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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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Grhmvd1638 - Champions Gate Resort - 6 Bed 5 Baths House

Vacation Home

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Osceola
Grhmvd1638 - Champions Gate Resort - 6 Bed 5 Baths House 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 family-friendly 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.

Grhmvd1638 - Champions Gate Resort - 6 Bed 5 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1638 - Champions Gate Resort - 6 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
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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Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer

Vacation Home

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Osceola
Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer 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 family-friendly vacation home is 11.5 mi (18.6 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer Facility and Service
Enjoy a range of recreational amenities, 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.

Modern Townhome With Private Pool, hot Tub, Central AC, and Private Washer/dryer Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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2767lkd-emerald Island Resort 7 Bedroom Home

Vacation Home

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Osceola
2767lkd-emerald Island Resort 7 Bedroom Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.2 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.4 km) from Disney's Hollywood Studios®.

2767lkd-emerald Island Resort 7 Bedroom Home Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Deluxe Mansion With Swim up Bar and Pool Slide at Reunion

Vacation Home

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Osceola
Deluxe Mansion With Swim up Bar and Pool Slide at Reunion 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 vacation home is 6.9 mi (11.1 km) from Walt Disney World® Resort and 8.9 mi (14.3 km) from Old Town.

Deluxe Mansion With Swim up Bar and Pool Slide at Reunion Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Deluxe Mansion With Swim up Bar and Pool Slide at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Grhmvd1508 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhmvd1508 - Champions Gate Resort - 6 Bed 6 Baths House Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 11.8 mi (18.9 km) from Old Town and 12.5 mi (20.2 km) from ESPN Wide World of Sports Complex.

Grhmvd1508 - Champions Gate Resort - 6 Bed 6 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1508 - Champions Gate Resort - 6 Bed 6 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
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Beautiful Large Pool Area 6 Bedroom Home! 6 Home by RedAwning

Private Vacation Home

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Osceola
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Paradise Palms Resort, Just Minutes From Disney!!!!

Vacation Home

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Osceola
Paradise Palms Resort, Just Minutes From Disney!!!! 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 vacation home is 8.6 mi (13.8 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Paradise Palms Resort, Just Minutes From Disney!!!! Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an indoor pool, and a fitness center.

Paradise Palms Resort, Just Minutes From Disney!!!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Spacious Townhouse With Private Patio and Resort Amenites

Vacation Home

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Osceola
Spacious Townhouse With Private Patio and Resort Amenites Location
When you stay at this condo in Four Corners, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This condo is 10.9 mi (17.6 km) from Walt Disney World® Resort and 11.9 mi (19.2 km) from Old Town.

Spacious Townhouse With Private Patio and Resort Amenites Facility and Service
Be sure to enjoy recreational amenities, including a hot tub, an outdoor tennis court, and a fitness center. This condo also features complimentary wireless internet access and an arcade/game room.

Spacious Townhouse With Private Patio and Resort Amenites Rooms
Make yourself comfortable in your individually decorated condo. The bathroom has a bathtub or shower.

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Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub

Vacation Home

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Osceola
Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub Location
When you stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.9 mi (19.1 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Luxury Resort Home With Themed Rooms, air Hockey, Pool Table, Pool and hot tub Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Fv62887 - Paradise Palms - 4 Bed 3.5 Baths Townhome

Vacation Home

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Osceola
Fv62887 - Paradise Palms - 4 Bed 3.5 Baths Townhome 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 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Fv62887 - Paradise Palms - 4 Bed 3.5 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and gift shops/newsstands.

Fv62887 - Paradise Palms - 4 Bed 3.5 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. Wrap up your day with a drink at the poolside bar.

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Bedroom

UpstaySpaciousHomePoolHotTubSleeps27

Vacation Home

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Osceola
UpstaySpaciousHomePoolHotTubSleeps27 Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.6 mi (15.5 km) from Disney Springs™ and 10.7 mi (17.2 km) from Walt Disney World® Resort.

UpstaySpaciousHomePoolHotTubSleeps27 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and an indoor pool.

UpstaySpaciousHomePoolHotTubSleeps27 Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and a washer/dryer.

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Spacious Home With South Facing Pool in Encore

Vacation Home

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Osceola
Spacious Home With South Facing 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 ChampionsGate Golf Club. This vacation home is 5.5 mi (8.9 km) from Walt Disney World® Resort and 7.8 mi (12.5 km) from ESPN Wide World of Sports Complex.

Spacious Home With South Facing Pool in Encore Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Home With South Facing Pool in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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Relaxing Oasis, Pool & Spa, Minutes From Disney

Vacation Home

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Osceola
Relaxing Oasis, Pool & Spa, Minutes From Disney 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 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Relaxing Oasis, Pool & Spa, Minutes From Disney Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Relaxing Oasis, Pool & Spa, Minutes From 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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Luxury Town With Splash Pool In Solara Resort 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Luxury Town With Splash Pool In Solara Resort 4 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be 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 (16.8 km) from Disney's Animal Kingdom® Theme Park.

Luxury Town With Splash Pool In Solara Resort 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a microwave and a dishwasher. Complimentary wireless internet access is available to keep you connected.

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Grhcdw9157 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhcdw9157 - Champions Gate Resort - 6 Bed 6 Baths House 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 family-friendly vacation home is 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

Grhcdw9157 - Champions Gate Resort - 6 Bed 6 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcdw9157 - Champions Gate Resort - 6 Bed 6 Baths House 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 television is provided for your entertainment.

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.

See details
Fully Booked
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Sport & Beauty

Beautiful Renovated 6 Bed Pool Home 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Beautiful Renovated 6 Bed Pool Home 6 Bedroom Home by RedAwning Location
Located in Kissimmee (Veranda Palms), this vacation home is within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.7 mi (10.9 km) from Disney Springs™ and 7.8 mi (12.5 km) from Walt Disney World® Resort.

Beautiful Renovated 6 Bed Pool Home 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a microwave. Complimentary wireless internet access is available to keep you connected.

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Spacious 5 Bed Pool Home With Game Room-1544mvd 5 Bedroom Home

Vacation Home

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Osceola
Spacious 5 Bed Pool Home With Game Room-1544mvd 5 Bedroom Home Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.3 mi (18.1 km) from Walt Disney World® Resort and 11.6 mi (18.7 km) from Old Town.

Spacious 5 Bed Pool Home With Game Room-1544mvd 5 Bedroom Home Rooms
Make yourself comfortable in your vacation home. There's a private patio. Complimentary wireless internet access is available to keep you connected. Conveniences include a desk and a washing machine.

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Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly

Vacation Home

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Osceola
Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly Location
With a stay at this vacation home in Kissimmee (Lindfields), you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.3 mi (11.8 km) from Disney's Animal Kingdom® Theme Park and 8.4 mi (13.5 km) from Old Town.

Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Private kitchen

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161

Vacation Home

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Osceola
Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161 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 5.8 mi (9.3 km) from ESPN Wide World of Sports Complex.

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161 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.

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. 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 60-inch Smart television with cable programming provides entertainment.

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3.8/5
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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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Vacation Homes in Osceola

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