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
  • Outdoor space
  • Barbecue grill
  • Air conditioning

Explore the area

View in a map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪20 min walk‬
  • Place, Disney's Animal Kingdom® Theme Park
    ‪7 min drive‬
  • Place, Disney's Hollywood Studios®
    ‪9 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪34 min drive‬

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! ***

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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

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

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. Old Town and Flamingo Crossings Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Travelling with kids? Make time for Disney's Blizzard Beach Water Park, 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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
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

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

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
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

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

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

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

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

Danielle R.

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

Close to everything

We had such a wonderful family vacation here. We were close to all the parks, dining, shopping. There was enough space for all of us to relax after a full day of being in the sun. If we ever visit again would love to stay here again. Thank you so much.
Stayed 7 nights in Aug 2022

10/10 Excellent

Kyle R.

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

Excellent stay!

The house and community were as described. We had no issues with check in or check out. We would stay here again.
Stayed 6 nights in Feb 2023

10/10 Excellent

Michael R.

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

Great vacation property

We stayed on the area for a family wedding and wanted to take the kids the theme parks. The family enjoyed the pool and had a great time. Thanks!
Stayed 4 nights in Jan 2022

10/10 Excellent

Michael J.

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

Excellent

Great property to stay in. Awesome family friendly neighborhood. Definitely coming back. Thank you Bill and Donna. Respectfully, Michael
Stayed 7 nights in Nov 2023

10/10 Excellent

Robert G.

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

Great place and communication

Bill and Donna were great hosts and the place was awesome for our stay. They communicated everything we needed and more before, during, and after our stay. The house was beautiful, spacious, and the heated pool and hot tub was where we spent most of our time with sun all day. We will definitely be back.
Stayed 6 nights in Aug 2023

10/10 Excellent

Lori P.

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

A Great Two Weeks

Enough space for everyone in our group. Kids really enjoyed the themed bedrooms. Pool out back was used frequently and was very impressed with the amount of kitchen wares. Great location too - close to quite a few attractions in the area.
Stayed 13 nights in Jan 2023

10/10 Excellent

Alex G.

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

ESPN TOURNAMENT

Great location, property and owners. Everything g could not have gone smoother and the owners are extremely considerate and offer assistance with things in the neighboorhood! Very appreciative.
Stayed 3 nights in Nov 2022

10/10 Excellent

Sarah w.

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

We loved our stay here

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.
Stayed 8 nights in Aug 2024

10/10 Excellent

Casey C.

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

Family reunion in Kissimmee

We had a great experience at this property. It was the perfect home for our family reunion and plenty of space for our family - 8 adults and 1 toddler. The pool and jacuzzi were definitely highlights! Bill was very responsive and even offered suggestions on things to do and restaurants for our group. We felt very safe in the Windsor Hills resort and would certainly stay at this home again!
Stayed 9 nights in Aug 2021
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Guy B.

A bit of paradise!

My husband and I spent six nights at Windsor Dream, together with our 3 grandsons and daughter. It truly was a dream! The home was extremely well kept and the boys couldn’t get enough of the heated pool! The kitchen had everything you need if cooking is your preference and it really felt like home! Owners Bill and Donna were wonderful hosts and saw to our every need. We would highly recommend this rental!!!

10/10 Excellent

Shaniqua J.

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

Beautiful

Our stay was exactly what we were looking for! Bill and Donna were awesome from start to finish with the entire process. This was my family first time using a VRBO and I don’t think I would ever chose anything different in the future. The property and home was beautiful/clean, which made for an easy/relaxing Christmas vacation. I have already planned to rent two of their units for next year! If you are looking for great owners, beautiful property/home and an at ease worry free vacation….BINGO!!!
Stayed 5 nights in Dec 2023
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.

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

Ryan G.

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

So nice

Our family had a great time relaxing in the pool and hot tub. We loved the location. Very close to many restaurants and stores. We also went to Disney which was about 20 minute drive in traffic. It’s close distance wise, a little under 8 miles. Bill and Donna are in constant communication and really make you feel welcome in their beautiful home. Our younger boys loved the themed bedrooms and arcade room, and our teenage daughter loved the king bed in her room up stairs. Our family would love to stay at one of their properties for future trips to Orlando.
Stayed 4 nights in Mar 2024

10/10 Excellent

Verified traveller

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

Perfect Disney/Orlando stay!

This spacious, clean, and comfortable home was perfect for our extended family trip. Everyone had their own space. The private pool and spa were perfect after a day of crowds at the parks. The arcade room was a great hang out area for the kids. The club house and community water park was within walking distance. We appreciated the security of the gated entrance. The homeowners were incredibly communicative and so kind. We will definitely return!
Stayed 6 nights in May 2023

10/10 Excellent

Denise W.

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

Family Spring Break 2022

Our stay was absolutely amazing. The house was spotless and had everything that we could possibly have needed for our stay. The location to all the area attractions cannot be beat. You don’t want to spend needless time in the car getting to the attractions and this location was perfect. The resort had plenty to offer to keep our grandkids entertained. There was a small water park with slides that we all enjoyed and even a sand volleyball court that we enjoyed. The hosts, Bill and Donna, are amazing. Every contact with them was answered super fast and we could not have been happier that we chose the Windsor Dream for our family trip.
Stayed 6 nights in Mar 2022

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