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

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Windsor Hills Resort

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15,968 Holiday homes

42

Condo rental in Kissimmee

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £85 / night

£595 / week

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Responds fast!
avg. 1 hour 57 minutes

from £85 / night

(10) Very Good 

14

Windsor Hills Resort holiday villa let

Kissimmee / Windsor Hills Resort

6 13 3 nights min

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

from £165 / night

£1,143 / week

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Responds fast!
avg. 3 hours 56 minutes

from £165 / night

(14) Excellent 

55

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £129 / night

£900 / week

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from £129 / night

(13) Excellent 

28

Holiday villa in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £130 / night

£910 - £1,200 / week

Enquire View

from £130 / night

(4) Excellent 

20

Villa rental in Kissimmee with golf nearby

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 £158 / night

£1,100 / week

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from £158 / night

15

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 3 nights min

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

from £75 / night

£525 / week

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from £75 / night

(4) Excellent 

61

Windsor Hills Resort holiday villa rental

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool

from £115 / night

£690 - £1,100 / week

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from £115 / night

(13) Very Good 

24

Villa rental in Windsor Hills Resort with golf nearby

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
“Had a wonderful holiday with all the family” Stayed at a very nice villa in a good location a couple of miles from the Disney Parks The surrounding area was always very clean & tidy & well looked after. Could not have asked for anything more, also t
…see more

from £137 / night

£890 - £1,450 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

from £137 / night

(4) Very Good 

35

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“FANTASTIC!” I would highly recommend this 3 bedroom townhouse with heated pool. It was everything and more when we arrived. The outdoor pool was perfect for the kids and the park in the back yard was great to have them play frisbee and soccer. The loc
…see more

from £82 / night

£572 / week

Book View

from £82 / night

(15) Excellent 

21

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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
…see more

from £180 / night

£1,260 - £1,610 / week

Book View

from £180 / night

(13) Excellent 

18

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 ma
…see more

from £180 / night

£1,260 - £1,610 / week

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from £180 / night

(14) Excellent 

24

Holiday bungalow with swimming pool, golf nearby in Windsor Hills Resort

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 £122 / night

£850 / week

Enquire View

from £122 / night

23

Holiday condo 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 £61 / night

£425 / week

Book View

Responds fast!
avg. 3 hours 37 minutes

from £61 / night

(4) Excellent 

12

Windsor Hills Resort holiday home rental

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 £125 / night

£875 - £1,125 / week

Book View

from £125 / night

(8) Excellent 

28

Holiday condo with shared pool in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 2 nights min

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

from £71 / night

£521 / week

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Responds fast!
avg. 3 hours 20 minutes

from £71 / night

(3)  

14

Holiday condo with shared pool, golf nearby in Windsor Hills Resort

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 £65 / night

£450 - £850 / week

Book View

from £65 / night

18

Windsor Hills Resort holiday condo let

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 £71 / night

£495 / week

Book View

from £71 / night

(3) Excellent 

36

Holiday townhouse in Windsor Hills Resort

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 £100 / night

£695 / week

Book View

Responds fast!
avg. 2 hours 0 minutes

from £100 / night

38

Holiday villa with golf nearby in Windsor Hills Resort

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 £140 / night

£975 / week

Book View

Responds fast!
avg. 49 minutes

from £140 / night

(1) Excellent 

33

Holiday villa rental

Kissimmee / Windsor Hills Resort

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £154 / night

£1,000 - £1,715 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from £154 / 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
Joanna and Sams holiday home from home
Luxury in the sun

Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of local restaurants and easy run to NASA. Onsite central facilities were a bonus for time out of the house. Would thoroughly recommend this holiday rental for a relaxing time-out.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