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Windsor Hills Luxury 4 Bed 4 Bath Villa in Kissimmee

All Bedrooms Have 32" TV and Own Ensuite | Disney and Frozen Themed Twin Rooms | Pool and Spa | Gamesroom | Close to Sunset Walk / Margaritaville on HWY 192 and Disney's Animal Kingdom

Windsor Hills Resort

4 bedrooms (sleeps 8)

4 bathrooms (4 en-suites)

Property ID: 405

From (GBP) £1395 / week

Contact Details

Claire - Villas In Florida 2 Rent

+44 07419 821288
NO RESORT FEES - Rate quoted is for a low season stay and includes all local taxes. Calendars are automatically updated daily. Over 210 Five Star Business Reviews on Google! Special Offer - Book with Just £195 Deposit.

Languages: English

Joined 2008

Over 15 years of selling Florida Tickets Over 15 years of selling Florida Tickets
  • Pool
  • Windsor Hills Resort 4 Bedroom 4 Bath Vacation Rental
  • Family Room with 52" TV
  • Family Room
  • Family Room
  • Dining Area
  • Kitchen with Breakfast Bar
  • Breakfast Nook with Access to the Pool
  • King Master Bedroom
  • Master Bedroom with Access to the Pool
  • 32" TV
  • Ensuite Shower Room to Master Bedroom
  • 2nd Master Bedroom (at front of villa)
  • 2nd Master Bedroom (at front of villa)
  • Ensuite Bathroom to 2nd Master Bedroom
  • Mickey Twin Room
  • Ensuite Shower Room to Mickey Room
  • Frozen Twin Bedroom
  • Frozen Twin Bedroom
  • Ensuite Shower Room
  • Gamesroom
  • Large Lanai
  • Under Cover Lanai
  • Pool and Spa
  • Pool and Spa
  • Image 64
  • Under Cover Lanai
  • Back of the Villa
  • On Disney's Doorstep
  • Large Party - Book neighbouring 4 bed villas
  • 24 Hour Gated Entrance
  • Windsor Hills Clubhouse
  • Open Clubhouse
  • New Slides and Splash Zone
  • New Slides and Splash Zone
  • New Slides and Splash Zone
  • Lagoon Pool
  • Lagoon Pool
  • Zero level entrance
  • Lagoon Pool
  • Lagoon Pool
  • Gamesroom
  • Gamesroom
  • Cinema
  • Cinema
  • Windsor Hills Clubhouse Facilities
  • Guilt Free Gym!
  • Guilt Free Gym!
  • On site shop
  • On site shop
  • Windsor Hills Clubhouse Facilities
  • Windsor Hills Clubhouse Facilities
  • Play Area
  • Play Area
  • Mini Golf
  • Mini Golf
  • Image 52
  • Play Area
  • Play Area
  • Play Area
  • Play Area
  • Close to Sunset Walk
  • Close to Sunset Walk


Fabulous 1,816 sq ft, 4 Bedroom 4 Bath Pool Home in the guarded and gated community of Windsor Hills!

This luxury Orlando vacation villa is a four bedroom, four baths, pool and spa home located in the brand new, exclusive rental community of Windsor Hills Reserve, less than five minutes from Walt Disney World!

Windsor Hills has excellent resort style facilities including a clubhouse with large communal pool, water slide, large hot tub and childrens fountain area. Inside the clubhouse there is a sundry shop selling snacks, beers and everyday items there is also a fitness center, cinema room, arcade games and pool tables.


The home has a well established mangement company in Orlando. In addition to ensuring the villa fully complies with Florida State licensing requirements for rented accommodation, they ensure the house is maintained in top condition and are on hand in the event you need assistance during your stay.

For your convenience, you are given a code to access the home, without having to drive to a key collection point or worry about contacting the management company if your travel arrangements are running behind schedule.


As you enter the home the family room is your first stop, with a large leather sofa to slouch in front of the 52" Plasma TV.


Upgraded appliances and cabinets in the fully equipped gourmet kitchen, allow you to cook a meal at home and rest after a day at the park. You also have a washer, dryer and ironing facilities.


You have two eating areas in the home, a more formal setting and a large breakfast table, both overlooking the pool at the rear of the villa.


4 bedrooms, sleeps 8.

Master Bedroom - King bed, 32" TV, access to pool, ensuite double shower room

2nd Master Bedroom - King bed, 32" TV, ensuite bathroom with shower over bath

Frozen - Twin Beds, 32" TV, ensuite bathroom with shower over bath

Mickey - Twin Beds, 32" TV, ensuite double shower room

Added Luxury's - Pillow Top Matresses, luxury towels and linens.


4 bathrooms, 4 en-suites.

Games Room

Fun-filled game room with SNES system connected to 42" TV, Air Hockey Table and Fooseball Table


FREE use of the in home wireless internet.

Baby Equipment

Baby Equipment can be hired locally.

Wheelchair Accessible - No
Pets Considered - No


Windsor Hills Resort Clubhouse with Water Slides and Splash Park

PLEASE NOTE - The clubhouse pool will be closed for resurfacing for 4 weeks in September 2024, the start date is weather dependant, so this could also run into the beginning of October 2024.  The resurfacing is essential to maintain the quality and safety of the pool for everyone's benefit.

Windsor Hills Resort Villas & Vacation Rentals By Owner in Orlando, Florida. Situated in the heart of Kissimmee and less than 3 miles from the Disney's main gate.

This upscale and very popular gated resort maintains its exclusive feel and privacy with the benefit of 24 hr security. We have a selection of over 40 luxury Windsor Hills vacation rentals and villas. Consider Windsor Hills for your next Florida holiday, all with private pools and many with spas. NO SERVICE FEES

The Windsor Hills Resort clubhouse pool was extended to include slides and a splash pad for kids.  This is a fantastic addtion to the Orlando resort and we know guests are going to love it. Please see the video below which shows the Windsor Hills Resort water slides and splash pad. 

Windsor Hills Resort Youtube Video

Windsor Hills Resort Rentals from 3 - 6 Bedrooms

All our Windsor Hills Orlando rental villas have fully equipped kitchens. So you can cook a four course meal if you like. They all also have laundry rooms with washers, dryers and ironing boards. Don't live out of a suitcase while on holiday! One of the great things about the Windsor Hills villas is the ratio of bathrooms to bedrooms. Meaning you don't have to share if you don't want too. Many of the 4 and 5 bedroom vacation homes having all en-suites. Even the 6 bedroom Windsor Hills villas have 4 or 5 bathrooms. With at least 3 en-suites making them ideal for large families.

Windsor Hills Resort Vimeo Video

A lot of the Windsor Hills Resort vacation rentals have themed bedrooms. Some of the most popular are Mickey Mouse, Princess, Tinker Bell, Harry Potter and even a Pirates of the Caribbean. A great treat for the kids and something a little bit different to the normal rooms.

Less than 30 mins from Orlando International Airport

We have added details of how to get from Orlando Airport to the Windsor Hills Resort. Please check out our blog post - Driving Direction from Orlando Airport (MCO) to the Windsor Hills Resort

Most of our Windsor Hills vacation rentals by owner have games rooms. With pool tables, table football, darts and even bikes for the kids. Some may also include tennis rackets for use on the free courts.

Lots of owners have added games consoles, ideal to keep the kids happy after a long day at the parks. Let them play while you relax by the pool with a glass of wine. Please check each of the Windsor Hills Resort rental homes descriptions to see what games consoles they have. One thing to note, if you are coming from the UK your games won't work on the US systems.

A great feature that all the Windsor Hills villas have is a covered area by the pool. This is known as the lanai. Great for the summer months when it 100F and you want a little shade. It's also it's ideal for small children to play in without the fear of getting burnt. Florida is known for having some amazing storms especially in the summer months. Having the covered lanai allows you sit outside and watch them with a cold drink which can be great fun.

The Windsor Hills Clubhouse is Open All Year Round

The Windsor Hills Orlando Resort also has a clubhouse which is open to guests all year round. It features a large communal pool with water slide and hot tub. Loads of sun loungers so you can choose to sit in the sun or shade.

Windsor Hills also has a sundry shop open from 8am - 10pm everyday selling groceries, newspapers, drinks, ice creams and toiletries. If the xbox isn't enough to keep the kids busy then the clubhouse has a games arcade and pool room.

If you want to have a workout the Windsor Hills clubhouse has a state of the art gym. This is also open to all guests free of charge. The Windsor Hills clubhouse also has a 50 seater cinema. Showing movies daily so please check with clubhouse reception to see what's playing.

Watch a Movie in the 50 Seater Clubhouse Cinema

There are also two on site playgrounds with swings, slides and roundabouts. Tennis and basket balls courts with flood lights. And a 7 hole putting green and sand volleyball court. You will need to take your own equipment for all the courts.

No matter what you are looking for Windsor Hills Resort has it covered. This is why it's one of the most sort after Florida vacation rental communities in Orlando.

We have luxury Windsor Hills vacation rentals located across the whole community. With a great choice of different accommodation for this popular Orlando community.

Over 25 Golf Courses within 15 mins of Windsor Hills

Keen golfers will be pleased to note Windsor Hills Resort is directly next to the Mystic Dunes Golf Course. This is one of the best golf courses in Orlando and a great test for all skill levels.

Other golfs courses within 5 minutes of Windsor Hills include Falcons Fire, Celebration and the 4 courses at Disney World. The Disney courses are the home of the Children's Miracle Classic PGA Tour Event. This is played in November on the Magnolia and Lake Buena Vista courses.

There are another 25 golf courses within 15 minutes of Windsor Hills Resort. And over 100 within 60 minutes so you will never have to play the same course twice.

Within a 2 mile radius of the Windsor Hills Resort is a Publix supermarket. There is also a brand new Wal-Mart, a Walgreen's pharmacy and numerous restaurants. There are actually so many restaurants you can eat somewhere different every night!

Windsor Hills Reserve was the second part of the Windsor Hills Resort to be built. The whole resort community is now complete.

We have a selection of Windsor Hills Florida rentals available. Please contact them direct to ask any question, check availability or book. Don't just take our word for it you can also read Windsor Hills villa reviews from previous guests. To see the reviews click on the review stars or go to the review tab for each villa listing.

Driving Distances from the Windsor Hills to the Orlando Theme Parks

We have added the actual driving distances to all the main Orlando theme parks below. These are not the distances to the main gate which most people quote. These are the distances to the actual car park for each attraction. Most journeys to the Orlando theme parks are via highways or interstates. Driving at speeds between 55-65 MPH so it's pretty quick to get to all of them.

  • Animal Kingdom - 3 miles
  • Hollywood Studios - 5.5 miles
  • Magic Kingdom - 7 miles
  • Epcot - 7 miles
  • SeaWorld - 11.5 miles
  • Universal Studios - 15.5 miles

Things to know when staying at the Windsor Hills Resort

We have put together some blog posts that we hope will help your stay on the Windsor Hills Resort. They have lots of FAQ's so please check it out - Windsor Hills Resort Review and Tips

Restaurants near the Windsor Hills Resort

We have put together a list of over 50 restaurants along HWY192 in Kissimmee. These are all less than 5 minutes away from the Windsor Hills Resort. The list includes links to menus as well as google / trip advisor reviews. There is so much choice that you should be able to eat somewhere different every night.

Other Nearby Orlando Communities

If you can't find what you are looking for on the Windsor Hills Resort below is a list other nearby vacation rental communities. We have over 850 Orlando villas to rent on 100 different communities so you should be able to find something that suits your needs.



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Rental rates quoted in (approx)

£1395 / week

Rental rates additional information

The weekly rate quoted above is based on a low season stay and includes local taxes. Please contact us through the site for a personalised quote based on the dates you require; rates are not guaranteed until a deposit has been paid. Optional pool heating can be added for the winter months. If booking within 12 weeks of rental then payment is due in full, otherwise you can secure your dates with a 25% non-refundable deposit. A cleaning fee is added to any booking under 7 nights.


Have you stayed here? Share your thoughts – 

write a review

Thanks Claire, I had a great time! The location of the villa - about 10 mins from Disney and 5 mins from the supermarket is a massive bonus!

Date of stay:     Reviewer name: , Wrexham

First Class!

A first-class stay with first-class customer care from Claire. The villa was absolutely lovely and a fantastic location for our trips into WDW. Highly recommended and all being well, we would love to stay again!

Date of stay:     Reviewer name: , Preston

Villa was Great

Lovely 4 bedroom villa with plenty of room. One couple, plus 1 adult and 2 older children. The extras in the garage are so thoughtful if you have kids, prams, umbrellas, water wings etc. w/machine and t/dryer is a godsend. Villa was lovely and clean and a folder on hallway desk to explain how you use everything. Guest book to sign too. The pool area is good size for us all. Good outdoor seating. Disney is about 15 mins in a uber so super close and Uber's are cheaper than car hire. It's $30 to park in Disney, so, we didn't use our car. About 15 min walk to resort pool, which is safe and secure. Good cafe with games room and gym. Nice clean toilets with showers. Claire is great at booking our villas, knows what we like, we have used her the last 3 visits and is always on hand, bless her!

Date of stay:     Reviewer name: , Kent

Great Time..

In 2022 we finally made it back to Florida! We originally booked for 2020 but, of course, Covid changed things somewhat! Throughout the whole period of uncertainly Claire was helpful and above all, flexible as we had to keep changing our booking dates. We returned from staying in Windsor Hills, which is a winner in terms of location for parks and restaurants along the 192. The house was clean and well equipped. We had a great time and wouldn't hesitate to use Claire (Villa2Rent) again having used them on a previous visit in 2011. We will no doubt return :-)

Date of stay:     Reviewer name: , Harrow, Middx

Windsor Hills SO good for the Disney parks!

We booked this villa a trillion years ago, or so it felt, before Covid and thankfully got to stay last week. Claire has been incredibly wonderful at re booking us and sorting our different dates each year. Everything was so organised and Claire was incredibly efficient. The house was perfect for two families and Windsor Hills SO good for the Disney parks! Easiest drive ever.

Date of stay:     Reviewer name: , Windsor, Berkshire


Claire was super helpful with the booking throughout the process, very good communication and the villa was just as expected - great! Would reach out to Claire for next time for sure.

Date of stay:     Reviewer name: , Glasgow


Fantastic stay in Windsor hills resort as always. Third time staying in the two neighbouring villas - absolutely perfect for our party of 9 - gorgeous, spacious and super clean villas with plenty of space and big pools which kids were never out of when we were at home Main Resort pool has been renovated this year and new water rides went down a treat. Thanks to Claire for organising accommodation and making it all so easy. See you next year #homefromhome

Date of stay:     Reviewer name: , Co down, Northern Ireland

Great Villa

My family loved your property and we will be returning to it, should it be available, great villa in a fantastic location, thank you so much for allowing my family and I to stay in your property!

Date of stay:     Reviewer name: , Glasgow

Rented both side by side homes!

Thank you very much! We had a wonderful time the villas were absolutely perfect - we will definitely be coming back to you again!

Date of stay:     Reviewer name: , Tyne and Wear

Fabulous Windsor Hills!

Just returned home after a lively stay at your villa on Windsor Hills! It was a beautiful home, clean and welcoming. We will definately be booking the same villa with you in two years time (if we had the money it would be sooner!). Thank you for allowing us to use your villa!

Date of stay:     Reviewer name: , Warrington, Cheshire

Great Holiday!

We had a great time in Orlando - thank you so much! As previously, the house was wonderful and all the arrangements / info you sent were spot on. We'll be back in touch again I'm sure.

Date of stay:     Reviewer name: , Gloucestershire

Fantastic Holiday

We had a fantastic holiday thanks. Villa was fab as usual (previously stayed here in 2014) and was just like being at home. We are starting to save for the next trip so will be in touch!

Date of stay:     Reviewer name: , Co down, N Ireland


We had a great time, thanks! The villa was great and ideally located (the main reason we chose this one).

Date of stay:     Reviewer name: , Isle of Wight


We honestly had the best holiday ever !! We really can't rate the villa enough, it was perfect thank you.

Date of stay:     Reviewer name: , Lancashire

Home from home

This is the second time that we have rented this villa and the house next door for our Family vacation. The villa is in a secure gated community with excellent facilities and is only 5 mins from the Disney parks. The house has everything that you would have at home and is in excellent condition. Just offf the 192 it has easy access to all routes and there is plenty of retaurants and shops in the surrounding area. We will have no hesitation in renting this villa again for our next visit to the Orlando Area. A Dream Home in a Dream Setting!

Date of stay:     Reviewer name: , Scotland UK

Perfect family villa

What a fabulous villa! Fabulous location, worth every penny. The villa itself was clean, spacious and the beds were so comfortable! Windsor Hills resort is so well maintained. We were only 5 mins from Animal Kingdom, 30 mins from Universal and the shopping malls and only 10 minutes to the supermarkets and good restaurants. I liked everything about the villa and the resort and I would definitely consider staying in the same villa at Windsor Hills again.

Date of stay:     Reviewer name: , Cheshire, UK

Perfect family vacation.

The house is immaculate. The pool area is extremely safe with an alarm for young children. So close to Disney. Close to Target and other shopping for groceries. Fully equipped kitchen. We just bought our own spices because we cooked a lot. Went over Thanksgiving. Game room perfect for children. Plenty of beach towels Washer and dryer in house. Great family vacation.

Date of stay:     Reviewer name: , Rochester, NY

Wish we had stayed longer!

We rented the neighbouring four bed homes, firstly can I say the villas were phenomenal. This has been the first villa I have stayed in that provided everything, even down to salt and pepper! The decor was beautiful and the home was clean and so well maintained, so a real credit to the owner and management company. In hindsight I wish we had stayed there for longer. When we return we will definitely be using that home again. It has been a pleasure dealing with you and look forward to doing so again in the future.

Date of stay:     Reviewer name: , Isle of Man

Excellent Place to Stay

Really good value for money house, great location for all the parks particularly Disney. The house is very clean, great facilities particularly the pool and the kitchen. The Windsor Hills complex is really safe, 24 hour manned gates for added security. Great place to stay. (I am very fussy and hard to please!! I was not disappointed in anyway at all). We will book this place again

Date of stay:     Reviewer name: , Kent, England

Duffy family holiday to Orlando July 2014.

Prior to arrival, we were given clear instructions to access the villa and accurate directions although we had previously stayed at Windsor Hills which made finding the accommodation easier. The villa was well maintained, modern and impeccably clean. There was plenty of information on surrounding parks, restaurants and amenities. The villa had everything to make our stay comfortable and enjoyable. Our children loved the themed bedrooms and we particularly enjoyed the jacuzzi! If you want to stay close to Disney, Windsor Hills is an excellent choice and we felt safe as it is a gated community. We would highly recommend this beautiful villa.

Date of stay:     Reviewer name: , Scotland

Excellent property very near to attractions

Excellent property on a great gated estate which is well looked after and secure. Property decorated to a high standard and very comfortable. Any minor problems we have had have been dealt with very quickly. We have stayed already twice and are going back again May 2015. I would recommend.

Date of stay:     Reviewer name: , England


We had an amazing time – thank you. We have been to Florida 6 times in the last 8 years, staying on Windsor Hills for the last four of those 6 times and your Villa is by far the best villa we’ve stayed in. Everything was perfect for us, the house itself is beautiful, the pool and Jacuzzi were awesome and we all felt very much at home and very comfortable there – making it very difficult for us to come home. You’ll be first on my list for a villa if we decide to return again next year. I filled in the visitors book with a glowing set of comments.

Date of stay:     Reviewer name: , Birmingham

Love Windsor Hills

Great, thanks Claire, just got back now. Very tired, loved the villa didn't want to leave!! We would definitely go back there! I was a bit freaked out by the spiders!! LOL!! I was blissfully unaware until I read the file! And then had one in the car! He he.... soon piled out until my hubby killed it! But holiday great it's the second time we have stayed at Windsor hills and loved it! Thanks so much best regards

Date of stay:     Reviewer name: , Cheshire

The icing on the cake!

What a fantastic villa! 10 mins to the Magic Kingdom and all the other Disney resorts, 25 mins to Universal and a steady 1hrs drive to Busch Gardens. So in terms of location you would definitely struggle to find anything better. Restaurants and places to eat were also close by and there is a lot of choice on the 192 (more than you could ever get through in your stay). If you fancy a night out without the car there is always the option of a taxi, pretty much anywhere up and down the 192 comes to less than $35 dollars for a return, so you can unwind with a glass or two of your favourite tipple if you want. The villa itself is beautiful, very practical with everything you could ever need but also very classy in decor. The pool and hot tub are great to take away all the aches and pains of a busy day at the theme parks while the games room can provide a haven for your children after they have had enough of Mum & Dad. The feel of the Windsor Hills resort is extremely nice and there is a fantastic communal pool that provides a bit more freedom for your children should you decide to have a day off from the parks. Security was a big concern of mine before travelling but Windsor Hills is the perfect place to stay if you want to forget about that. Security was very good and I am sure you would struggle to beat it anywhere else. All in all a fantastic villa, a superb location and for those security conscious among you a very safe environment.

Date of stay:     Reviewer name: , USA

Great Time

We have just returned from our Florida holiday at the Windsor Hill Resort and had a great time.

Date of stay:     Reviewer name: , West Cheshunt, UK

Oh God we had a LOVELY time!

The villa was amazing… everything we could possibly wish for… we are all feeling USA-sick – missing it all so much. Started saving for the next one. Windsor Hills was absolutely lovely – will definitely recommend anyone going to use you… Thank you so much for everything. We had a brilliant time.

Date of stay:     Reviewer name: , Portsmouth, UK

Wonderful Time in Florida

We wanted to thank you for helping us have such a wonderful time in Florida. It was our very 1st time there and having such a nice villa (and so close) was a huge factor in the whole experience. We would definitely consider going there again and if any friends enquire about such a holiday there for themselves, we will certainly be recommending you to book through. With very best wishes.

Date of stay:     Reviewer name: , Gloucestershire

Absolutely Fantastic Time

Hi Claire, Thank you for the deposit cheque return. Just wanted to say we had an absolutely fantastic time at the Villa, it is one of the best that we have stayed in. It was really comfortable, clean and the quality of the furnishings was very high. The location was great and I would definitely choose this villa again in the future. Thanks for all of your help with this reservation. Regards, Amanda

Date of stay:     Reviewer name: , Merseyside

Location, Location, Location!!!

Beautiful Villa in a superb location. Everything seemed to be just 5 mins away! Disney is just around the corner and plenty to do and see in the Windsor Hills resort itself. The Villa was clean and provided for everything you might need on your holiday. Will definately be visiting again.

Date of stay:     Reviewer name: , Slough, UK

We will be back!

Just to let you know that we had a fabulous holiday in the Villa at Windsor Hills, we are thinking of returning for a week in January 2011.

Date of stay:     Reviewer name: , Isle of Wight

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Thanks Claire, I had a great time! The location of the villa - about 10 mins from Disney and 5 mins from the supermarket is a massive bonus!

Date of stay: March 2024    Reviewer name: J Hampson, Wrexham