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.

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).

Welcome to The Windsor Dream! Reviews, Deals & Photos 2026

10/10 Excellent

Mark R.

7 Jul 2025

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

Chris A.

23 Apr 2025

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.

21 Jun 2025

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

Robert G.

7 Sept 2023

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

Michael J.

7 Dec 2023

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

Sarah w.

8 Sept 2024

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

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Guy B.

29 Jan 2024

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.

1 Jan 2024

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

10/10 Excellent

Ryan G.

28 Mar 2024

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

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Anh L.

8 Feb 2025

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

Donna H.

4 Mar 2025

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

Amanda R.

10 Jan 2025

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

Dan D.

16 Jan 2024

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

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.

Stayed 4 nights in Jan 2024

10/10 Excellent

Stacee K.

8 Mar 2024

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

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!

Stayed 6 nights in Mar 2024

10/10 Excellent

Andy A.

8 Oct 2023

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

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!

Stayed 6 nights in Sep 2023

10/10 Excellent

Jason T.

10 Aug 2025

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

Wonderful home, nice location.

Stayed 7 nights in Aug 2025

10/10 Excellent

Jennifer A.

30 Oct 2022

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

David N.

1 Jul 2019

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

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kym S.

8 Jun 2025

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

Ashley E.

25 Jan 2022

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

Vitaliyd12 D.

22 Feb 2025

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.

14 Jun 2023

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.

2 Mar 2023

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.

28 Feb 2022

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.

4 Feb 2022

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

Welcome to The Windsor Dream!

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