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Vacation Homes in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
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Cg1564 - 4BR House With Pool Near Disney Area

Vacation Home

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Osceola
Cg1564 - 4BR House With Pool Near Disney Area Location
Located in Four Corners, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This cottage is 11.6 mi (18.6 km) from Old Town and 12.3 mi (19.9 km) from ESPN Wide World of Sports Complex.

Cg1564 - 4BR House With Pool Near Disney Area Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Cg1564 - 4BR House With Pool Near Disney Area 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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House w/ Pool, Game Room, and 6 Suites

Vacation Home

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Osceola
House w/ Pool, Game Room, and 6 Suites Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This villa is 7.3 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.5 km) from Disney's Hollywood Studios®.

House w/ Pool, Game Room, and 6 Suites Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

House w/ Pool, Game Room, and 6 Suites Rooms
Make yourself comfortable in your villa. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a separate bathtub and shower and complimentary toiletries.

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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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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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Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis

Vacation Home

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Osceola
Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis 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 11.6 mi (18.7 km) from Old Town and 13.8 mi (22.3 km) from Orlando Vineland Premium Outlets.

Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Family-friendly Home With Pool & Movie Theater

Vacation Home

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Osceola
Family-friendly Home With Pool & Movie Theater 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 vacation home is 12.1 mi (19.4 km) from Old Town and 12.6 mi (20.4 km) from Walt Disney World® Resort.

Family-friendly Home With Pool & Movie Theater Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Family-friendly Home With Pool & Movie Theater 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

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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Bedroom

Cozy Home Storey Lake Resort Pool Spa Near Disney

Vacation Home

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Osceola
Cozy Home Storey Lake Resort Pool Spa Near Disney 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 6.2 mi (10 km) from Disney Springs™ and 7.2 mi (11.5 km) from ESPN Wide World of Sports Complex.

Cozy Home Storey Lake Resort Pool Spa Near Disney 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.

Cozy Home Storey Lake Resort 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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Bedroom

Upstay - Theater Games Sleeps 16 Pool

Vacation Home

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Osceola
Upstay - Theater Games Sleeps 16 Pool 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 (16.4 km) from ESPN Wide World of Sports Complex and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Upstay - Theater Games Sleeps 16 Pool Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an indoor pool.

Upstay - Theater Games Sleeps 16 Pool Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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4.0/5
Fully Booked
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Sl3111 - 4BR House With Pool Near Disney Parks

Vacation Home

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Osceola
Sl3111 - 4BR House With Pool Near Disney Parks 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 (9.7 km) from Disney Springs™ and 7 mi (11.2 km) from Walt Disney World® Resort.

Sl3111 - 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.

Sl3111 - 4BR House With Pool Near Disney Parks 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.

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Exterior & Views

8167 sun Palm Drive

Private Vacation Home

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Osceola
8167 sun Palm Drive 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 (13.6 km) from Disney's Hollywood Studios® and 9.4 mi (15.2 km) from Disney's Animal Kingdom® Theme Park.

8167 sun Palm Drive Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an indoor pool, and an outdoor tennis court.

8167 sun Palm Drive 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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Charming Dog-friendly Home With Pool, hot Tub, Fitness Center, Patio, & Kitchen

Vacation Home

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Osceola
Charming Dog-friendly Home With Pool, hot Tub, Fitness Center, Patio, & Kitchen Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be a 4-minute drive from ChampionsGate Golf Club and 10 minutes from Reunion Resort Golf Course. This vacation home is 9.4 mi (15.1 km) from Old Town and 9.9 mi (15.9 km) from ESPN Wide World of Sports Complex.

Charming Dog-friendly Home With Pool, hot Tub, Fitness Center, Patio, & Kitchen Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts

Vacation Home

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Osceola
Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts 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 mi (12.8 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts Facility and Service
Enjoy a range of recreational amenities, including a hot tub, an outdoor tennis court, and a sauna. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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5-bedroom House in Championsgate With Private Pool

Vacation Home

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Osceola
5-bedroom House in Championsgate With Private Pool Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This villa is 12.4 mi (19.9 km) from Walt Disney World® Resort and 12.4 mi (20 km) from Old Town.

5-bedroom House in Championsgate With Private Pool Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This villa also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

5-bedroom House in Championsgate With Private Pool Rooms
Your villa features a Smart TV. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a desk and a separate sitting area, and you can also request a crib/infant bed (complimentary).

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Beautiful Tranquil Relaxing Home With Private Pool 4 Bedroom Townhouse

Vacation Home

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Osceola
Beautiful Tranquil Relaxing Home With Private Pool 4 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Beautiful Tranquil Relaxing Home With Private Pool 4 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

Family Fun: Pool, Spa & Theme Parks Nearby

Vacation Home

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Osceola
Family Fun: Pool, Spa & Theme Parks Nearby 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.

Family Fun: Pool, Spa & Theme Parks Nearby 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 Fun: Pool, Spa & Theme Parks Nearby 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.

See details
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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
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Grhbuc2979 - Paradise Palms Resort - 5 Bed 5 Baths House

Vacation Home

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Osceola
Grhbuc2979 - Paradise Palms Resort - 5 Bed 5 Baths House 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 (13.6 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Grhbuc2979 - Paradise Palms Resort - 5 Bed 5 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 3 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhbuc2979 - Paradise Palms Resort - 5 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
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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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.

See details
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Vacation Homes in Osceola

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