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 30 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
Update Janauary 2019: Just opened (late 2018) the Windsor Hills Resort clubhouse now has a Brand New Water park. Featuring water slides and a splash park for kids. This is a fantastic addtion to the Orlando resort and we know guests are going to love it. We will be adding more information and photos and the new water park very shortly.
Update September 2019: Please see the video below which shows the new Windsor Hills Resort water slides and splash pad. This was opened late 2018 and we already know guests are loving it!
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.
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.
Rental rates quoted in
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.
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A Magical Stay at Windsor Hills Resort
My family and I recently had the pleasure of staying at a villa in Windsor Hills Resort in Florida, and I must say, it was a truly magical experience. From the moment we arrived, we were greeted with warm hospitality and exceptional service, thanks in large part to Claire at Villas in Florida 2 Rent. Claire's dedication to ensuring our stay was perfect was evident from the start. Her prompt and friendly communication made the booking process a breeze, and she went above and beyond to accommodate our needs. She provided us with all the information we needed, from detailed directions to the villa to recommendations for nearby attractions and dining options. Claire's attention to detail and commitment to guest satisfaction made us feel truly valued. She was always just a phone call or message away, ready to assist us with any questions or requests. Her professionalism and genuine care for her guests were a standout feature of our experience. The villa itself was nothing short of fantastic. Spacious, clean, and beautifully decorated, it immediately felt like a home away from home. The fully equipped kitchen allowed us to prepare meals when we wanted, and the living area was perfect for relaxation after a long day at the parks. The bedrooms were comfortable and well-appointed, ensuring a restful night's sleep. One of the highlights was the private pool and screened lanai area, which provided a peaceful oasis for morning coffee and evening swims. The villa exceeded our expectations in every way. Windsor Hills Resort's location is a dream come true for Disney enthusiasts. It's just a short drive away from the Disney parks, which meant we could maximize our time in the parks without long commutes. Additionally, the resort is conveniently located near the bustling Highway 192, offering a plethora of dining and entertainment options. We enjoyed exploring the nearby restaurants and shops, adding even more convenience to our stay. Our stay at Windsor Hills Resort was an unforgettable experience, and a significant part of that can be attributed to Claire's outstanding service. Her dedication and professionalism set the tone for a perfect vacation. The villa itself was a cozy retreat, and its proximity to the Disney parks and the 192 made our trip even more enjoyable. I can wholeheartedly recommend Windsor Hills Resort and the services of Claire at Villas in Florida 2 Rent for an exceptional vacation experience. We can't wait to return for another magical stay. Thank you, Claire, and the entire team, for making our family's Disney vacation truly special.
Date of stay: July 2023
Reviewer name: Thorpe Family, Coventry
Great location and proximity to Disney world and the pool and splash pad were perfect for the kids!
Date of stay: October 2021
Reviewer name: LeGrand Family, USA
Beautiful townhouse we enjoyed it ,very well kept, excellent communication with management, 5 stars I will definitely stay again!
Date of stay: July 2021
Reviewer name: Darius, USA
Everything was great!
Date of stay: July 2021
Reviewer name: Maria, USA
Thank you for providing us with clean and comfortable rooms. Wal-Mart is next to the resort area. The location is very convenient, allowing us to spend an unforgettable holiday life.
Date of stay: June 2021
Reviewer name: Rong, USA
I loved it.... a lot for the kids to do and I will be staying there again really soon!
Date of stay: May 2021
Reviewer name: Anthony, USA