A family-friendly stay in Kissimmee awaits you at this villa. You'll be 3 km (1.8 mi) from Mystic Dunes Golf Club and 4.6 km (2.8 mi) from Island H2O Live!. .Villa features a private pool, a washing machine and free WiFi. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. 5 bathrooms, a patio and a living room are also available. .Enjoy the gym and Hot tub. Additionally, you'll find laundry facilities, a games room and a garden.
Disney's Animal Kingdom® Theme Park - 8 min drive - 4.5 km
Disney Springs™ - 12 min drive - 13.8 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
Osaka Bay Buffet - 3 min drive
Sickies Garage Burgers & Brews - 3 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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! ***
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
Deadbolt lock
General
Bicycles
Garden
Property located in a resort
Unit size: 2,800 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 23
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Once your reservation has been confirmed we will forward to you a copy of our Guest Registration Form for your electronic signature.
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.
Property Registration Number DWE5914079
Property is also known as
Welcome To The Windsor Dream
Welcome to The Windsor Dream! Villa
Welcome to The Windsor Dream! Kissimmee
Welcome to The Windsor Dream! Villa Kissimmee
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Frequently asked questions
Are there any beaches close to Welcome to The Windsor Dream!?
The closest beach to Welcome to The Windsor Dream! is Getaway Glen (8.2 km).
Does Welcome to The Windsor Dream! have a pool?
Take your pick from a heated pool, a pool and a communal pool.
What luxury perks are available at Welcome to The Windsor Dream!?
This property features a heated pool, as well as a private pool and a living room.
What makes Welcome to The Windsor Dream! a romantic place to stay?
1 hot tub, private pools, and private patios all help set the scene for a sizzling getaway at Welcome to The Windsor Dream!.
Is Welcome to The Windsor Dream! family-friendly?
You bet! With amenities such as an arcade and laundry facilities, as well as highchairs and travel cots, it's no surprise that Welcome to The Windsor Dream! is a winner with our family travellers.
Is there a private hot tub at Welcome to The Windsor Dream!?
Yep, there is a hot tub.
Is there a free airport shuttle available at Welcome to The Windsor Dream!?
No, Welcome to The Windsor Dream! does not offer an airport shuttle service.
What time are check-in & check-out at Welcome to The Windsor Dream!?
Check-in begins at 4:00 PM. Check-out time is 10:00 AM.
Are pets allowed at Welcome to The Windsor Dream!?
No, pets are not allowed.
Welcome to The Windsor Dream! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 166 out of 170 reviews
10 - Excellent
166
Rating 8 - Good. 3 out of 170 reviews
8 - Good
3
Rating 6 - Okay. 1 out of 170 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 170 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 170 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
DanSara D.
26 Feb 2026
Liked: Cleanliness
The host walked the fine line of being available and giving us the information we needed without being overbearing. The house was just what we expected. Loads of fun for the kids and a perfect space for our family to meet up and spend time together. The heated pool was perfect, even on the cool (below 70 degree) days. There were strollers, high chairs, and pack and plays for the babies. It was a very quick drive to and from Disney World and shopping and restaurants were also close by.
DanSara D.
Stayed 7 nights in Jan 2026
10/10 Excellent
Derek T., Medina, MN
4 Jan 2026
Liked: Cleanliness
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!
Derek T.
Stayed 5 nights in Dec 2025
8/10 Good
sue s.
29 Dec 2025
sue s.
Stayed 4 nights in Sep 2025
10/10 Excellent
Craig B.
28 Dec 2025
Liked: Cleanliness
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.
Craig B.
Stayed 5 nights in Dec 2025
10/10 Excellent
Lisa S., Antioch, IL
18 Dec 2025
Liked: Cleanliness
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!
Lisa S.
Stayed 7 nights in Nov 2025
10/10 Excellent
Kristen B.
11 Dec 2025
Liked: Cleanliness
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.
Kristen B.
Stayed 6 nights in Nov 2025
10/10 Excellent
Jason T.
10 Aug 2025
Liked: Cleanliness
Wonderful home, nice location.
Jason T.
Stayed 7 nights in Aug 2025
10/10 Excellent
Mark R.
7 Jul 2025
Liked: Cleanliness
Great vacation home
Beautiful home, close to basically everything, pool was great, kids loved the game room, would visit again
Mark R.
Stayed 7 nights in Jun 2025
10/10 Excellent
Corey W.
21 Jun 2025
Liked: Cleanliness
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!
Corey W.
Stayed 5 nights in Jun 2025
10/10 Excellent
Chris A.
23 Apr 2025
Liked: Cleanliness
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.
Chris A.
Stayed 4 nights in Apr 2025
10/10 Excellent
Vitaliyd12 D.
22 Feb 2025
Liked: Cleanliness
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!
Vitaliyd12 D.
Stayed 6 nights in Feb 2025
10/10 Excellent
Amanda R.
10 Jan 2025
Liked: Cleanliness
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!
Amanda R.
Stayed 7 nights in Dec 2024
10/10 Excellent
Sarah w.
8 Sept 2024
Liked: Cleanliness
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.
Sarah w.
Stayed 8 nights in Aug 2024
10/10 Excellent
Lauren B.
15 Aug 2024
Liked: Cleanliness
Great, quiet location
Lauren B.
Stayed 4 nights in Aug 2024
10/10 Excellent
Julian N.
14 Aug 2024
Liked: Cleanliness
Great property
Julian N.
Stayed 7 nights in Jul 2024
10/10 Excellent
Ryan G.
28 Mar 2024
Liked: Cleanliness
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.
Ryan G.
Stayed 4 nights in Mar 2024
10/10 Excellent
Stacee K.
8 Mar 2024
Liked: Cleanliness
Spring Break Getaway
We enjoyed a nice week at Windsor Hills. Everything as described and pictured. Pool area was the shining star of the house. Our kids ages 11-2 loved the house pool, but also the “big pool” that the resort offers. Both pools were so warm—-we loved it!
Bill was so easy to communicate with. Very responsive, and took time to send thoughtful ideas about local attractions and food suggestions we might want to check out.
It was clearly communicated that there was no extra supplies, just a starter supply, but In stays at other venues, we have had a “seasoning/spice cupboard” as we do quite a bit of cooking/grilling. Or at least salt/pepper…I’m sure this is for sanitation/health reasons, but we missed having these on hand. This is more of a heads up to other guest who may be wondering, not a complaint. Also no “cleaners” on hand to spray on counters/etc. This was okay as we used dish soap, but just a side note.
Honestly, it was a perfect vacation, and we could not have been more pleased with our stay.
Thank you for all of your thoughtful planning, we especially appreciated the virtual “guestbook” that we referenced many times during our stay. We had zero issues with codes, checking in, getting our wristbands for resort, everything was seamless.
Thank you!
Stacee K.
Stayed 6 nights in Mar 2024
10/10 Excellent
Dan D.
16 Jan 2024
Liked: Cleanliness
Nice place, excellent location
Communication with the property owners was great. If anything, it was maybe a bit too much! Lots of emails beforehand letting us know the process for getting to the house and through the security gate. Everything went smoothly though once we arrived. Location is excellent for Disney and ESPN fields. Walmart is extremely close for supplies. Kitchen very well stocked with utensils, pots and pans, and tupperware. Garbage bags were the only thing pretty lacking - we only got 1 for a 4 night stay with 7 people. Plenty of towels, blankets, pillows. Beds all very comfortable. House itself is nicely decorated for a rental. Game room was pretty dark and items in it were all well worn, but to be expected for a game room. Pool and hot tub are really nice. Temperature was pretty cool while we were there, but the pool was nice and warm, and the hot tub can actually be cranked up to real hot tub temps! We didn’t use it much because of the cool weather, but we did check out the community pool / area, and it seemed very nice as well. Overall, we really enjoyed our stay and would return.
Dan D.
Stayed 4 nights in Jan 2024
10/10 Excellent
Shaniqua J.
1 Jan 2024
Liked: Cleanliness
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!!!
Shaniqua J.
Stayed 5 nights in Dec 2023
10/10 Excellent
Michael J.
7 Dec 2023
Liked: Cleanliness
Excellent
Great property to stay in. Awesome family friendly neighborhood. Definitely coming back.
Thank you Bill and Donna.
Respectfully,
Michael
Michael J.
Stayed 7 nights in Nov 2023
10/10 Excellent
Andy A., San Diego, USA
8 Oct 2023
Liked: Cleanliness
Amazing stay at Windsor Dream!
We loved everything about staying at this home. Also, working with Bill and Donna was a dream. My husband, daughter and I travel frequently and use home rentals often. Bill and Donna are extremely welcoming hosts. They are in contact from day one with information. They have an app just for their home and is a great resource. It didn’t matter what kind of questions we had (and we had a lot-we were a party of 12) Bill and Donna would respond quickly. We stayed here with family and enjoyed a week of fun and visiting the theme parks nearby. This house is the perfect location for doing all of that.
The house is exactly as described. We loved having 5 bedrooms and 5 bathrooms. So much space for everyone. No one felt crowded and it was nice to have our own bedrooms for each family. We also felt the living space (open kitchen, living room, dining room) are well laid out that provide lots of space to relax, watch tv and hang out together. I remember when we booked the home I thought, wow, 2 washer and dryers feels like a lot. Little did I know that having 12 family members (3 are children), would generate a lot of laundry. It was a very nice touch. Also we loved their kitchen! Perfect for cooking full meals and snacks.
We really utilized the amenities on our days off from the parks. Having our own pool at the house was everyone’s favorite part of the home. We look forward to staying at the Windsor Dream again!
Andy A.
Stayed 6 nights in Sep 2023
10/10 Excellent
Robert G.
7 Sept 2023
Liked: Cleanliness
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.
Robert G.
Stayed 6 nights in Aug 2023
10/10 Excellent
JAY P.
17 Jul 2023
Liked: Cleanliness
Orlando 2023
Great Place to stay!!!!! Owner was always accommodating!!! SUPER NICE PEOPLE!!!!!!
JAY P.
Stayed 8 nights in Jul 2023
10/10 Excellent
Nancy S.
28 Jun 2023
Liked: Cleanliness
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
Nancy S.
Stayed 6 nights in Jun 2023
10/10 Excellent
Mom c.
14 Jun 2023
Liked: Cleanliness
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!