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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
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Windsor Westside Resort 7 Bedroom Home with Game Room 7 Home

Vacation Home

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Osceola
Windsor Westside Resort 7 Bedroom Home with Game Room 7 Home 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 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Windsor Westside Resort 7 Bedroom Home with Game Room 7 Home 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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Sport & Beauty

4677 Cumbrian Lakes

Vacation Home

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Osceola
4677 Cumbrian Lakes Location
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 10.3 mi (16.5 km) from Disney Springs™ and 10.6 mi (17 km) from Walt Disney World® Resort.

4677 Cumbrian Lakes Rooms
Make yourself comfortable in this vacation home, which features a private pool and a Smart TV. Wireless internet access (surcharge) is available to keep you connected.

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Room

5 Bed 4.5 Bath Townhouse W/ Pool Solara 2307dist 5 Bedroom Townhouse

Vacation Home

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Osceola
5 Bed 4.5 Bath Townhouse W/ Pool Solara 2307dist 5 Bedroom Townhouse 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 (13.8 km) from Walt Disney World® Resort and 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park.

5 Bed 4.5 Bath Townhouse W/ Pool Solara 2307dist 5 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Room

Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney

Vacation Home

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Osceola
Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.6 mi (13.8 km) from Walt Disney World® Resort and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near 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.

Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Oi2836 - 4BR House With Pool Near Disney World

Private Vacation Home

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Osceola
Oi2836 - 4BR House With Pool Near Disney World Location
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 6 mi (9.7 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Oi2836 - 4BR House With Pool Near Disney World Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Oi2836 - 4BR House With Pool Near Disney World Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private patio. Conveniences include a microwave and a washer/dryer.

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Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis

Vacation Home

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Osceola
Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 6.1 mi (9.8 km) from Old Town and 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex.

Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis Facility and Service
Take advantage of recreation opportunities including a hot tub and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and barbecue grills.

Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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5 Bed With Private Splash Pool! 5 Bedroom Townhouse

Vacation Home

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Osceola
5 Bed With Private Splash Pool! 5 Bedroom Townhouse 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 (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

5 Bed With Private Splash Pool! 5 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Room

Ultimate Resort Retreat Stunning 6-bedroom Haven

Vacation Home

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Osceola
Ultimate Resort Retreat Stunning 6-bedroom Haven 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 (16.7 km) from Disney's Animal Kingdom® Theme Park.

Ultimate Resort Retreat Stunning 6-bedroom Haven Facility and Service
Take in the views from a garden.

Ultimate Resort Retreat Stunning 6-bedroom Haven Rooms
Make yourself comfortable in your vacation home.

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4.0/5
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Water park

Stunning Game Room & Pool Jacuzzi Storey Lake 2799

Vacation Home

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Osceola
Stunning Game Room & Pool Jacuzzi Storey Lake 2799 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 6.6 mi (10.6 km) from Disney Springs™ and 7.6 mi (12.2 km) from Walt Disney World® Resort.

Stunning Game Room & Pool Jacuzzi Storey Lake 2799 Rooms
Make yourself comfortable in your vacation home.

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4.9/5
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Sv2925 - 4BR House With Pool Near Disney Parks

Vacation Home

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Osceola
Sv2925 - 4BR House With Pool Near Disney Parks Location
With a stay at this cottage in Kissimmee (Sunset Lakes), you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This cottage is 7.4 mi (11.9 km) from Old Town and 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex.

Sv2925 - 4BR House With Pool Near Disney Parks Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sv2925 - 4BR House With Pool Near Disney Parks Rooms
Make yourself comfortable in this individually decorated cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a washer/dryer.

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Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis

Vacation Home

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Osceola
Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 2-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This vacation home is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Old Town.

Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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12BR house with game room near Disney area

Vacation Home

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Osceola
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Lobby

Huge Home, Private Pool Sleeps 16

Vacation Home

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Osceola
Huge Home, Private Pool Sleeps 16 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 11.2 mi (18.1 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

Huge Home, Private Pool Sleeps 16 Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Huge Home, Private Pool Sleeps 16 Rooms
Make yourself comfortable in your individually decorated vacation home.

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Dog-friendly Retreat With hot Tub, Outdoor Pool, & Tennis Court - Great Location

Vacation Home

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Osceola
Dog-friendly Retreat With hot Tub, Outdoor Pool, & Tennis Court - Great Location 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 7.5 mi (12 km) from Disney Springs™ and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Dog-friendly Retreat With hot Tub, Outdoor Pool, & Tennis Court - Great Location Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Blue Crush House in Kissimmee With Pool, hot Tub, and Tennis Access

Vacation Home

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Osceola
Blue Crush House in Kissimmee With Pool, hot Tub, and Tennis Access Location
When you stay at this condo in Kissimmee, you'll be near the beach, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 6 mi (9.6 km) from Disney Springs™ and 6.3 mi (10.1 km) from Walt Disney World® Resort.

Blue Crush House in Kissimmee With Pool, hot Tub, and Tennis Access Facility and Service
Take advantage of recreational opportunities offered, including an outdoor tennis court, a sauna, and a fitness center. Additional features at this condo include complimentary wireless internet access and barbecue grills.

Blue Crush House in Kissimmee With Pool, hot Tub, and Tennis Access Rooms
Make yourself comfortable in your individually decorated condo. The bathroom has a bathtub or shower.

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Sport & Beauty

3097 Pequod Place

Private Vacation Home

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Osceola
3097 Pequod Place 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 5.9 mi (9.5 km) from Disney Springs™ and 6.9 mi (11.1 km) from Walt Disney World® Resort.

3097 Pequod Place Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Room

Comfy Vacation Home @solara!

Vacation Home

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Osceola
Comfy Vacation Home @solara! 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 ChampionsGate Golf Club. This vacation home is 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Comfy Vacation Home @solara! 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 barbecue grills.

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

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Exterior & Views

1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning 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 12.8 mi (20.6 km) from Old Town and 13.4 mi (21.5 km) from Walt Disney World® Resort.

1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including barbecue grills.

1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. There's a private patio. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Exterior & Views

Gorgeous Family Friendly 5 Bd w/ Pool Close to Disney @ Storey Lake 2767

Private Vacation Home

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Osceola
Gorgeous Family Friendly 5 Bd w/ Pool Close to Disney @ Storey Lake 2767 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 family-friendly vacation home is 6.6 mi (10.7 km) from Disney Springs™ and 7.7 mi (12.3 km) from Walt Disney World® Resort.

Gorgeous Family Friendly 5 Bd w/ Pool Close to Disney @ Storey Lake 2767 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Gorgeous Family Friendly 5 Bd w/ Pool Close to Disney @ Storey Lake 2767 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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2.0/5
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Others

Family-friendly House w/ Resort Pool & Splash Park

Vacation Home

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Osceola
Family-friendly House w/ Resort Pool & Splash Park 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 6.8 mi (11 km) from Walt Disney World® Resort and 8.3 mi (13.4 km) from Old Town.

Family-friendly House w/ Resort Pool & Splash Park Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Family-friendly House w/ Resort Pool & Splash Park 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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Vacation Homes in Osceola

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