List your home
Apply filters
£ to

Holiday homes 28

Reset search

Filters applied: Wi-Fi available (28)

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
28 Results   |  

Excellent 5/5 

21 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £180 / night

£1260 - £1855 / week

View

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


25 Aug 2015

5/5

"A fantastic villa for all the family"

Stayed in the villa for a week as an extended family of 11 (6 adults and 5 children aged 6 - 11) and couldn't fault a thing. The cleanliness, facilities, layout and set up of the villa was fantastic w… More


8 Nov 2014

5/5

"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 owner… More


21 Jun 2014

5/5

"Great Villa"

We were 2 families who stayed at Dunestone for 2 weeks in May 2014. The villa was lovely and so close to Disney. There is loads of space for everyone and the bedrooms are lovely. The games room was a … More

See all reviews Continue

Excellent 5/5 

16 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £116 / night

£812 - £1085 / week

View

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. ALL PRICES QUOTED INCLUDE 13% FLORIDA TAX Refundable security deposit  …see more


16 Aug 2015

5/5

"Great villa"

This was a great place to stay. Very spacious and well maintained. The swimming pool was excellent. The community is well maintained with good security arrangements. We loved the proximity to DisneyWo… More


7 Jul 2015

5/5

"Live in luxury"

Truly amazing villa, luxury living and everything at hand you could possibly need. Also location is fabulous so close to everything.… More


20 Jun 2015

5/5

"Great location , very nice house, well equipped"

Excellent stay . House is perfect for a large family and clients were very helpful. The location of the house is perfect for the theme parks ,shopping and good restaurant s close by also , added bonus… More

See all reviews Continue

Excellent 5/5 

18 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £180 / night

£1260 - £1855 / week

View

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


6 Dec 2014

5/5

"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 mak… More


6 Dec 2014

5/5

"This house was exactly what my family needed to complete the most amazing trip to Disney World!"

This condo was beautiful and was exactly what we needed to ensure a good night's sleep for all my children (and the adults too). The only thing you would need to know in advance is, you have to buy mo… More


6 Dec 2014

5/5

"Excellent"

Tthe house was nice and clean and located in a quiet and peaceful area close to Diseny. Can be recommended… More

See all reviews Continue

Featured properties

Very Good 4.5/5 

23 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £158 / night

£1100 - £1875 / week

View

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.  …see more


15 Sep 2013

5/5

"Amazing rental a stones throw from disney"

Had a fantastic stay in this home, away from home. A beautiful house equipped with everything a family needs while on holiday, we had a small toddler so this made our holiday so much easier. The hous… More


1 Sep 2013

5/5

"Excellent stay in Windsor Hills Resort Home!!"

We stayed in the Corbett's Windsor Hills home for 10 days during our family vacation to Walt Disney World. It was absolutely perfect for us, it is very spacious and accommodated our large family nicel… More


29 Apr 2014

4/5

"Spacious House"

The house was great very spacious and all 12 of us enjoyed it very much. The downside of getting to a property after being delayed for over 2 hours was it was late at night and other properties we h… More

See all reviews Continue

Excellent 5/5 

10 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £75 / night

£525 - £825 / week

View

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


23 Feb 2015

5/5

"Perfect for a family disney trip!"

Cleanest property we've stayed at in Windsor hills! Love having 3 bedrooms and three full baths. The best value in Kissimmee!!!… More

See all reviews Continue

 

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

 

5 Nights min stay

Add to shortlist

from £207 / night

£1449 - £1876 / week

View

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


2 Jan 2015

1/5

"Overpriced and customer service was non existent for what we paid for"

We were not told and had no idea our accomodation had been changed until we picked up the keys at 11:30 in the night from a safety deposit box outside the offices of the company. When enquiring abo… More

See all reviews Continue

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £210 / night

£1470 - £1624 / week

View

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

Excellent 5/5 

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £128 / night

£895 - £1550 / week

View

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, 6 Bed 4 bath. 2 Miles from Disney. Free calls, Local, national & international, WiFi. South facing Private heated Pool & Spa. Gas BBQ (Grill). Tvs in all rms. Games Rm with 42" Lcd & Xbox 360, air hockey, pool tab, Foosball & electronic darts. F  …see more


26 Oct 2014

5/5

"Excellent villa in a prime location."

Just returned ,top quality villa in a well kept community ,all amenities in villa ,a very short drive to disney and all other main attractions ,5 star.… More


13 Oct 2012

5/5

"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.… More


5 Sep 2012

5/5

"perfect"

we all had a wonderful vacation, mark roche was very helpful from stars to finish, villa was first class, every thing you need is on hand, spotlessly clean, location could not have been better, thank … More

See all reviews Continue

Very Good 4/5 

83 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £67 / night

£468 - £650 / week

View

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


11 Nov 2014

4/5

"A Townhouse is Definitely the Way to Go!"

This townhouse was a great buy for us traveling off season. While we only needed two of the bedrooms, it was nice to be able to split up after a full day at the parks. My teen daughter appreciated s… More

See all reviews Continue

Excellent 5/5 

61 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 14

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £109 / night

£760 - £1000 / week

View

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. Windso  …see more


22 Dec 2014

5/5

"Ideal House and Location"

We had a great holiday in your property. There were 5 of us and we all loved the house and location and we are looking forward to returning at some point in the future, although when that will be I do… More


25 Apr 2014

5/5

"Great house in peaceful environment"

Spacious, comfortable house even for big groups/extended families with a heated pool and all amenities needed. Nice, peaceful and safe environment within a short, easy drive to Disney parks, groceries… More


28 Oct 2011

5/5

"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 … More

See all reviews Continue

23 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 11

1 night min stay

Add to shortlist

from £118 / night

£826 - £1126 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Closest to the Magic! Only 1.5 miles to the gates of the Magic Kingdom. Executive Luxury 5 Bedrooms, 5 Bathrooms FREE WIFI, BBQ gas grill, TV in every room. Amazing Super Hero Games room. Sports theme and Jungle theme bedrooms. Large pool/spa with extended deck Book  …see more

23 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

4 Nights min stay

Add to shortlist

from £200 / night

£1400 - £1500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Windsor Hills Resort clubhouse features a huge lagoon-style pool with water slide and hot tub, children's playground, state-of-the-art fitness center, sand volleyball, basketball and tennis courts, 40-seat movie theatre, video arcade and billiards. Windsor Hills is  …see more

23 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £49 / night

£341 - £773 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Windsor Hills is perhaps the finest resort community in the Disney area. With world famous theme parks and attractions just minutes away, a stay here will create family memories to last a lifetime.  …see more

Excellent 5/5 

17 Photos

Kissimmee / Windsor Hills Resort

Bungalow / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £107 / night

£746 / week

View

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 resor  …see more


8 Jan 2015

5/5

"Excellent place to call home for the fortnight!"

Lovely villa supplied with everything you need for a comfortable stay. Communication with the owner and the rental company was first class who made the whole booking experience a pleasure. Close to … More

See all reviews Continue

Very Good 4/5 

20 Photos

Kissimmee / Windsor Hills Resort

Villa / 4 Bedrooms / sleeps 8

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £81 / night

£565 - £1310 / week

View

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


5 Sep 2013

4/5

"Lovely villa in a super location"

We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the … More

See all reviews Continue

16 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £126 / night

£878 - £1294 / week

View

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 floo  …see more

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £182 / night

£1274 - £1624 / week

View

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

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £186 / night

£1302 - £1708 / week

View

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

20 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £151 / night

£1056 - £1549 / week

View

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 neighb  …see more

8 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £151 / night

£1056 - £1549 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
2 story town home with splash pool (North facing pool) 3 bedroom/3 bath townhome in gated Windsor Hills community, just minutes from Disney World. Sleeping accommodations include 1 king size, 1 queen, and 2 twin sized beds for 8 guests. Also, this property has a heatabl  …see more

24 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £260 / night

£1819 - £2455 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Welcome to this newly decorated 5 bedroom pool home located in Windsor Hills. There are also 5 bathrooms in this smart floor plan! So, everyone has plenty of space and all can get ready for the day at their own pace. The kitchen has been fully renovated and includes upg  …see more

17 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £260 / night

£1819 - £2455 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Welcome to this stunning 5 Bedroom, 5 Bathroom pool home, with spa, in popular Windsor Hills Resort. One of the benefits of renting a vacation home is that everyone can have their own bedroom for privacy. The unique feature of this beautiful home is that there are 5 bat  …see more

13 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £260 / night

£1819 - £2455 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
We are proud to offer this elegant 5 bedroom, 5 bathroom vacation villa in Windsor Hills. This home is tastefully painted throughout and features leather furniture in the living room. There are bunk beds for the kids along with a set of twin beds in the Mickey bedroom.  …see more

14 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £299 / night

£2088 - £2825 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Sevillle floor plan 2236sqft 5 bedroom 5 barth (2 story) Pool home We invite you to enjoy your next vacation at our luxurious, brand new and beautifully decorated 5 bed/5 bath Home with 28ft pool. Sleeping accommodation features two elegant master suites with king size  …see more

14 Photos

Kissimmee / Windsor Hills Resort

House / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £295 / night

£2062 - £2776 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Floor Plan (Brentwood) 2,812 sq. ft. 2 story home with pool and spa (North-east facing pool) Executive waterfront villa. Extra privacy with no rear neighbors overlooking the pool/spa area. Furnished by a professional interior design firm along with custom made furniture  …see more

14 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £299 / night

£2088 - £2825 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Floor Plan (The Seville) 2.336 sq. ft 2 story home with pool & spa (West facing pool) Beautifully furnished and decorated 5 Bedroom 5 bathroom vacation home with private screened in Pool and spa heated upon request with extra charge. Back yard faces west with sun in aft  …see more

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £130 / night

£905 - £1585 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Spread out and enjoy a sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World! FROZEN Themed Bedroom NO REAR NEIGHBOURS! To ensure your privacy, our pool overlooks a natural area, not another house! Specia  …see more

21 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 10

1 night min stay

Add to shortlist

from £151 / night

£1055 - £3346 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Lagoon-style pool/water park complex-State of the art fitness center-Game room with billiard and table tennis-Video Arcade-Grocery and sundries shop-Private high-def surround sound movie theater-Tennis and volleyball courts-Children's playground- 24 hr gated entrance  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page