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28 Holiday homes in Windsor Hills Resort

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28 Results  |  
19 Photos

Villa | 5 Bedrooms | sleeps 14

Excellent 5/5 

5 Nights min stay

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from £100 /night

£695 - £1150 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Stunning 5 bed, 5 bath house with pool & jacuzzi, games room and den in the Windsor Hills gated community, less than 5 minutes from Disney. Our holiday home has over 2,700 square feet of space including 3 king bedrooms and a kids bedroom with 2 sets of bunk beds. Windsor Hills is the most highly rated community in the Orlando area and is less than 2 miles from Disney.  …see more

21 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

1 night min stay

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from £180 /night

£1260 - £1785 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 6 bedroom private villa with private pool, games room in the world renowned gated community of Windsor Hills Resort just 2 miles from the gated of Walt Disney World in Kissimmee, Orllando Florida  …see more

23 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

1 night min stay

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from £150 /night

£1050 - £1700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
6 bedroom 4 bathroom Villa, South facing pool & spa located in the Windsor Hills Resort just 1.5 miles (2.5 km) from the gates of Walt Disney World. The resort offers a variety of recreation and activities for all ages and there are an abundance of golf courses nearby. Rental Period and Occupancy: Check-in time is 4 p.m. Check out time is 10 a.m.  …see more

Featured properties

20 Photos

Townhouse | 3 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

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from £67 /night

£466 - £591 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury 3 bedroom, 3 bathroom home, with splash pool. Located on a holiday resort complex with fabulous facilities, including huge swimming pool with fun slide. Only 2 miles from Disney.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

5 Nights min stay

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from £111 /night

£774 - £1033 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Santa Caterina is located in the beautiful Windsor Hills Resort where you can enjoy all the comforts and amenities of home with all the attractions and the social interactions of a First Class Resort.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

3 Nights min stay

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from £122 /night

£850 - £1300 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
New 2010 Luxury 5 Star, South facing 6 Bed 4 bath Villa. 2 Miles from Dsney. Free calls, Loc, national & international, Free WiFi. Private heated Pool & Spa. Tvs in all rms. Your own games Rm with 42" Lcd & Xbox 360, air hockey, pool tab, foosball & electronic darts. Free Club house with Pool/Jacuzzi , Free tennis courts, Putting green, Basket ball & BBQ area, water slides  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £180 /night

£1260 - £1680 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxury pool villa home with 6 bedroom, 4 bathroom, games room in a world renowned gated community of Windsor Hills resort. Located just 2 miles from the front gates of Walt Disneyland Orlando, Florida.  …see more

10 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £69 /night

£480 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
10 minutes to Disney Gated community giving great security Five star resort with many features close to the house Luxurious family home.  …see more

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

24 Photos

Villa | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £105 /night

£735 - £1083 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
** 2014 discounts available , up to 30% off ** 5 min from Disney! Windsor Hills 5* Gated Resort. Luxury villa. Private South Facing Pool with Spa. Games Room. Free Wi-fi. Resort amenities: Large heated pool, water slide, movie theatre, children's play area. Cable TV. X-box. Close to Restaurants and Outlet Shops. Daily shuttle buses.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £186 /night

£1302 - £1708 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £182 /night

£1274 - £1624 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £189 /night

£1323 - £1876 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £210 /night

£1470 - £1876 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
"Disney Hideaway" town-home has a spacious family room to relax in during the day or evening, with a ceramic tiled floor, contemporary-style interior with beautiful decor, cable TV with a DVD player so you can watch your favorite movie with the whole family. If you need to surf the web  …see more

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Welcome to this beautiful Saddleback Model (1600 sqft.) 3 bedroom 3 bath townhome (2 story) East facing pool This tranquil but pristine three-bedroom, three-bath vacation townhome provides you with everything you will need for the perfect holiday escape. The first floor has an open floor plan with  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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.  In addition to this,  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £215 /night

£1504 - £1904 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Villa La Dolce Vita is new 4 bedroom/4 bathroom Luxury Home that sleeps up to 10 people. Our villa is located in the new five star ***** Windsor Hills Reserve Gated Community, the newest, most luxurious and closest private home resort community to Walt Disney World. We are located less than 2 miles  …see more

24 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £225 /night

£1575 - £2115 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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, and four baths, this property  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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 less than five bedrooms and five  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £189 /night

£1317 - £1646 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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 property can accommodate up to  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £229 /night

£1597 - £2162 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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-car garage, this property can  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £229 /night

£1597 - £2162 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This 2,500 square foot 5B/5B Seville home sleeps 11 and is south facing for year round, all day Florida sun. The fully air conditioned ''dream come true'' home has luxurious tropical furnishings and is professionally decorated throughout. Your every need has been anticipated.  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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 furnished, including the washer and dryer and all new  …see more

20 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Situated in a great location within Windsor Hills, this townhome is sure to delight! Enjoy glorious views of the open park area with gazebo and green space while you relax out at the private splash pool, offering great sun exposure and added privacy with no rear neighbors. This unit is also located  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • 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 vacation now at this beautiful  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

3 Nights min stay

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from £75 /night

£522 - £1053 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A 4 bedroom luxury Villa, with pool,spa and games room at the prestigious Windsor Hills community, within 2 Miles of Walt Disney World. Windsor Hills has a five star clubhouse with Lagoon Pool, hot tub, slides, Cinema, Gym, Games Room, Shop & “Castle” play area.  …see more

17 Photos

Bungalow | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £100 /night

£696 - £718 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Location. Location. Location! We are close to all amenities within the resort ( volleyball, tennis and basketball courts; putting green, large pool, water slide and jacuzzi ; video games and movie theatre) and we are close to all Disney theme and water parks! The resort is just minutes from great places to eat, play, and shop! Enjoy villa living at hotel prices.  …see more

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