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39 Holiday homes in Windsor Hills Resort

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39 Results  |  
12 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £167 /night

£1169 - £1645 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

13 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

17 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

Featured properties

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

Villa | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £192 /night

£1341 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 Wor  …see more

17 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

7 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

15 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

16 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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, a game room  …see more

15 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

2 Nights min stay

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from £201 /night

£1405 - £2109 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

14 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

19 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £201 /night

£1405 - £2109 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

18 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

11 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

14 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £167 /night

£1169 - £1449 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable 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

20 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

3 Nights min stay

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from £109 /night

£760 - £928 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Suitable 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 £97 /night

£675 - £696 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

3 Nights min stay

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from £118 /night

£825 - £1300 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable 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

16 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £111 /night

£774 - £1033 / week

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Key info:

  • Swimming pool
  • Suitable 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

20 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £176 /night

£1229 - £1466 / week

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Key info:

  • Nearest beach 116 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
New 2010 - 2 miles to Disney - Luxury 6 bedroom, 4 bath - South facing private Palm Tree lined pool & spa. No expense spared, LCD flat screen TVs in every room, premium & HD cable, Sony BluRay players, Nintendo Wii, Xbox 360, iHome alarm clocks and Bose sound system. Free wi/fi internet and Harley Davidson themed games room with professional pool table and foosball table.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £170 /night

£1190 - £1498 / week

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Key info:

  • Swimming pool
  • Suitable 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 £167 /night

£1169 - £1449 / week

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Key info:

  • Swimming pool
  • Suitable 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 | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £108 /night

£756 - £1113 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
** 2013 discounts available , up to 40% 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 | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £189 /night

£1323 - £1575 / week

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Key info:

  • Swimming pool
  • Suitable 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

19 Photos

Villa | 5 Bedrooms | sleeps 14

Excellent 5/5 

5 Nights min stay

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from £106 /night

£737 - £1060 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
  • Suitable 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

23 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

1 night min stay

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from £159 /night

£1113 - £1696 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

10 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £73 /night

£509 - £742 / week

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Key info:

  • Swimming pool
  • Suitable 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

18 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £191 /night

£1336 - £1818 / week

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Key info:

  • Swimming pool
  • Suitable 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

21 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £191 /night

£1336 - £1818 / week

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Late Deal: save up to £350

Key info:

  • Swimming pool
  • Suitable 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

22 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

1 night min stay

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from £129 /night

£900 - £1050 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 6 Bed/4 Bath Villa - Only 2 miles from Walt Disney World - 28ft private pool  …see more

20 Photos

Townhouse | 3 Bedrooms | sleeps 8

1 night min stay

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from £64 /night

£447 - £607 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable 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

4 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £72 /night

£501 - £649 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Closet vacation rental to Walt Disney World. Comes with linens, towels, and resort amenities such as double Olympic size pool, children's splash park, water slide, spa and more!  …see more

11 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £144 /night

£1008 - £1715 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 5 bedroom, 5 bathroom villa in the gated community of Windsor Hills with private West facing pool with a spa and games room.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £137 /night

£959 - £1372 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This outstanding villa is beautifully furnished and is impressively equipped to exceptional standards. Its location is second to none - just two miles from Disney. With its comfortable 12 person capacity it also provides fantastic value for money.  …see more

11 Photos

Townhouse | 3 Bedrooms | sleeps 8

Short stays welcome

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from £106 /night

£742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Luxury 3 bed home with private pool in The Luxury Windsor Hill's Resort only 1.5 miles from Disney World  …see more

14 Photos

Townhouse | 3 Bedrooms | sleeps 8

Min stay varies

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from £72 /night

£502 - £702 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Windsor Hills exclusive resort in Kissimmee, Orlando. Its fantastic location is only two miles from Disney World and very close other attractions such as Universal Studios. Giant pool and slide, clubhouse, store, movie theater, fitness center.  …see more