Entire home

Welcome to The Windsor Dream!

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 12260.1 sq m

Popular amenities

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

Explore the area

Map
Kissimmee, FL
  • Mystic Dunes Golf Club
    ‪7 min drive‬
  • ESPN Wide World of Sports Complex
    ‪12 min drive‬
  • Disney's Animal Kingdom® Theme Park
    ‪19 min drive‬
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪22 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.

*** 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! ***

Property manager

Bill and Donna
Premier Host

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Amenities

Pool
Hot tub
Kitchen
Washer
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 - 7 min drive - 5.2 km
  • Disney's Blizzard Beach Water Park - 11 min drive - 8.5 km
  • ESPN Wide World of Sports Complex - 12 min drive - 9.9 km
  • Disney's Hollywood Studios® - 12 min drive - 9.8 km
  • Disney's Animal Kingdom® Theme Park - 19 min drive - 13.9 km

Getting around

  • Kissimmee Station - 26 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 22 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Taco Bell - ‬4 min drive
  • ‪IHOP - ‬3 min drive
  • ‪Giordano's - ‬4 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 Island H2O Live! and Walt Disney World® Resort. Old Town and Disney's Hollywood Studios® 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. 157 out of 160 reviews
Rating 8 - Good. 2 out of 160 reviews
Rating 6 - Okay. 1 out of 160 reviews
Rating 4 - Poor. 0 out of 160 reviews
Rating 2 - Terrible. 0 out of 160 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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 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

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

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

David N.

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

Great Home!!

Had a great time with the family at this home. This house was perfect!!
Stayed 3 nights in Jun 2019

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

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

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

Christie L.

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

Great location

Close to Orlando and the house itself is very close to the resort. Also, south facing pool was great for sunshine and no rear neighbors was amazing! Very clean and hosts were great to work with.
Stayed 7 nights in Jan 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

Ken D.

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

Great place for our family vacation!

Bill and Donna were great host. The home was clean and stocked with all of our needs. The pool/spa area was perfect and we spent most of our time outside. Great location to restaurants, Disney properties, Universal, and Sea World. Thank you for making our vacation so wonderful! We would definitely stay again!
Stayed 7 nights in Jun 2021

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

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
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Linda T.

Very Nice Home Convenient to Disney

The home was as lovely as the description and pictures portray! The ride into Disney was very easy and the owners are great communicators. Definitely recommend.
Stayed 5 nights in Jan 2017

10/10 Excellent

Tiffannie C.

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

Excellent

We had a wonderful stay! The property was lovely and the communication with the owner was outstanding. We look forward to returning. Thank you!
Stayed 3 nights in Dec 2019

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

Mari-Elena B.

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

Great long weekend with friends!

We had the best time at Welcome to the Windsor Dream! From grilling, to concerts, to afternoons in the pool and hot tub, Bill made our stay perfect. And the location can't be beat. We will be back!
Stayed 4 nights in Oct 2021

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

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

Lauren J.

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

Wonderful House

The house was perfect for our group of 6 adults and 1 child. The pool and hot tub were our favorite after a long day at the parks! Location was great and the house was clean and well taken care of. The owners were very nice, responsive, and informative. We would definitely rent from them again!
Stayed 6 nights in Oct 2022

10/10 Excellent

Shanecia C.

Very nice

The house was very nice nd clean nd we real enjoyed our stay i would definitely book with them again the house was amazing just like the pictures.
Stayed 3 nights in Mar 2019

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

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