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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
Sport & Beauty

Wonderful 5 Bd W/ Pool @ Storey Lake Resort 2545

Vacation Home

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Osceola
Wonderful 5 Bd W/ Pool @ Storey Lake Resort 2545 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 7.5 mi (12.1 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Wonderful 5 Bd W/ Pool @ Storey Lake Resort 2545 Rooms
Make yourself comfortable in your vacation home.

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3.0/5
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Bathroom

Ov3688 - Compass Bay - 4 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ov3688 - Compass Bay - 4 Bed 2.5 Baths Townhome Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This golf vacation home is 5.4 mi (8.6 km) from Disney Springs™ and 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex.

Ov3688 - Compass Bay - 4 Bed 2.5 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as an outdoor pool. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov3688 - Compass Bay - 4 Bed 2.5 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Modern Luxury Townhome With hot tub & Private Pool - Near Theme Parks

Vacation Home

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Osceola
Modern Luxury Townhome With hot tub & Private Pool - Near Theme Parks 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 11.2 mi (18 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Modern Luxury Townhome With hot tub & Private Pool - Near Theme Parks Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Modern Luxury Townhome With hot tub & Private Pool - Near Theme Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney

Vacation Home

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Osceola
Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney Location
Located in Kissimmee (Reunion), this vacation home is within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This family-friendly vacation home is 6 mi (9.7 km) from Walt Disney World® Resort and 8.1 mi (13 km) from ESPN Wide World of Sports Complex.

Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney Facility and Service
Dip into one of the 8 outdoor pools or enjoy other recreational amenities including a complimentary water park and outdoor tennis courts. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. A flat-screen television with cable programming is available for your entertainment, and a video-game console is also provided. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Others

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 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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Exterior & Views

Mint to Be

Vacation Home

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Osceola
Mint to Be Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 5-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 6 mi (9.7 km) from Old Town and 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex.

Mint to Be Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private furnished patio. A 42-inch flat-screen television is provided, with digital programming available. Conveniences include a separate sitting area and a microwave.

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Others

Windsor_palms_8169n

Vacation Home

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Osceola
Windsor_palms_8169n 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 7.8 mi (12.6 km) from ESPN Wide World of Sports Complex and 8.4 mi (13.6 km) from Disney's Hollywood Studios®.

Windsor_palms_8169n Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Windsor_palms_8169n Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Wired and wireless internet access is complimentary, and a flat-screen television with satellite programming provides entertainment.

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2.0/5
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Exterior & Views

Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning

Vacation Home

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Osceola
Sunshine Park At Windsor Hills 5 Bedroom Villa 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 family-friendly vacation home is 5.2 mi (8.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including complimentary wireless internet access.

Sunshine Park At Windsor Hills 5 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private lanai. Complimentary wireless internet access keeps you connected, and a video-game console is provided for your entertainment. Conveniences include a washing machine and a ceiling fan.

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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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In-room dining

Cozy Family Friendly 4Bd Close to Disney 5149

Vacation Home

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Osceola
Cozy Family Friendly 4Bd Close to Disney 5149 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.6 km) from Walt Disney World® Resort.

Cozy Family Friendly 4Bd Close to Disney 5149 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Cozy Family Friendly 4Bd Close to Disney 5149 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private hot tub and a Smart TV. There's a private balcony or patio. 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.

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4.0/5
Fully Booked
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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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Living area

Buc2999 6 Bedroom Home

Vacation Home

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Osceola
Buc2999 6 Bedroom Home 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 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.2 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Buc2999 6 Bedroom 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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Fully Booked
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Exterior & Views

510 BS - 5BD Elegant Escape: Private Haven

Vacation Home

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Osceola
510 BS - 5BD Elegant Escape: Private Haven Location
When you stay at this vacation home in Kissimmee, you'll be on the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.6 mi (12.2 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

510 BS - 5BD Elegant Escape: Private Haven Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

510 BS - 5BD Elegant Escape: Private Haven Rooms
Make yourself comfortable in your vacation home. Conveniences include an electric kettle and an iron/ironing board.

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Encore Estate, 6br, 10 Min to Disney

Vacation Home

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Osceola
Encore Estate, 6br, 10 Min to Disney 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 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Encore Estate, 6br, 10 Min to Disney Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Encore Estate, 6br, 10 Min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort

Vacation Home

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Osceola
Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.8 km) from Disney's Hollywood Studios®.

Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort Facility and Service
Be sure to enjoy recreational amenities including an outdoor tennis court and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort 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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Eclectic Estate With Location Themed Bedrooms at Reunion

Vacation Home

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Osceola
Eclectic Estate With Location Themed Bedrooms at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Old Town.

Eclectic Estate With Location Themed Bedrooms at Reunion 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.

Eclectic Estate With Location Themed Bedrooms at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

9151 Caddie way

Private Vacation Home

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Osceola
9151 Caddie way Location
When you stay at this vacation home in Four Corners, you'll be near the beach and 7 minutes by car from Highland Reserve Golf Club. This vacation home is 12.6 mi (20.3 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

9151 Caddie way Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an indoor pool, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

9151 Caddie way 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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Sport & Beauty

Ip64049 - Windsor Palms Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ip64049 - Windsor Palms Resort - 3 Bed 3 Baths Townhome 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 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex and 8.2 mi (13.2 km) from Disney's Hollywood Studios®.

Ip64049 - Windsor Palms Resort - 3 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and outdoor tennis courts. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ip64049 - Windsor Palms Resort - 3 Bed 3 Baths Townhome 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.

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Fully Booked
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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.

See details
Fully Booked
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Vacation Homes in Osceola

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