Entire home

Welcome to The Windsor Dream!

Family-friendly villa with fitness centre and Hot tub

Photo gallery for Welcome to The Windsor Dream!

Professional Arcade Room - All Free Play
Dual Racing Games
Professional Air Hockey
Immersive Transformers Game
Dual Players vs. The Decepticons

Reviews

10 out of 10
Exceptional
5 bedrooms5 bathroomsSleeps 122800 sq ft

Popular amenities

  • Dryer
  • Washer
  • Barbecue grill
  • Outdoor space
  • Air conditioning

Explore the area

View in a map
  • Place, Mystic Dunes Golf Club
  • Place, Disney's Animal Kingdom® Theme Park
  • Place, Disney's Hollywood Studios®
  • Airport, Orlando, FL (MCO-Orlando Intl.)

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

Bedroom 5

2 Single Beds

5 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden

About this property

Welcome to The Windsor Dream!

Welcome to The Windsor Dream! We recently upgraded our game room to a professional arcade room. We have game rooms in some of our other homes. In this home it is a professional arcade with games you might find at Dave & Busters or Chuck-E-Cheese. We have an NBA basketball shooting game, Skee-Ball like you may have played at a seaside boardwalk arcade, and two Super Bike motorcycle racing games. You can play individually or go head-to-head in two player mode. We have an immersive Transformers game where two players sit inside the gaming cabinet to defeat the Decepticons together. We have a multi-cade system that has all of the classic arcade games from the 1980s on one machine, such as Pac-Man, Ms Pac-Man, Galaga, Donkey Kong, Frogger, Space Invaders, and more. Finally, we have an 8 foot long professional air hockey table. The best part? All of these games are set to "free play" for our guests - no quarters needed! Our arcade room has been completely finished and insulated, and the garage doors removed, so it is a true "room". It also has its own dedicated air conditioning system, making it quite cool - even in the warmer months.

In addition to looking at our Five Star reviews for The Windsor Dream, we invite all families considering our home to look at our reviews for our properties right next door at VRBO listing #840075, #93534, and #2548198. We are blessed to have received over 550 Five Star reviews across our homes, more than any other owner in Windsor Hills.

Discover Windsor Hills at The Windsor Dream. Bill and Donna's luxury villa at Windsor Hills, featuring a true south-facing private pool and hot-tub, with no rear neighbors. We are one of the closest homes to the amazing Windsor Hills Water Park and Clubhouse, about a 2 minute stroll away.

We own FIVE HOMES in Windsor Hills – Four of them are side-by-side: The Windsor Dream, The Windsor Magic, The Windsor Fantasy, and The Windsor Wonder, plus another home around the corner – The Windsor Treasure - so if you are traveling with friends or extended family please just let us know.

* Private South-Facing Pool, with No Rear Neighbors. Corner lot for even more privacy.
* South-Facing Pools get the most sun all day.
* Only 2.5 miles away from Disney. The closest resort that is not an actual Disney hotel.
* One of the closest homes to the amazing Windsor Hills water park - just a 2 minute stroll away.
* NO FEES for our guests to utilize the water park.
* Enhanced COVID-19 cleaning procedures in place.
* Contactless check-in via a personalized code for our electronic lock.

There are NO FEES for our guests to utilize the Water Park or Community Pool. We will provide the names of your family members to the Windsor Hills staff so there will be no cost for you. For all non-registered guests, the wristbands cost $10 per person per day, but again that will be waived for your family.

The most important feature of our family retreat is that we offer one of the few south-facing pool homes in Windsor Hills that also has no rear neighbors. Spend a moment viewing the Windsor Hills development on an aerial map. Most of the south-facing homes back right up to another property. Most of the other homes with no rear neighbors face north, east, or west – limiting the amount of sun the pool area will receive. If you select a home that has rear neighbors, the neighbors pool will be approximately 10 feet from your pool – not my idea of relaxing! Take a look at the view from our pool area and you will see the difference.

Our home has 5 bedrooms, each with a private en-suite bathroom. Every bedroom has its own flat-panel television.

You will also have access to all of the amenities at Windsor Hills for no additional cost. Windsor Hills has an amazing zero-entry community pool, a large water park for the children, a basketball court, tennis courts, volleyball court, ping pong tables and a putting green. We also provide our guests access to the Windsor Hills Fitness Center, which offers multiple cardio machines as well as weight/resistance training.

Windsor Hills is the closest resort to Disney that is not an actual Disney hotel. Our home is only 2.5 miles from the main Disney gates, so it takes us about 6 minutes to get from our home to the Animal Kingdom. We are also right next door to the award winning Mystic Dunes Golf Course. Some resorts advertise that they are just "miles to Disney", but that can still be a very long drive. We are only 2.5 miles away, but it still takes 6 minutes to get to Disney. For resorts that are 10 miles away, it can sometimes take 30-40 minutes (each way) depending on the Orlando traffic on that particular day.

We are available by both phone and e-mail during your stay, and we have a local caretaker who lives 15 minutes away available 7 days a week should you need any assistance during your stay.

Please note: The Windsor Hills waterpark will be closed for renovations between January 5th, 2026 and February 6, 2026 (approximate dates). The community pool and hot tub will remain open.

*** Any data or information below this line has been auto-generated by the listing website and may not be accurate. Please ask us if you have any questions. Thank you! ***
Our prices include all fees. No hidden fees.

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Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Once your reservation has been confirmed we will forward to you a copy of our Guest Registration Form for your electronic signature.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number DWE5914079
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

We should mention

A car is recommended for transport to and from this property

About the area

Kissimmee

Windsor Hills, a neighbourhood in Kissimmee, is home to this villa. Mystic Dunes Golf Club and Reunion Resort Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Old Town. Travelling with kids? Make time for Disney's Hollywood Studios®, or head to an event or a match at ESPN Wide World of Sports Complex. Spend some time exploring the area's activities, including golfing.
Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 20 min walk - 1.7 km
  • Disney's Animal Kingdom® Theme Park - 7 min drive - 4.8 km
  • Disney's Blizzard Beach Water Park - 8 min drive - 7.2 km
  • ESPN Wide World of Sports Complex - 8 min drive - 7.1 km
  • Disney's Hollywood Studios® - 9 min drive - 8.5 km

Getting around

  • Kissimmee Station - 37 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 31 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪Drafts Sports Bar & Grill - ‬14 min walk
  • ‪Sickies Garage Burgers & Brews - ‬3 min drive

Frequently asked questions

Does Welcome to The Windsor Dream! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Welcome to The Windsor Dream! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Welcome to The Windsor Dream!?

Check-in begins at 4:00 PM.

What time is check-out at Welcome to The Windsor Dream!?

Checkout is at 10:00 AM.

Where is Welcome to The Windsor Dream! located?

This family-friendly Kissimmee villa is located in Windsor Hills, within 3 mi (5 km) of Mystic Dunes Golf Club and Island H2O Live!. Walt Disney World® Resort and Old Town are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 161 out of 164 reviews
Rating 8 - Good. 2 out of 164 reviews
Rating 6 - Okay. 1 out of 164 reviews
Rating 4 - Poor. 0 out of 164 reviews
Rating 2 - Terrible. 0 out of 164 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Jason T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home, nice location.
Stayed 7 nights in Aug 2025

10/10 Excellent

Jennifer A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay

Great property, ideal location and great communications from the property owner. Would not hesitate to stay again or recommend to family and friends
Stayed 15 nights in Oct 2022

10/10 Excellent

Ashley E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for families

Property is in a perfect location, has an excellent pool and a safe gated community. It is also very clean and property owners were easy to work with.
Stayed 6 nights in Jan 2022

10/10 Excellent

Mom c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Home Away From Home!

This house was perfect for our family! It was very clean, roomy, close to theme parks and grocery stores. Grandchildren loved the private pool and pool table. We would definitely stay again!
Stayed 6 nights in Jun 2023

10/10 Excellent

Victoria S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful home and owners!

The house was the absolute best! The owners, Bill and Donna, were the best! Would 100% recommend their properties to others and out entire family would love to return.
Stayed 4 nights in Feb 2022

10/10 Excellent

JAY P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Orlando 2023

Great Place to stay!!!!! Owner was always accommodating!!! SUPER NICE PEOPLE!!!!!!
Stayed 8 nights in Jul 2023

10/10 Excellent

Edmund O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome place, delightful spot!

What a wonderful home to rent! We had a blast. The home is large and comfortable, close to disney, and super easy to find. Security gate was well staffed and welcoming. The bedrooms were spacious and we loved the pool. We will be back!
Stayed 4 nights in May 2021

10/10 Excellent

sharon m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation feb 2021

Great location! Had a great staycation with grandchildren around warm private pool and hot tub. Great children's castle playground. Owners super easy to work with. Great communication. Beautiful home!
Stayed 9 nights in Jan 2021

10/10 Excellent

Wage W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Beautiful, clean home with plenty of room for our family of eight. The pool was clean and warm. We enjoyed the hot tub many nights after a long day at the park. The double washer/dryer was a plus. The communication with the owner was the best we have had in the 22 years of staying at various homes in Florida. We we definitely stay here again.
Stayed 7 nights in Oct 2021

10/10 Excellent

Barbe R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Windsor Dream was a Dream

Our stay was great at Windsor Dream! Bill and Donna were very responsive to what ever we needed. The house was everything we needed and very close to the theme parks and shopping- which was over the top for our family of 9! We would rent this property again. Thank you for making this a great experience and memory for us!
Stayed 10 nights in Nov 2021

10/10 Excellent

Steven S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent

The house is perfect for our family with 12 members. The right amount of space. The neighborhood is well maintained, and clubhouse pool was awesome for our young children to play in. Communication was great with the host, and efficient organized process.
Stayed 5 nights in Apr 2022

10/10 Excellent

Nancy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

We had a wonderful vacation at the Windsor Dream! The accuracy of the property description was spot- on and Donna and Bill responded quickly to any questions I had. The location of the resort was ideal for any of the Disney attractions and was only a short drive to Universal attractions. The pool was a wonderful way to relax after a long day at a park! Thank you Donna and Bill for being great hosts! We look forward to our next vacation. Nancy
Stayed 6 nights in Jun 2023

10/10 Excellent

Karen W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!!

We really enjoyed our stay at this property. We have stayed in many homes in Windsor Hills and this ranks right up there with the best. Home was very clean, well stocked, beds very comfortable. Pool and hot tub were wonderful. Nice to not back up to any rear neighbors. Home is also decorated beautifully and has comfortable furniture. We loved the arcade in the game room and had some fun competitions. Also the multiple washing machines/dryers were great to have. Communication with Bill was A+. All in all a great trip! Thanks! We'd love to come back!
Stayed 8 nights in Jun 2019
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Donna H.

Perfect Vacation Home for my Family of 10

My family (6 adults, 4 children) really enjoyed our stay in this BEAUTIFUL home! Everything we could have wanted was in this house and each bedroom having its own bathroom was really a plus. It was very clean, full of amenities and had hosts, Bill and Donna, who were fantastic. They were available to answer any questions we had and also sent us ideas for places they thought our grandchildren would enjoy. In advance of arrival, they even sent us an app that we could download on our phones that told us all about Windsor Hills, their house, restaurants and surrounding things to do in the area. The game room and "heated" pool were a big hit with both the kids and adults. Lots of time was spent in the game room with lots of basketball competition between the adults. Resort also had a big pool and slides for the kids, along with many other amenities, which were lots of fun. Windsor Hills was amazing, and I can't say enough about the hosts for The Windsor Dream, Bill and Donna. I highly recommend this place and would not hesitate to return again.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Lynn B.

Great Location, Great Amenities

This location was extremely convenient for doing Disney World. The homes (we rented both of the side-by-side homes as there were 19 in our group) have bathrooms with each bedroom making it a great choice for larger groups. The game rooms set up in the garages were a favorite of the young children and even some of the older ones. The owners are very attentive to the detail of their units and followed up with us both before and during our visit. Any issues encountered during the stay were immediately addressed by the maintenance person who lives in the same community. Our family would highly recommend this owner's rentals based on our experience and the quality of the homes and amenities provided.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Art T., Newark,De

Beautiful House and Great Location

My wife and I, our two daughters, their husbands and four children spent seven days at this very spacious home. Ten people and it never seem crowded, The bedrooms were very well appointed with very comfortable beds. The pool with its great location was warm all day and was very inviting after a long day at Disney, which is only 2 miles away. The HE(2) washers and (2) dryers were a god sent to do laundry before heading home. The game room was great for the kids. The Windsor Hill Resort is close to everything. The whole family was very happy with the house. Lastly, but most important was the attentiveness of the owner Bill. He always answer our e-mail promptly. I would definitely without hesitation recommend this house to my friends and family. My youngest daughter said she wants to come back in May for her 40th. Maybe we will see you again, Thanks Again Bill and Donna

10/10 Excellent

Darrin W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Stay!

We've stayed in Windsor Hills several times as our family loves the location and the gated community. This was amazing and Bill and Donna were far and away the best hosts we have had! Everything in the home was as described. Bill and Donna went out of there way to ensure we knew every detail about the house prior to arrival and even checked on us several times throughout the stay. We never had to reach out to ask questions - they made sure and addressed every possible question from the start and they made the check in process extremely easy. There were a few cold days when we were in Orlando, but the upgraded pool heater that Bill and Donna recently installed kept the tub Hot - and the kids loved the pool! The kitchen had all the items you would need for an extended stay - and any groceries or personal items you need can easily be picked up nearby at Wal Mart or Target. There were eight of us in the house and we all had plenty of space. Our family cannot give a high enough review - this is the house you should book if you are looking to visit Orlando!
Stayed 8 nights in Dec 2020

10/10 Excellent

Jennifer M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Getaway

We had a great experience renting Bill and Donna’s house to go to Disney World with family and friends. It is close to the parks which is key because the traffic is heavy in Orlando. The house is just as described it is beautiful and clean and has everything you need and want. It is also in a gated community which we wanted. The pool is south facing which is perfect to get sun all day and heated so it is warm and the hot tub is perfect after a long day at the parks. There is also a club house with a large pool and playground/water slides snack bar/store that is walking distance from house. The kitchen is well equipped with everything you need and even has a gas grill outside to barbecue. The bedrooms are decorated beautifully and some have Disney/universal themes and the beds are very comfortable. We enjoyed using the game room at night playing pool and video games. Bill and Donna are very nice and attentive and although we didn’t need them for anything during our stay they checked in frequently to make sure we were doing okay and also gave us recommendations of places to shop, eat and activities they thought we may enjoy. We will definitely be back and stay here again! Jen M
Stayed 5 nights in Feb 2023

10/10 Excellent

Mark R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation home

Beautiful home, close to basically everything, pool was great, kids loved the game room, would visit again
Stayed 7 nights in Jun 2025

10/10 Excellent

Corey W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house in a great location

Beautiful home! Very clean and well stocked kitchen (pots, pans, dishes & utensils). House was very easy to find from the security gate. Good communication with the hosts Bill & Donna. They even gave us recommendations for restaurants and entertainment. The game room was a hit with the kids ages 4-10. I even shot a few hoops. The pool/spa area was perfect for our family of 12. The two washers and dryers was a plus for a big family. I would definitely recommend this rental. We'll be back!
Stayed 5 nights in Jun 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kym S.

We had a great time!

This is the second time we have stayed at Bill and Donna’s rental and we have loved it both times! The emails and communication leading up to our trip were incredibly informative and helpful. The home was in wonderful shape and we especially enjoyed the added arcade games. The walk to the shared pool and water slides is very close, however, we really enjoyed lounging in the pool at the house the most! We will plan to book here in the future.

10/10 Excellent

Chris A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Disney Magic

This is an amazing spot for any family looking to combine Disney fun with a relaxing (away from the Disney) location. It's about a 15 minute drive to all the parks. The house is wonderful, clean, and exactly as advertised. The kids loved the game room and private pool. As a bonus the community pool is beautiful as well and the staff at the clubhouse were kind and helpful. Would absolutely book again.
Stayed 4 nights in Apr 2025

10/10 Excellent

Vitaliyd12 D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Orlando vacation house

We have tried very many vacation homes and had good and bad experiences. But Bill and Donna by far have been the best hosts we ever had. And their house was one of the best we ever stayed at. Thank you Bill and Donna!
Stayed 6 nights in Feb 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Anh L.

Perfect stay at a beautiful home !

Bill and Donna are amazing hosts and have made our stay so comfortable. They have such passion in their homes and aim for satisfaction from those who stay in their homes. During the process of booking, before our trip and during the trip... they were always touching base to ensure are stay was comfortable and enjoyable. They made suggestions on where to go and where to eat.. it was so pleasant to hear from them. Their home is immaculate with so much ample space. It was only the 4 of us.. but the home can fit another family of 4 comfortably. It had all the needs and well labeled. Information package/app provided was so handy for us! This will be our go to home when we come back.. will be renting from Bill and Donna again! Thank you so much for accommodating us and making our first trip to Orlando so enjoyable! Anh and John

10/10 Excellent

Amanda R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A home away from home

Bill and Donna thought of everything with this property! Our family of 7 enjoyed this home away from home for a week during the Christmas season. The home is absolutely beautiful, very well decorated, and maintained. The kitchen had everything you needed to cook, grill, bake, etc and they provided starter supplies of toiletries and paper products. They provided plenty of towels for showering and also for the pool, and also had a well stocked linen closet. The game room provided endless hours of fun for everyone! We also enjoyed many hours in pool and hot tub as well. The neighborhood is very beautiful and quiet and our neighbors were all very respectful. The property is in the perfect location and is a very short drive to restaurants, stores, gas stations and attractions. We also have family not far from the home and were able to visit the easily. Bill and Donna were very easy to reach and communicated with us regularly throughout our stay. They are very thoughtful and personable hosts. We loved this home very much and definitely look forward to staying here or in any of Bill and Donna’s homes in the future!
Stayed 7 nights in Dec 2024

About the host

Hosted by Bill and Donna

Host profile image
Donna and I have been married for 30 years, and we have been blessed with 5 children, so we have many years left to enjoy the magic of Disney!

We fell in love with Windsor Hills since we are only 2.5 miles away from Disney, and very close to Universal Studios too. We also take time to travel to either coast to swim in the ocean as a day trip (just 1-2 hours away). We just love our location.

Why they chose this property

We rented many homes in Windsor Hills before purchasing our home. Our home backs up to the green conservation area, where no new homes can be built. This means when we are relaxing in our private pool, there are no other families behind us looking into our pool area. If you look at photos of other homes, you will see how close together the homes are - all back-to-back. In addition, since our home is on the end of our "row", the neighbors to the side are also a greater distance away. In our opinion our home is the most private in all of Windsor Hills.

What makes this property unique

Spend a moment viewing the Windsor Hills development on an aerial map. Most of the homes face north, east, or west – limiting the amount of sun the pool area will receive. When you view the aerial map, you'll see many of those pool areas covered in shade - even during the middle of the day. With our south-facing pool, the sun is always on our pool area.

Premier Host

They consistently provide great experiences for their guests