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Hotels in Osceola

Osceola
Fri, 13 Nov 2026 - Sat, 14 Nov 2026 (1 night)
1 Room, 1 Adult, 0 Children
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Showing 5.000+ hotels in Osceola
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Callaghan Cantina 5 Bedroom Home by RedAwning

Osceola
Callaghan Cantina 5 Bedroom Home by RedAwning Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 5.8 mi (9.3 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.7 km) from Old Town.

Callaghan Cantina 5 Bedroom Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Callaghan Cantina 5 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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Tuscan Terrace

Osceola
Tuscan Terrace Location
With a stay at this condo in Four Corners (Champions Gate), you'll be a 5-minute drive from ChampionsGate Golf Club and 8 minutes from Reunion Resort Golf Course. This condo is 9 mi (14.5 km) from Walt Disney World® Resort and 9.6 mi (15.5 km) from Old Town.

Tuscan Terrace Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and barbecue grills.

Tuscan Terrace Rooms
Make yourself comfortable in your individually decorated condo. The bathroom has a bathtub or shower.

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Others

5BR Storey Lake Home With Private Pool

Osceola
5BR Storey Lake Home With Private Pool Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 5.5 mi (8.9 km) from Disney Springs™ and 6.6 mi (10.6 km) from Walt Disney World® Resort.

5BR Storey Lake Home With Private Pool Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and a picnic area.

5BR Storey Lake Home With Private Pool Rooms
Your villa features a flat-screen TV. There's a private furnished patio. 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.

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Interior

7613-8-bl-only 10 Minutes From Disney

Osceola
7613-8-bl-only 10 Minutes From Disney Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This cottage is 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.6 km) from Disney's Hollywood Studios®.

7613-8-bl-only 10 Minutes From Disney 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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Lakeview Spacious 12br Themed Home Game/pool/spa

Osceola
Lakeview Spacious 12br Themed Home Game/pool/spa 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 (14.4 km) from Disney Springs™ and 9.9 mi (16 km) from Walt Disney World® Resort.

Lakeview Spacious 12br Themed Home Game/pool/spa Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Lakeview Spacious 12br Themed Home Game/pool/spa 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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Grhcpr8972 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Osceola
Grhcpr8972 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Location
Located in Kissimmee, this vacation home is 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.

Grhcpr8972 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Dip into one of the 2 hot tubs or enjoy other recreational amenities including a complimentary water park and an outdoor tennis court. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhcpr8972 - Paradise Palms Resort - 4 Bed 3 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 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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Exterior & Views

1834cvt New Solara 9 Bedroom 6 Bathroom Resort

Osceola
1834cvt New Solara 9 Bedroom 6 Bathroom Resort Location
With a stay at this cottage in Kissimmee (Indian Ridge), you'll be a 5-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This spa cottage is 6.8 mi (11 km) from ESPN Wide World of Sports Complex and 7.3 mi (11.7 km) from Old Town.

1834cvt New Solara 9 Bedroom 6 Bathroom Resort Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You can take advantage of recreational amenities such as an outdoor pool and a fitness center.

1834cvt New Solara 9 Bedroom 6 Bathroom Resort Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Sport & Beauty

Grhmap8952 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Osceola
Grhmap8952 - Paradise Palms Resort - 4 Bed 3 Baths 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 family-friendly vacation home is 6.5 mi (10.5 km) from Walt Disney World® Resort and 8.2 mi (13.1 km) from Disney's Animal Kingdom® Theme Park.

Grhmap8952 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Dip into one of the 2 hot tubs or enjoy other recreational amenities including a complimentary water park and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmap8952 - Paradise Palms Resort - 4 Bed 3 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 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.

See details
Fully Booked
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6BR Encore Villa Themed Rooms & Private Pool

Osceola
6BR Encore Villa Themed Rooms & Private Pool Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This family-friendly villa 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®.

6BR Encore Villa Themed Rooms & Private Pool 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.

6BR Encore Villa Themed Rooms & Private Pool Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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Others

Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse

Osceola
Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse Location
When you stay at this villa in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf villa is 7.6 mi (12.2 km) from Disney Springs™ and 8.7 mi (14 km) from Walt Disney World® Resort.

Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse Facility and Service
Pamper yourself with onsite massages or enjoy recreation amenities such as a fitness center.

Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse Rooms
Make yourself comfortable in your villa, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Spacious Condo With Themed Rooms, Foosball Table and Shared Pool

Osceola
Spacious Condo With Themed Rooms, Foosball Table and Shared Pool Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.1 mi (8.3 km) from Disney Springs™ and 5.8 mi (9.4 km) from Walt Disney World® Resort.

Spacious Condo With Themed Rooms, Foosball Table and Shared Pool Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Spacious Condo With Themed Rooms, Foosball Table and Shared Pool Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sophisticated 6BR at Storey Lake SL2766

Osceola
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DISNEY area Luxurious House-Private Pool

Osceola
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Premium Villa at Champions Gate

Osceola
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Parrotfish Place Stay for 6!

Osceola
Parrotfish Place Stay for 6! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 6 mi (9.6 km) from Old Town and 6 mi (9.6 km) from ESPN Wide World of Sports Complex.

Parrotfish Place Stay for 6! Rooms
Make yourself comfortable in this individually decorated vacation home, which features a kitchen. There's a private furnished patio. A 42-inch flat-screen television is provided, with digital programming available.

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5.0/5
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Je63118 - The Encore Club Resort - 6 Bed 5.5 Baths Villa

Osceola
Je63118 - The Encore Club Resort - 6 Bed 5.5 Baths Villa Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly villa is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

Je63118 - The Encore Club Resort - 6 Bed 5.5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Je63118 - The Encore Club Resort - 6 Bed 5.5 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, 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
Enjoy a meal at the restaurant or snacks in the villa's coffee shop/cafe. Quench your thirst with your favorite drink at the bar/lounge.

See details
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Sport & Beauty

Sonoma 3850 IHR 1025

Osceola
Sonoma 3850 IHR 1025 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 9.7 mi (15.6 km) from Disney Springs™ and 10.3 mi (16.6 km) from ESPN Wide World of Sports Complex.

Sonoma 3850 IHR 1025 Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Sonoma 3850 IHR 1025 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private furnished lanai. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a washer/dryer and an iron/ironing board.

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Ov2630 - Bella Vida Resort - 6 Bed 5.5 Baths Villa

Osceola
Ov2630 - Bella Vida Resort - 6 Bed 5.5 Baths Villa Location
With a stay at this villa in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf villa is 8.5 mi (13.7 km) from Disney Springs™ and 8.7 mi (14 km) from ESPN Wide World of Sports Complex.

Ov2630 - Bella Vida Resort - 6 Bed 5.5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2630 - Bella Vida Resort - 6 Bed 5.5 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, 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 villa's coffee shop/cafe, or stop in at the grocery/convenience store. Quench your thirst with your favorite drink at the poolside bar.

See details
Fully Booked
Let's check on other dates!
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Family-friendly Villa w Pool, Hot Tub & Game Room

Osceola
Family-friendly Villa w Pool, Hot Tub & Game Room Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly cottage is 9.9 mi (15.9 km) from ESPN Wide World of Sports Complex and 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park.

Family-friendly Villa w Pool, Hot Tub & Game Room Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a lazy river, and a waterslide. Additional features at this cottage include complimentary wireless internet access, an arcade/game room, and gas grills.

Family-friendly Villa w Pool, Hot Tub & Game Room Rooms
Make yourself comfortable in your air-conditioned cottage.

Restaurant and Cafe
At this cottage, enjoy a satisfying meal at the restaurant. Quench your thirst with your favorite drink at the bar/lounge.

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Interior

Themed Luxury Villa With Star Wars & Mario Magic

Osceola
Themed Luxury Villa With Star Wars & Mario Magic Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This cottage is 8 mi (12.8 km) from Walt Disney World® Resort and 9.6 mi (15.5 km) from Disney's Animal Kingdom® Theme Park.

Themed Luxury Villa With Star Wars & Mario Magic Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Themed Luxury Villa With Star Wars & Mario Magic Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

See details
Fully Booked
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