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

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21,917 Holiday homes

(13) Very Good 

24

Villa rental in Windsor Hills Resort with golf nearby

Kissimmee / Windsor Hills Resort

6 14 3 nights min

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

from £247 / night

£1,661 / week

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Responds fast!
avg. 1 hour 32 minutes

from £247 / night

(4) Excellent 

20

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Nearest beach 116 km
  • Swimming pool
  • Child friendly

from £195 / night

£1,366 / week

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from £195 / night

42

Condo rental in Kissimmee

Kissimmee / Windsor Hills Resort

3 6 3 nights min

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

from £106 / night

£739 / week

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Responds fast!
avg. 1 hour 43 minutes

from £106 / night

(11) Very Good 

36

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 £205 / night

£1,425 / week

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from £205 / night

(5) 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

from £85 / night

£590 - £1,065 / week

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from £85 / 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

from £224 / night

£1,563 - £2,245 / week

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from £224 / 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

from £207 / night

£1,443 - £2,245 / week

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from £207 / 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 £136 / night

£949 / week

Enquire View

from £136 / night

(4) Excellent 

61

Windsor Hills Resort holiday villa rental

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 £171 / night

£1,259 / week

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from £171 / night

18

Windsor Hills Resort holiday condo let

Kissimmee / Windsor Hills Resort

3 8 min stay varies

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

from £88 / night

£615 - £739 / week

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from £88 / 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 £98 / night

£683 / week

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Responds fast!
avg. 1 hour 21 minutes

from £98 / night

23

Holiday condo in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning

from £79 / night

£621 / week

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Responds fast!
avg. 3 hours 55 minutes

from £79 / 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 £156 / night

£1,087 - £1,397 / week

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from £156 / night

(9) 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 £88 / night

£647 / week

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Responds fast!
avg. 1 hour 45 minutes

from £88 / night

(2) 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 £160 / night

£1,068 - £2,137 / week

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from £160 / 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 £174 / night

£1,215 / week

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Responds fast!
avg. 51 minutes

from £174 / 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 £81 / night

£561 / week

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from £81 / night

Great rentals within 20 miles that match your search

Distance approx 4.83 miles from Windsor Hills Resort Show on Map

16

Davenport holiday villa rental

Davenport / Regal Palms

4 8 4 nights min

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

from £123 / night

£858 / week

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from £123 / night

Distance approx 11.24 miles from Windsor Hills Resort Show on Map

(1) Excellent 

17

Villa letting in Davenport with indoor pool

Central Florida / Davenport

5 12 4 nights min

  • 5 bedrooms
  • sleeps 12
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £400 / night

£2,760 - £2,806 / week

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from £400 / night

Distance approx 5.21 miles from Windsor Hills Resort Show on Map

(8) Excellent 

24

Holiday home with golf nearby in Davenport

Davenport / Davenport City

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £91 / night

£638 / week

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Responds fast!
avg. 1 hour 40 minutes

from £91 / night

Distance approx 5.35 miles from Windsor Hills Resort Show on Map

13

Davenport holiday villa rental

Central Florida / Davenport

3 6 min stay varies

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

from £98 / night

£686 - £873 / week

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from £98 / night

Distance approx 3.65 miles from Windsor Hills Resort Show on Map

6

Home rental in Winter Garden

Central Florida / Winter Garden

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly

from £112 / night

£668 / week

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from £112 / night

Distance approx 4.73 miles from Windsor Hills Resort Show on Map

(1) Very Good 

8

Holiday home in Davenport

Central Florida / Davenport

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Ask owner if suitable for children

from £121 / night

£842 / week

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from £121 / night

Distance approx 12.06 miles from Windsor Hills Resort Show on Map

24

Holiday home in Southport

Florida Panhandle / Southport

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning

from £112 / night

£780 - £905 / week

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Responds fast!
avg. 10 minutes

from £112 / night

Distance approx 1.58 miles from Windsor Hills Resort Show on Map

39

Holiday villa rental

Central Florida / Kissimmee

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £249 / night

£1,158 - £3,047 / week

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Responds fast!
avg. 42 minutes

from £249 / night

Distance approx 7.69 miles from Windsor Hills Resort Show on Map

8

Home rental in Clermont

Lake County / Clermont

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask owner if suitable for children

from £103 / night

£717 / week

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from £103 / night

Distance approx 4.07 miles from Windsor Hills Resort Show on Map

9

Holiday condo in Kissimmee

Central Florida / Kissimmee

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child friendly

from £72 / night

£357 / week

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from £72 / night

Distance approx 13.29 miles from Windsor Hills Resort Show on Map

10

Haines City holiday villa rental

Central Florida / Haines City

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £73 / night

£512 / week

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Responds fast!
avg. 2 hours 36 minutes

from £73 / night

Distance approx 1.1 miles from Windsor Hills Resort Show on Map

8

Four Corners holiday home rental

Central Florida / Four Corners

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask owner if suitable for children

from £107 / night

£749 / week

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from £107 / night

Distance approx 13.83 miles from Windsor Hills Resort Show on Map

18

Holiday villa with swimming pool in Haines City

Central Florida / Haines City

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £96 / night

£667 / week

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Responds fast!
avg. 2 hours 36 minutes

from £96 / night

Distance approx 17.05 miles from Windsor Hills Resort Show on Map

23

Home rental in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

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

from £89 / night

£618 / week

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from £89 / night

Distance approx 6.35 miles from Windsor Hills Resort Show on Map

16

Holiday apartment with shared pool in Kissimmee

Central Florida / Kissimmee

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £71 / night

£489 - £713 / week

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Responds fast!
avg. 3 hours 2 minutes

from £71 / night

Distance approx 0.1 miles from Windsor Hills Resort Show on Map

50

Holiday townhouse with shared pool in Kissimmee

Central Florida / Kissimmee

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £80 / night

£555 - £674 / week

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Responds fast!
avg. 52 minutes

from £80 / night

Distance approx 7.82 miles from Windsor Hills Resort Show on Map

39

Holiday home in Sand Lake

Florida / Sand Lake

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £148 / night

£1,035 / week

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from £148 / night

Distance approx 0.1 miles from Windsor Hills Resort Show on Map

21

Townhouse rental in Kissimmee

Central Florida / Kissimmee

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly

from £80 / night

£555 - £618 / week

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Responds fast!
avg. 52 minutes

from £80 / night

Distance approx 7.67 miles from Windsor Hills Resort Show on Map

20

Holiday home with swimming pool in Celebration

Central Florida / Celebration

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Car not necessary

from £231 / night

£1,616 / week

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Responds fast!
avg. 2 hours 46 minutes

from £231 / night

Distance approx 5.11 miles from Windsor Hills Resort Show on Map

23

Holiday home in Old Town

Florida / Old Town

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly

from £95 / night

£661 / week

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Responds fast!
avg. 1 hour 26 minutes

from £95 / night

Distance approx 5.04 miles from Windsor Hills Resort Show on Map

10

Holiday villa in Loughman

Central Florida / Loughman

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

from £94 / night

£655 / week

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from £94 / night

Distance approx 5 miles from Windsor Hills Resort Show on Map

(1)  

17

Condo rental in Kissimmee with shared pool

Central Florida / Kissimmee

2 8 3 nights min

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

from £151 / night

£1,054 / week

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from £151 / night

Distance approx 0.1 miles from Windsor Hills Resort Show on Map

55

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Pet friendly

from £80 / night

£555 - £646 / week

Book View

Responds fast!
avg. 52 minutes

from £80 / 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
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

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