Villas in Windsor Hills Resort and Condos - Holiday Lettings - Holiday Rentals Windsor Hills Resort

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22,997 Holiday homes

(4) Excellent 

61

Villa rental in Windsor Hills Resort with swimming pool, balcony / terrace, horse riding from £149/night

Kissimmee / Windsor Hills Resort

5 14 5 nights min

  • 5 bedrooms
  • sleeps 14
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool

from £149 / night

£1,099 / week

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from £149 / night

(13) Very Good 

24

Windsor Hills Resort - villa with a very good review rating | air conditioning & jacuzzi / hot tub | nightlife

Kissimmee / Windsor Hills Resort

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £137 / night

£890 - £1,450 / week

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Responds fast!
avg. 1 hour 42 minutes

from £137 / night

(15) Excellent 

21

Holiday villa rental

Kissimmee / Windsor Hills Resort

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £180 / night

£1,260 - £1,365 / week

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from £180 / night

(10) Very Good 

14

Holiday accommodation in Windsor Hills Resort with great reviews | jacuzzi / hot tub, games room | beach or lakeside relaxation

Kissimmee / Windsor Hills Resort

6 13 3 nights min

  • 6 bedrooms
  • sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £176 / night

£1,223 / week

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Responds fast!
avg. 1 hour 17 minutes

from £176 / night

(5) Very Good 

35

Holiday townhouse with 3 bedrooms and balcony / terrace in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £77 / night

£535 - £918 / week

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from £77 / night

42

3 bedroom accommodation in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £91 / night

£637 / week

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from £91 / night

(14) Excellent 

24

Bungalow in Windsor Hills Resort from £130/night | 4 bedrooms, sleeps 8

Kissimmee / Windsor Hills Resort

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £130 / night

£910 / week

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from £130 / night

(4) Excellent 

20

Villa in Windsor Hills Resort with pool / snooker table from £168/night - Perfect for tennis in town, water sports & golf within 30mins drive

Kissimmee / Windsor Hills Resort

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 116 km
  • Swimming pool
  • Child friendly

from £169 / night

£1,177 / week

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from £169 / night

(13) Excellent 

18

Villa in Windsor Hills Resort with children's pool | golf course on site or within 15 min walk, horse riding & golf within 30mins drive | From £180/night

Kissimmee / Windsor Hills Resort

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £180 / night

£1,260 - £1,365 / week

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from £180 / night

(2) Excellent 

33

Private villa with 5 bedrooms in Windsor Hills Resort | walking holidays, wi-fi and more

Kissimmee / Windsor Hills Resort

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£915 - £1,831 / week

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Responds fast!
avg. 3 hours 55 minutes

from £137 / night

(4) Excellent 

12

Fantastic rental in Windsor Hills Resort, Kissimmee - Great for tennis in town and golf within 30mins drive | swimming pool

Kissimmee / Windsor Hills Resort

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 129 km
  • Swimming pool
  • Child friendly

from £134 / night

£937 - £1,204 / week

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from £134 / night

23

Kissimmee - Check out this amazing 3 bedrooms condo with games room in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning

from £65 / night

£455 / week

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Responds fast!
avg. 3 hours 18 minutes

from £65 / night

(8) Excellent 

28

Spacious self catering property in Windsor Hills Resort | sleeps 8 | tennis in town, city breaks, swimming pool

Kissimmee / Windsor Hills Resort

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £76 / night

£558 / week

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Responds fast!
avg. 1 hour 44 minutes

from £76 / night

18

Enjoy walking holidays and beach or lakeside relaxation in Windsor Hills Resort at this condo from £76/night

Kissimmee / Windsor Hills Resort

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 89 km
  • Swimming pool

from £76 / night

£530 / week

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from £76 / night

38

Windsor Hills Resort villa great for golf within 30mins drive, wi-fi from £149/night

Kissimmee / Windsor Hills Resort

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £149 / night

£1,044 / week

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Responds fast!
avg. 51 minutes

from £149 / night

(3) Excellent 

36

Self-catering townhouse in Windsor Hills Resort with air conditioning & games room - Great for water sports

Kissimmee / Windsor Hills Resort

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 118 km
  • Swimming pool
  • Child friendly

from £107 / night

£744 / week

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from £107 / night

(3)  

14

Get this amazing condo in Windsor Hills Resort from only £68/night ideal for golf course on site or within 15 min walk

Kissimmee / Windsor Hills Resort

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 143 km
  • Swimming pool
  • Child friendly

from £69 / night

£479 - £904 / week

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from £69 / night

Top Destination reviews

Windsor Hills Townhouse, 3 bedrooms, 3 bathrooms
Perfect 'home from home' with great location

This townhouse has a ‘home from home’ feel to it, very clean and well equipped with all the essentials and we were ready to start our holiday right away. Overall, it is spacious and the bedrooms are a good size, with comfortable beds (plenty of pillows and bed linen). Having 3 bathrooms made getting up and out of the house quicker and easier. Especially with having the parks at just a stone’s throw away! (Disney at just a 10 minutes’ drive and Universal just 20 minutes). There are also plenty of restaurants around. The living and kitchen areas are great places to start and end the day with all the necessities needed in the kitchen. The pool area was the perfect touch as well when you want to chill out after a long day at the parks, plenty of space to splash around or enjoy the sunshine. The pool was warm and very clean. If a larger pool is what you want, the complex also has a big shared pool with plenty of loungers and we loved spending the day there. Overall, renting this townhouse was the best way to go. I would definitely recommend and come back here as me and the kids loved it!see more
Beautiful 6 Bedroom Villa at Windsor Hills
Fantastic villa, fantastic location

Great family home and plenty of room for everyone. Close to all the Disney park. Owner and management company were very helpful and responsive. … see more
Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney
Great villa

This villa is located within Windsor Hills which is a perfect location as it's very near Disney. The villa was clean and presented well. We had a few little niggles but I do need to complement both Jennifer and her local management company on response rate and resolution. Thanks … see more
Flagstone Villa
A fantastic place to stay, would highly recommend!

This is a perfect villa for a family holiday to Orlando! The complex is pristine and very safe. The villa itself had everything you could wish for and more. The owners had thought of everything to make our stay comfortable and memorable. The disney parks are 5 minute drive from The Villa, and Universal and Seaworld about 15 minutes so very accessible! We will definitely be staying at Flagstone Villa for our next trip to Orlando!see more
Executive Villa, Pool, Hot tub, WiFi, Games Room
Excellent Villa highly recommend it, great location.

Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant. … see more
Dunestone Villa
Fantastic villa, great location!

Dunestone is a very smart, spacious and well-positioned villa in a great gated community. So close to Disney and only mins from the I-4 allowing easy access to all of Orlando's attractions. The owners were a pleasure to deal with and met all of our requests. We have stayed in several properties in Windsor Hills - Dunestone is most definitely our favourite to date!see more