lake 9BR Wonderland Home 2852 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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Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508

Vacation Home

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Osceola
Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508 Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of Old Town and ChampionsGate Golf Club. This family-friendly vacation home is 11.8 mi (19 km) from ESPN Wide World of Sports Complex and 11.9 mi (19.1 km) from Walt Disney World® Resort.

Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508 Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and a lazy river. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a DVD player and cable programming provide entertainment. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

See details
4.0/5
Fully Booked
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Stunning 5Bd W/ Pool Close To Disney At Champions Gate 8956

Vacation Home

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Osceola
Stunning 5Bd W/ Pool Close To Disney At Champions Gate 8956 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.5 mi (20.1 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

Stunning 5Bd W/ Pool Close To Disney At Champions Gate 8956 Rooms
Make yourself comfortable in your vacation home.

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5.0/5
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Bedroom

19 Guest Home w Pool Hot Tub Cinema BBQ

Vacation Home

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Osceola
19 Guest Home w Pool Hot Tub Cinema BBQ 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 family-friendly vacation home is 9.1 mi (14.6 km) from Disney Springs™ and 10.1 mi (16.2 km) from Walt Disney World® Resort.

19 Guest Home w Pool Hot Tub Cinema BBQ Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and gas grills.

19 Guest Home w Pool Hot Tub Cinema BBQ 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.

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2.5/5
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Championsgate Resort 4 Bedroom Townhome with Pool 4 Townhouse

Vacation Home

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Osceola
Championsgate Resort 4 Bedroom Townhome with Pool 4 Townhouse Location
Located in Kissimmee, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 10.1 mi (16.2 km) from Walt Disney World® Resort and 12.3 mi (19.9 km) from Old Town.

Championsgate Resort 4 Bedroom Townhome with Pool 4 Townhouse 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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Bedroom

Themed 5BR Pool Home in Championsgate Close2disney

Vacation Home

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Osceola
Themed 5BR Pool Home in Championsgate Close2disney Location
Located in Four Corners, this vacation home is within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 12 mi (19.3 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

Themed 5BR Pool Home in Championsgate Close2disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Themed 5BR Pool Home in Championsgate Close2disney 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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4.5/5
Fully Booked
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Others

Grhmvd1596 - Champions Gate Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhmvd1596 - Champions Gate Resort - 5 Bed 4 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 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Grhmvd1596 - Champions Gate Resort - 5 Bed 4 Baths Townhouse 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.

Grhmvd1596 - Champions Gate 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
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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Near Theme Parks, fun Filled Home With Harry Potter Bedroom, & Private Pool

Vacation Home

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Osceola
Near Theme Parks, fun Filled Home With Harry Potter Bedroom, & Private Pool 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 Reunion Resort Golf Course. This vacation home is 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Animal Kingdom® Theme Park.

Near Theme Parks, fun Filled Home With Harry Potter Bedroom, & Private Pool 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.

Near Theme Parks, fun Filled Home With Harry Potter Bedroom, & Private Pool 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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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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Exterior & Views

421 NP - Exquisite Retreat at Encore Resort

Vacation Home

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Osceola
421 NP - Exquisite Retreat at Encore 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 vacation home is 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

421 NP - Exquisite Retreat at Encore Resort Facility and Service
Take advantage of recreation opportunities including an indoor pool and a fitness center. Additional features at this vacation home include gas grills and complimentary use of a nearby fitness facility.

421 NP - Exquisite Retreat at Encore Resort Rooms
Make yourself comfortable in this vacation home, featuring a kitchenette with a full-sized refrigerator/freezer and a dishwasher. Complimentary wireless internet access is available to keep you connected.

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Bedroom

1559pw NON Renting 8/15/21the Retreat at Championsgate

Vacation Home

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Osceola
1559pw NON Renting 8/15/21the 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 11.1 mi (17.9 km) from Old Town and 11.9 mi (19.2 km) from ESPN Wide World of Sports Complex.

1559pw NON Renting 8/15/21the Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1559pw NON Renting 8/15/21the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Vacation Homes in Osceola

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