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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
Room

Family 3BR Home in Lucaya Resort

Vacation Home

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Osceola
Family 3BR Home in Lucaya Resort Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 5.6 mi (9.1 km) from Walt Disney World® Resort.

Family 3BR Home in Lucaya Resort Rooms
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Two-story, Dog-friendly gem Near Theme Parks With Pool, Central AC & On-site gym

Vacation Home

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Osceola
Two-story, Dog-friendly gem Near Theme Parks With Pool, Central AC & On-site gym 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 7.1 mi (11.4 km) from Disney's Animal Kingdom® Theme Park and 8.1 mi (13.1 km) from ESPN Wide World of Sports Complex.

Two-story, Dog-friendly gem Near Theme Parks With Pool, Central AC & On-site gym Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and a fitness center.

Two-story, Dog-friendly gem Near Theme Parks With Pool, Central AC & On-site gym Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor Hills Resort 6 Bedroom Pool+Spa Home 6 Home

Vacation Home

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Osceola
Windsor Hills Resort 6 Bedroom Pool+Spa Home 6 Home Location
With a stay at this vacation home in Kissimmee (Windsor Hills), 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 (9.1 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.6 km) from Old Town.

Windsor Hills Resort 6 Bedroom Pool+Spa Home 6 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 Townhouse Next to Disney Parks 04

Vacation Home

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Osceola
Beautiful Townhouse Next to Disney Parks 04 Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This cottage is 7.1 mi (11.4 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.3 km) from Old Town.

Beautiful Townhouse Next to Disney Parks 04 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Beautiful Townhouse Next to Disney Parks 04 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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4.0/5
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Bright Luxe At Championsgate

Vacation Home

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Osceola
Bright Luxe 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 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Bright Luxe At Championsgate Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool. Conveniences include a separate sitting area and a washer/dryer.

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Sport & Beauty

Paradise Palms- 4 Bed Townhome W/splashpool-3202pp 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Paradise Palms- 4 Bed Townhome W/splashpool-3202pp 4 Bedroom Townhouse by RedAwning Location
With a stay at this villa in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly villa is 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Paradise Palms- 4 Bed Townhome W/splashpool-3202pp 4 Bedroom Townhouse by RedAwning Facility and Service
Enjoy recreational amenities such as an outdoor tennis court and a fitness center.

Paradise Palms- 4 Bed Townhome W/splashpool-3202pp 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator 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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Stylish Home With Galactic Themed Bedroom at Encore

Vacation Home

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Osceola
Stylish Home With Galactic Themed Bedroom 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 ChampionsGate Golf Club. This vacation home is 5.5 mi (8.9 km) from Walt Disney World® Resort and 7.8 mi (12.5 km) from ESPN Wide World of Sports Complex.

Stylish Home With Galactic Themed Bedroom at Encore Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Stylish Home With Galactic Themed Bedroom at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

3br, 2.5ba Townhome W/ Lake View, Sunny Rear Yard 3 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
3br, 2.5ba Townhome W/ Lake View, Sunny Rear Yard 3 Bedroom Townhouse 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 8.9 mi (14.3 km) from Disney Springs™ and 9.2 mi (14.8 km) from Walt Disney World® Resort.

3br, 2.5ba Townhome W/ Lake View, Sunny Rear Yard 3 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Reunion Retreat 3 Bedroom Home by RedAwning

Vacation Home

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Osceola
Reunion Retreat 3 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 2-minute drive from Reunion Resort Golf Course and 6 minutes from ChampionsGate Golf Club. This vacation home is 8 mi (12.9 km) from Walt Disney World® Resort and 9.7 mi (15.6 km) from Old Town.

Reunion Retreat 3 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your individually decorated 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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Others

Spacious 5bd Pool Th, Champions Gate-1610mvd 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Spacious 5bd Pool Th, Champions Gate-1610mvd 5 Bedroom Townhouse by RedAwning Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Spacious 5bd Pool Th, Champions Gate-1610mvd 5 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Bedroom

Veranda Palms IHR 3084

Private Vacation Home

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Osceola
Veranda Palms IHR 3084 Location
Located in Kissimmee (Veranda Palms), this vacation home is within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This spa vacation home is 6.7 mi (10.9 km) from Disney Springs™ and 7.8 mi (12.5 km) from Walt Disney World® Resort.

Veranda Palms IHR 3084 Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

Veranda Palms IHR 3084 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony or patio. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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View from room

Townhouse 4 Bedrooms 5 Min to Disney!

Vacation Home

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Osceola
Townhouse 4 Bedrooms 5 Min to Disney! Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 5-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This vacation home is 5 mi (8.1 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.5 km) from Old Town.

Townhouse 4 Bedrooms 5 Min to Disney! Facility and Service
Don't miss out on recreational opportunities including a hot tub and a fitness center. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Townhouse 4 Bedrooms 5 Min to Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Cheerful Estate With Water Park Views in Encore

Vacation Home

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Osceola
Cheerful Estate With Water Park Views 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 family-friendly 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.

Cheerful Estate With Water Park Views in Encore Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Cheerful Estate With Water Park Views in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Disney's Family Retreat

Vacation Home

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Osceola
Disney's Family Retreat Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 9.8 mi (15.8 km) from ESPN Wide World of Sports Complex and 10 mi (16.1 km) from Disney's Animal Kingdom® Theme Park.

Disney's Family Retreat Facility and Service
Enjoy recreation amenities such as an indoor pool or take in the view from a garden.

Disney's Family Retreat Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private patio. 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.

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Exterior & Views

720dsd-the Retreat at Championsgate

Vacation Home

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Osceola
720dsd-the Retreat at Championsgate Location
With a stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This golf vacation home is 12.4 mi (20 km) from Old Town and 12.9 mi (20.8 km) from ESPN Wide World of Sports Complex.

720dsd-the Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

720dsd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Bright Home With Private Pool, Washer/dryer and Internet

Vacation Home

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Osceola
Bright Home With Private Pool, Washer/dryer and Internet 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 8.3 mi (13.3 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Bright Home With Private Pool, Washer/dryer and Internet Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Bright Home With Private Pool, Washer/dryer and Internet Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

House W/pool And Jacuzzi In Paradise Palms-3151pp 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
House W/pool And Jacuzzi In Paradise Palms-3151pp 6 Bedroom Home by RedAwning 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 8.5 mi (13.6 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

House W/pool And Jacuzzi In Paradise Palms-3151pp 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. 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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Exterior & Views

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Private Vacation Home

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Osceola
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131 Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.8 mi (9.3 km) from Disney Springs™ and 6.8 mi (10.9 km) from Walt Disney World® Resort.

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131 Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131 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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4.5/5
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Windsor Hills 3 Bedroom Private Pool Townhome 3 Townhouse

Vacation Home

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Osceola
Windsor Hills 3 Bedroom Private Pool Townhome 3 Townhouse 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 Old Town. This vacation home is 6 mi (9.6 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.9 km) from Disney's Hollywood Studios®.

Windsor Hills 3 Bedroom Private Pool Townhome 3 Townhouse 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

Sunshine Getaway in Heart of Kissimmee

Vacation Home

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Osceola
Sunshine Getaway in Heart of Kissimmee Location
Located in Kissimmee, Sunshine Getaway in Heart of Kissimmee is in the entertainment district, within a 10-minute drive of Shingle Creek Regional Park and Green Meadows Petting Farm. This vacation home is 12.3 mi (19.9 km) from Old Town and 14.6 mi (23.4 km) from Orlando Vineland Premium Outlets.

Sunshine Getaway in Heart of Kissimmee Rooms
Make yourself at home in one of the 3 guestrooms, featuring kitchens with refrigerators and ovens. Rooms have private furnished balconies or patios. Complimentary wireless internet access is available to keep you connected. Conveniences include desks and microwaves.

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Vacation Homes in Osceola

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