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16 Holiday homes in Windsor Hills Resort

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Filters applied: House (16)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
16 Results  |  
14 Photos

House | 6 Bedrooms | sleeps 12

1 night min stay

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from £110 /night

£770 - £1120 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Windsor Hills 6 bedroom home Gated community  …see more

15 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £209 /night

£1460 - £1973 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Relax in this elegant and professionally decorated 5 bedroom/5 bath pool home, located in the beautiful 5 Star, gated community of Windsor Hills, in Kissimmee, Florida --“Kissimmee Castle." This home has been completely renovated and newly furnishe  …see more

15 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £236 /night

£1646 - £2221 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool and spa located in the Windsor Hills Resort. Atte  …see more

Featured properties

14 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £209 /night

£1460 - £1973 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home with a fantastic view of the lake has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no les  …see more

17 Photos

House | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £270 /night

£1889 - £2556 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This 6 bedroom 4 bath 2,812 sq feet unit sleeps 12 in style. With 2 king bedrooms, 1 queen bedroom, 1 double bedroom and 2 twin bedrooms, there is plenty of room for everyone to spread out and relax after a day out or to just relax and stay in. The dinning room o  …see more

19 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £236 /night

£1646 - £2221 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than six bedrooms, a sofa bed, a  …see more

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £209 /night

£1460 - £1973 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This five bedroom vacation home comes complete with five bathrooms, full kitchen, and pool. This spacious property will easily accommodate 10 on two king, one queen, and four twin sized beds. Amenities include a pool, patio, washer/dryer combo, dishwasher, and hot tub.  …see more

7 Photos

House | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £270 /night

£1889 - £2556 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This very modern 6 bedroom 4 bathroom home has been professionally furnished and decorated including beautiful relaxing colors through-out the home with custom window treatments. No expense has been spared with this home which comes with every little item to make  …see more

18 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £240 /night

£1678 - £2271 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Welcome to this beautiful home in Kissimmee, Florida, featuring tropical furnishings and facing south for Florida sun year round. With five bedrooms and five baths, this place can easily accommodate up to ten people and is perfect for large groups of friends or family.  …see more

15 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £209 /night

£1460 - £1973 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Floor Plan (The Seville) 2,827 sq. ft. 2 story home with pool and spa. (South Facing Pool) We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vaca  …see more

14 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £209 /night

£1460 - £1973 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Floor Plan (The Seville) 2,336 sq. ft. 2 story home with pool and spa (South-West facing pool). We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your  …see more

17 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £240 /night

£1678 - £2271 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Welcome to this elegant, and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. Absolutely perfect for large family groups, this property features all the comforts of home and more! Windsor Hills is a gorgeous gate  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £240 /night

£1678 - £2271 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in Windsor Hills, this beautiful home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than five bedrooms, five baths, and a 2  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £240 /night

£1678 - £2271 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Newly Renovated 5 bedroom, 5 bath property in the 5star gated Windsor Hills community just 5 minutes from Walt Disney World and the surrounding attractions. After an energetic day exploring the sights and sounds of this magical playground you can return home to y  …see more

12 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £196 /night

£1367 - £1730 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With four bedrooms and four baths, this prope  …see more

11 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £209 /night

£1460 - £1973 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than five bedrooms and five bath  …see more