A superb example of a private luxury villa offering one-level living and private pool. Located within the renowned Windsor Hills, a secure gated resort with outstanding guest facilities and clubhouse and one of the finest locations close to Walt Disney World - 5 minutes away. At 1,816 sq ft - this executive 4 bedroom home offers the touch of luxury and amenities second to none - including all ensuite bedrooms, 32 inch TV's in all bedrooms, bonus games room equipped with SNES console and free WIFI. Two children's bedroom's are Disney and Princess themed with the remainder of the home presented in elegant contemporary decor. Guests are welcome to venture onto Windsor Hills community to visit the clubhouse for a game of table tennis, try a movie at the onsite 50-seat cinema or take the kids to the play area for an afternoon.
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.
Upon entering the property you are presented with the spacious living area styled impeccably with natural contemporary decor, leading on to blend effortlessly with the open-plan diner and kitchen space to the rear of the property. The living room offers a large modular double-ended leather sofa and matching armchair, ornate coffee table and wide cherry wood media unit with speaker system and wall hung 52" flat screen tv.
The sizeable kitchen area is beautifully appointed with granite countertops, stunning wood cabinatry and upscale stainless steel appliances - fully equipped for catering for a large family or group. Additional bar stool seating for 4 provides a very sociable space for simultaneous cooking and entertaining. The converted garage hosts a utility area - with washer and dryer.
The villa benefits from 2 family eating zones - the breakfast nook has a dual aspect view of the pool area and has a modern table and chair setting for 4 - ideal for early morning coffee and read of the paper. A further formal dining space, again facing the pool with access outside hosts an opulent 6 seater dining table and stunning dark wood furnishings with wall art to define the space. Perfect for intimate family dinners.
The Master Bedroom's soft gold interior offers a relaxing and luxurious space with views and door access to the pool area, King Size Pillow Top Bed, dark wood furnishings and double wardrobe. There is a wall hung 32" flat screen TV and ensuite double shower room for guests.
The 2nd Master Bedroom situated at the front of the property is an inviting, restful room with gentle coffee coloured soft furnishings and King Size wrought iron Bed. There is a 32" wall hung flat screen TV and ensuite with shower over bath arrangement.
The 3rd Bedroom is a bright and fun Disney / Mickey Mouse themed twin room - perfect for younger children and offers a 32" wall hung TV and walk in double shower ensuite.
The 4th Bedroom - is a pretty Princess themed twin room - again wonderful for little ones and capturing their imagination! Ornate ivory wood furnishings dress the room along with a 32" TV and ensuite bathroom with shower over bath arrangement.
The games area features a lounging zone with flat screen TV and SNES games console, table and seating for 2, air hockey and table foosball. This is a perfect family spot for some noisy and competitive gaming before and after dinner!
Outside the pool styled in a contemporary curved design with raised spa and surrounding paver-brick sun decking is a superb spot for a swim with the children or relax in the spa. Under the large covered lanai guests can enjoy waterside alfresco dining at the table with seating for 6. There are also comfortable sun loungers available to recline, relax and take in the Orlando sun rays!
FREE use of the in home wireless internet.
Baby Equipment can be hired locally.
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. A cleaning fee is added to any booking under 7 nights.
Have you stayed here? Share your thoughts –
write a review
Villa was Terrific!
Stayed at this villa in Windsor Hills. Arranged by Claire and she kept us updated all the way through from our booking last year to our holiday in Windsor Hills Resort this month. Villa was perfect for a family of 6 (4 adults and 2 children). Great facilities in villa with games available for the days we didn't go to the parks as well as the jacuzzi and pool. Windsor Hills faclities are also great with the clubhouse and terrific pools and slides.. Really great prices for food/drinks/pool toys etc... 5 mins from Disney World and all the magic of the parks. Really well organised and would recommend Claire and her company to anyone looking for a great holiday in Florida.
Date of stay: July 2023
Reviewer name: Hailey Family, Glasgow
We have just returned from an amazing family holiday to Florida and cannot thank Claire enough. Excellent, swift communication regarding our booking from start to finish. Lots of helpful information, including sourcing reasonable car hire. The villa was fantastic, well located for all parks and provided everything we needed. We would highly recommend Claire and will definitely use again for any future booking.
Date of stay: October 2022
Reviewer name: Gee Family, Longfield, Kent
We had a wonderful experience in Orlando with the help and arrangements from Claire. Everything was wonderful from start to finish and Claire was amazing throughout. Highly recommend and will definitely be using again. Thank you again Claire.
Date of stay: August 2022
Reviewer name: McGurk Family, Essex
Just got back from Florida after spending 28 days on holiday. Stayed at Windsor Hills resort in this 4 bedroom villa and we were very impressed! Pool was lovely and warm, the villa was just perfect could not fault it one bit. Thank you to Claire for keeping in touch throughout the journey of booking the villa up until now you have been amazing! We would definitely stay again! Thank you!
Date of stay: December 2019
Reviewer name: Bayford Family, West Wickham, Kent
Always brilliant, fast and easy to communicate with, We have used these villas several times now, and they are always absolutely stunning, as described, and never had any trouble. Will always come back to using this company in the future! We had a fantastic holiday!
Date of stay: October 2019
Reviewer name: Mills Family, West Sussex
Home from Home
We have just stayed in the same villa for the third time in Windsor Hills. Each time we have booked through Claire. She has been very efficient and helpful. Our villa really does feel like home from home. Would def recommend Claire. Thank you.
Date of stay: June 2019
Reviewer name: Morrow Family, Hillsborough
We had a most enjoyable stay. Beautiful, immaculate house. Ideal location.
Date of stay: March 2019
Reviewer name: Reid Family, Ayrshire, Scotland
We had a lovely holiday and villa was perfect!
Date of stay: October 2018
Reviewer name: Webster Family, Aberdeenshire
The holiday was brilliant and the villa was great, we didn’t want to come home. We are looking to return next August!
Date of stay: March 2018
Reviewer name: Bishop Family, St Helens
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: October 2017
Reviewer name: Thompson Family, Tyne and Wear
Home a week or two now! Just getting over the jet-lag! I wanted to say thank you so much for a wonderful stay. The house was perfect and we really enjoyed our holiday. We will absolutely contact you again the next time we go to Orlando.
Date of stay: July 2017
Reviewer name: McCartan Family, Co.Meath, Ireland
We had a fabulous holiday, thank you!
Date of stay: July 2017
Reviewer name: Millard Family, Rochford, Essex
Thank you, we had an amazing holiday. The villa was brilliant and really felt like home from home after having been before (previously stayed here in 2014). We really hope to visit again soon. Thanks for organising it for us.
Date of stay: June 2017
Reviewer name: Marrow Family, Co down, N Ireland
The villa was amazing, absolutely loved it didn't want to come home!
Date of stay: April 2017
Reviewer name: Connah Family, Barnsley
Fantastic is the best word to describe this villa which has everything a family would require in a holiday villa. The villa was spotlessly clean. The Windsor Hills location and security is superb. Special mention for Claire who was excellent to deal with in every way with the rental process. The owners from Canada are also very kind people. I highly recommend staying here, we would love to go back and will be telling friends and family how good our stay was.
Date of stay: October 2016
Reviewer name: Forrest Family , Aberdeen Scotland
Thank you. We had a brilliant time and the villa was lovely!
Date of stay: July 2016
Reviewer name: Roberts Family, Merseyside
Everything was Brilliant
We had a fantastic time and loved the villa, the pool (I especially appreciate the pool heating!) and the location.
Date of stay: March 2016
Reviewer name: Balaam Family, Middlesex
Home From Home
This is our second time that we have rented this villa and the next door house for our family vacation. The villa is in a secure gated community with excellent facilities and only 5 minutes from the Disney parks. The house has everything that you would have at home and is in excellent condition. Just of the 192 it is easy access to all routes and their is plenty of restuarants and shops in the area. We will have no hesitation booking this again on our return to the Orlando Area . A Dream Home in a dream setting !
Date of stay: October 2015
Reviewer name: The Harkins Family, Scotland UK
We had a lovely time...sad to be home! The villa was perfect, thanks!
Date of stay: June 2015
Reviewer name: Chadwick Family, Wigan
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: October 2014
Reviewer name: Beech Family, Isle of Man
Lovely villa at Windsor Hills
Stayed at this villa for a week in October 2014, without a doubt the nicest villa we have stayed in. The children were delighted with the themed bedrooms and the villa had everything you needed for a comfortable stay. The pool and spa were brilliant and the pool heating was very efficient making for a lovely pleasant evening swim after a busy day at Disney. Would not hesitate to recommend this villa - very clean, well maintained and with high quality furniture.
Date of stay: October 2014
Reviewer name: Pedge family, England
Thank you for letting us stay in this amazing villa, it was more than we expected. Very well equipped and a perfect location. WE WILL BE BACK :-) and more than happy to recommend to our friends and family. Thank you again, we will be in touch when we plan our next visit.
Date of stay: May 2012
Reviewer name: Goody Family, Milton Keynes
Hello, we had a fabulous time in Florida and look forward to going again! Thanks
Date of stay: September 2011
Reviewer name: Blenkinsop Family, Hartlepool
Many thanks Claire, We had a fantastic holiday and thoroughly enjoyed staying at the villa - the facilities, and condition, were excellent. I would certainly recommend staying there to others.
Date of stay: March 2011
Reviewer name: Neil, Glasgow
The villa was superb!
Good morning Claire. Back home on Saturday morning after a great holiday in Florida. The villa was superb, everything we could have wished for. Very comfortable and very well fitted out. If we hadn't been at the parks every day we could have happily sat around and in the pool. We have friends planning trips next year and we will have no hesitation in recommending the villa to them. Thanks again for all your assistance in arranging the accommodation and who knows, if the funds allow, we may repeat at some time in the future! Kindest regards and every best wish for the future.
Date of stay: October 2010
Reviewer name: Marsh Family, Dundee
Thank you for sending back our refundable deposit. We had a wonderful holiday and the Villa was everything and more. I will take your cards into work when term time starts back. Thanks again for all your help.
Date of stay: July 2010
Reviewer name: Diane, Stonehaven, Aberdeenshire
Just to let you know that the villa was superb and we all had a great holiday. Thanks for all your help with the booking.
Date of stay: May 2010
Reviewer name: Tajinder, Berkshire
Fantastic, Superb, Fab
Just wanted to drop you a line to let you know how much we loved the villa.
It was fantastic! We had such an amazing time. The villa is in a superb location on Windsor Hills and Windsor Hills itself is also in a great location for everything. The communal swimming pool is fab!
The villa had everything we needed and more and everything was pristine!
We wouldn't hesitate to return to this villa next time we plan a trip to Orlando and we have already recommended it to some friends. We will continue to recommend it to anyone that mentions a trip to Disney.
Thanks again for such a great service.
Date of stay: May 2010
Reviewer name: Nicola Moore, Luton
How to be Happy
"If they're not happy we're not happy" is the motto my wife I adapt as we approach our vacation stay. I can proudly say "they were happy". Windsor hills provided a well balanced blend of fun activities for our kids and relaxation for the adults. The directions and instructions were easy to follow and we were able to find the property without a headache. The property was clean and well maintained throughout our stay. My family was delighted that we were able to comfortably plan our meals, cook when we wanted or go out dinning nearby. The pool, the pool, the pool was the highlight for the kids, movies and the game room delightfully kept the kids happy, wet and occupied. I would recommend a stay and recommend a revisit especially if you want to be happy on your vacation stay.
Date of stay: August 2009
Reviewer name: Robert M, New York