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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
Bedroom

Regal Oaks Resort

Vacation Home

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Osceola
Regal Oaks Resort Location
With a stay at this vacation home in Kissimmee, you'll be a 1-minute drive from Old Town and 8 minutes from Walt Disney World® Resort. This vacation home is 4.3 mi (7 km) from ESPN Wide World of Sports Complex and 4.6 mi (7.4 km) from Disney's Hollywood Studios®.

Regal Oaks Resort Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and charcoal grills.

Regal Oaks Resort Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a Smart TV. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a coffee/tea maker and a ceiling fan.

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5.0/5
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Others

8931 Candy Palm RD

Private Vacation Home

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Osceola
8931 Candy Palm RD Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This golf vacation home is 6.5 mi (10.5 km) from Walt Disney World® Resort and 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park.

8931 Candy Palm RD Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and barbecue grills.

8931 Candy Palm RD Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A 40-inch flat-screen television is provided, with digital programming available. Conveniences include a microwave and a coffee/tea maker.

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

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The Themepark Palace With Home Theater at Encore

Vacation Home

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Osceola
The Themepark Palace With Home Theater at Encore Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly villa is 5.7 mi (9.1 km) from Walt Disney World® Resort and 7.9 mi (12.7 km) from ESPN Wide World of Sports Complex.

The Themepark Palace With Home Theater at Encore Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

The Themepark Palace With Home Theater at Encore Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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Condominium House Orlando Florida

Vacation Home

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Osceola
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Others

Storey Lake 6 Bedroom Vacation Home 4712

Vacation Home

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Osceola
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Interior

Db2633 Windsor Hills Resort Vacation Home

Vacation Home

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Osceola
Db2633 Windsor Hills Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Old Town.

Db2633 Windsor Hills Resort Vacation Home 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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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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Pool

Paradise Palms 5 Bedroom Vacation Home 8954

Vacation Home

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Osceola
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Family & Kids

Disney Getaway: Pool, Spa & Lake Views

Vacation Home

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Osceola
Disney Getaway: Pool, Spa & Lake Views 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 (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Disney Getaway: Pool, Spa & Lake Views 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.

Disney Getaway: Pool, Spa & Lake Views 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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Others

630sst- The Retreat at Championsgate

Vacation Home

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Osceola
630sst- 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 Four Corners FC. This golf vacation home is 12.4 mi (20 km) from Old Town and 13 mi (20.9 km) from ESPN Wide World of Sports Complex.

630sst- The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

630sst- The Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

4337 QS - Charming Hideaway

Vacation Home

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Osceola
4337 QS - Charming Hideaway 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 6.9 mi (11.1 km) from Disney Springs™ and 7.6 mi (12.3 km) from Walt Disney World® Resort.

4337 QS - Charming Hideaway Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including barbecue grills.

4337 QS - Charming Hideaway Rooms
Make yourself comfortable in your vacation home. There's a private patio. Satellite television is provided for your entertainment. Conveniences include a desk and an electric kettle.

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Windsor Hills by Nova

Vacation Home

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Osceola
Windsor Hills by Nova Location
Located in Kissimmee (Windsor Hills), Windsor Hills by Nova is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 6.1 mi (9.8 km) from Disney's Hollywood Studios® and 7.8 mi (12.5 km) from Disney Springs™.

Windsor Hills by Nova Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as an outdoor pool or a waterslide.

Windsor Hills by Nova Rooms
Make yourself at home in one of the 26 air-conditioned rooms featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private furnished lanais. Flat-screen televisions and video-game consoles are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include microwaves and coffee/tea makers, as well as phones with free local calls.

Important Information
This property is closed from June 6 2025 to June 5 2027 (dates subject to change).

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3.0/5
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Others

Grhbuc2960 - Paradise Palms Resort - 6 Bed 5 Baths House

Vacation Home

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Osceola
Grhbuc2960 - Paradise Palms Resort - 6 Bed 5 Baths House 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 8.6 mi (13.8 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Grhbuc2960 - Paradise Palms Resort - 6 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.

Grhbuc2960 - Paradise Palms 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
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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Fully Booked
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Exterior & Views

Luxe Reunion House w/ Private Pool: Near Disney!

Private Vacation Home

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Osceola
Fully Booked
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Others

Grhbch3061 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhbch3061 - 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 8.1 mi (13 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.4 km) from ESPN Wide World of Sports Complex.

Grhbch3061 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse 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 a television in a common area.

Grhbch3061 - 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 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. 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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Mvv7460 - 3BR House Near Disney w/ Hot tub

Vacation Home

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Osceola
Mvv7460 - 3BR House Near Disney w/ Hot tub Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This cottage is 4.7 mi (7.5 km) from ESPN Wide World of Sports Complex and 5.2 mi (8.3 km) from Disney's Hollywood Studios®.

Mvv7460 - 3BR House Near Disney w/ Hot tub Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Mvv7460 - 3BR House Near Disney w/ Hot tub Rooms
Make yourself comfortable in this air-conditioned cottage, which features a fireplace. A kitchen is outfitted with an oven, a stovetop, and a microwave. Conveniences include a washer/dryer and an iron/ironing board.

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Bedroom

4 Bdrm With Private Pool

Private Vacation Home

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Osceola
4 Bdrm With Private Pool Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 11.4 mi (18.4 km) from Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

4 Bdrm With Private Pool Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

4 Bdrm With Private Pool Rooms
Make yourself comfortable in this air-conditioned vacation home, 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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Room

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC

Vacation Home

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Osceola
Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Location
With a stay at this vacation home in Kissimmee (Lake Berkley), 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 9.2 mi (14.8 km) from Walt Disney World® Resort.

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Sport & Beauty

West Lucaya Resort

Private Vacation Home

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Osceola
West Lucaya Resort Location
When you stay at this vacation home in Kissimmee, you'll be in the entertainment district, within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.5 mi (12.1 km) from Disney's Animal Kingdom® Theme Park and 8.7 mi (14.1 km) from Old Town.

West Lucaya Resort Facility and Service
Don't miss out on recreational opportunities including a hot tub and a fitness center.

West Lucaya Resort Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave.

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Artistic Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Artistic Townhouse With Games Room at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be 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 km) from Old Town.

Artistic Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Vacation Homes in Osceola

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