Welcome to The Windsor Dream!

Kissimmee, Florida
$423 avg/night Minimum Stay 2 Nights
Bed 5

Bed

Bath 5

Bath

Home Villa

Property Type

Sleep 12

Max Sleeps

Night 2 nights

Min Stay

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! ***

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2800 Sq Ft (260 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Barbecue Grill Garden Patio
  • POOL/SPA

    Heated Pool Hot Tub Private Pool Shared/communal Pool
  • BATHROOMS

    5 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • THINGS TO DO

    Bicycle On Site Fitness Center Golf Nearby Golfing On Site Kayak On Site Tennis On Site
  • ENTERTAINMENT

    Arcade/game Room Games Pool Or Billiards Table Video Games Video Library TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Derek T.

    Submitted Jan 4, 2026

    Stayed Dec 30, 2025

    The hosts did an amazing job ensuring our stay was great…even sending chemical to keep the pool warm when temperatures dropped unexpectedly to 40 degrees overnight. Make sure to pack/buy small needs such as coffee filters, spices, garbage bags, soap, etc. because those items were not sufficient for our stay. That said, everything about the home, the game room, the appliances, kitchenware, and the pool were awesome. Great place to stay for a family!

  • Craig B.

    Submitted Dec 28, 2025

    Stayed Dec 19, 2025

    We loved our stay at Windsor Dream! Bill and Donna were so easy to communicate with and super accommodating. Their were nine of us (two families) staying there with kids ages ranging from 5-12. There was plenty of room for everyone and the kids were either in the private pool or the amazing arcade most of the time. Us parents were able to just relax while the kids played safely in our rental. The community pool and clubhouse was a quick walk away from our rental and there were so many free activities for the kids to do every day (pool side games, arts/crafts, movies). The market store at the clubhouse was super clutch, they serve great food, drinks, and they also have some basic grocery needs. I highly recommend Windsor Dream or any other unit Bill and Donna owns, because they provide the best guest experience I've ever had.

  • Lisa S.

    Submitted Dec 18, 2025

    Stayed Nov 22, 2025

    This is a unicorn house! A true unobstructed south facing pool that is actually heated and a hot tub that is hot! I have been renting houses for decades and have been disappointed countless times, but not this time! The kitchen is insanely well-stocked with all the things that you would expect and many that you would not (hello cookie sheets) The games room is as pictured and my grandkids loved it. The location is perfect for the parks and the Walmart is super-close for all your grocery needs.The owners are very responsive and we had no issues. We would happily rent this house again!

  • Kristen B.

    Submitted Dec 11, 2025

    Stayed Nov 16, 2025

    We had a wonderful time at Windsor Dream! Great location for all the parks. We enjoyed the home pool as well as the complex pool. Very friendly responsive owners and the game room was a fun addition. Would highly recommend this property for an extended family.

  • Jason T.

    Submitted Aug 10, 2025

    Stayed Aug 2, 2025

    Wonderful home, nice location.

  • Mark R.

    Submitted Jul 7, 2025

    Stayed Jun 28, 2025

    Beautiful home, close to basically everything, pool was great, kids loved the game room, would visit again

  • Corey W.

    Submitted Jun 21, 2025

    Stayed Jun 12, 2025

    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!

  • Kym S.

    Submitted Jun 8, 2025

    Stayed Mar 1, 2025

    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.

  • Chris A.

    Submitted Apr 23, 2025

    Stayed Apr 18, 2025

    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.

  • Donna H.

    Submitted Mar 4, 2025

    Stayed Feb 17, 2025

    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.

  • Vitaliyd12 D.

    Submitted Feb 22, 2025

    Stayed Feb 2, 2025

    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!

  • Anh L.

    Submitted Feb 8, 2025

    Stayed Jan 22, 2025

    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

  • Amanda R.

    Submitted Jan 10, 2025

    Stayed Dec 18, 2024

    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!

  • Sarah w.

    Submitted Sep 8, 2024

    Stayed Aug 20, 2024

    The villa was very clean when we arrived and exactly as it looked on the photos. The location was perfect, close to restaurants and the supermarkets. We had everything we needed and enjoyed our time either around the pool or in the games room. We spoke to Bill during our stay who was really lovely and willing to help us with anything we needed. The Windows hills site was great with a lovely communal pool area and a few slides. The site is very secure. I would not hesitate to book here again as it was everything we wanted and more.

You might like these similar properties

Your dates are Available!

Total

Includes taxes and fees
$423+
View details