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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
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Spacious 7bd Pool Gm Hm Terra Verde Resort-211hbl 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
Spacious 7bd Pool Gm Hm Terra Verde Resort-211hbl 7 Bedroom Home 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 9 mi (14.5 km) from Disney Springs™ and 9.3 mi (14.9 km) from Walt Disney World® Resort.

Spacious 7bd Pool Gm Hm Terra Verde Resort-211hbl 7 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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Others

Beautiful 3 Bdrm 2 Bath Condo

Vacation Home

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Osceola
Beautiful 3 Bdrm 2 Bath Condo Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 5.7 mi (9.1 km) from Disney Springs™ and 6.7 mi (10.8 km) from Walt Disney World® Resort.

Beautiful 3 Bdrm 2 Bath Condo Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and barbecue grills.

Beautiful 3 Bdrm 2 Bath Condo Rooms
Make yourself comfortable in this condo, which has a kitchen. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Bedroom

8810geneve

Vacation Home

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Osceola
8810geneve 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 family-friendly vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

8810geneve Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

8810geneve Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a private pool. A kitchen is outfitted with a refrigerator and a microwave. An LCD television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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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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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
Make yourself comfortable in your vacation home.

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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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Chic Property With Private Pool in Encore

Vacation Home

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Osceola
Chic Property With Private Pool 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 vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Chic Property With Private Pool in Encore Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Chic Property With Private Pool 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

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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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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Exterior & Views

Great and practical townhouse in gated community, sleeps 6 10 min to Disney!

Vacation Home

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Osceola
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The Tranquil Townhome - Elegant Townhome in Reunion Resort

Vacation Home

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Osceola
The Tranquil Townhome - Elegant Townhome in Reunion Resort Location
Located in Kissimmee (Reunion), The Tranquil Townhome - Elegant Townhome in Reunion Resort is within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14.1 km) from Old Town.

The Tranquil Townhome - Elegant Townhome in Reunion Resort Rooms
Make yourself at home in one of the individually decorated guestrooms. Bathrooms with bathtubs or showers are provided.

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Championsgate Resort Vacation Pool & Spa Home With Resort Clubhouse Amenity Access 8 Bedroom Home

Vacation Home

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Osceola
Championsgate Resort Vacation Pool & Spa Home With Resort Clubhouse Amenity Access 8 Bedroom Home 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 11.6 mi (18.7 km) from Old Town and 12.4 mi (20 km) from ESPN Wide World of Sports Complex.

Championsgate Resort Vacation Pool & Spa Home With Resort Clubhouse Amenity Access 8 Bedroom 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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Exterior & Views

Dream Vacation Home Close to Disney SL4839

Vacation Home

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Osceola
Dream Vacation Home Close to Disney SL4839 Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 5.6 mi (8.9 km) from Disney Springs™ and 6.6 mi (10.6 km) from Walt Disney World® Resort.

Dream Vacation Home Close to Disney SL4839 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.

Dream Vacation Home Close to Disney SL4839 Rooms
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with a refrigerator and an oven. A flat-screen television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a phone, as well as a microwave and a coffee/tea maker.

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Others

7814 Beechfield Street

Private Vacation Home

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Osceola
7814 Beechfield Street 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 6.2 mi (9.9 km) from Disney's Hollywood Studios® and 7.9 mi (12.7 km) from Disney Springs™.

7814 Beechfield Street Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an indoor pool, and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

7814 Beechfield Street Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a microwave and a coffee/tea maker.

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Bathroom

Colin and Cherryl's Indian Ridge Vacation Home

Vacation Home

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Osceola
Colin and Cherryl's Indian Ridge Vacation Home Location
With a stay at this cottage in Kissimmee (Indian Ridge), you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7.5 mi (12.1 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

Colin and Cherryl's Indian Ridge Vacation Home Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

Colin and Cherryl's Indian Ridge Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen.

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Others

Lovely 5br Townhouse At Windsor At Westside 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Lovely 5br Townhouse At Windsor At Westside 5 Bedroom Townhouse 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 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.

Lovely 5br Townhouse At Windsor At Westside 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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Sport & Beauty

Champions Gate 6BR Sweet Home 9139

Private Vacation Home

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Osceola
Champions Gate 6BR Sweet Home 9139 Location
With a stay at this vacation home in Four Corners, you'll be 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 13.4 mi (21.5 km) from Walt Disney World® Resort.

Champions Gate 6BR Sweet Home 9139 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.

Champions Gate 6BR Sweet Home 9139 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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Championsgate Resort 6 Bedroom Pool Home with Game Room 6 Home

Vacation Home

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Osceola
Championsgate Resort 6 Bedroom Pool Home with Game Room 6 Home 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 Mystic Dunes Golf Club. This vacation home is 11.8 mi (19.1 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 6 Bedroom Pool Home with Game Room 6 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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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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The Watson Court Manor

Vacation Home

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Osceola
The Watson Court Manor Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 2-minute drive from Reunion Resort Golf Course and 10 minutes from ChampionsGate Golf Club. This family-friendly vacation home is 7.6 mi (12.2 km) from Walt Disney World® Resort and 9.5 mi (15.4 km) from ESPN Wide World of Sports Complex.

The Watson Court Manor Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features an arcade/game room, gift shops/newsstands, and gas grills.

The Watson Court Manor Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

See details
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Vacation Homes in Osceola

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