Entire home

Welcome to The Windsor Dream!

Family-friendly villa with a hot tub, near Mystic Dunes Golf Club

Photo gallery for Welcome to The Windsor Dream!

A heated pool - Welcome to The Windsor Dream! (Kissimmee)
TV, video games, video library - Welcome to The Windsor Dream! (Kissimmee)
Fridge, microwave, oven, stovetop - Welcome to The Windsor Dream! (Kissimmee)
Dining - Welcome to The Windsor Dream! (Kissimmee)
Property grounds - Welcome to The Windsor Dream! (Kissimmee)
Located in Windsor Hills, The Windsor Dream offers a luxury villa experience with a private south-facing pool and hot tub. As one of the closest homes to the amazing Windsor Hills Water Park and Clubhouse, enjoy access to amenities like a zero-entry community pool, basketball court, tennis courts, volleyball court, ping pong tables and putting green.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 122800 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

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! ***

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transport

  • Car recommended

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • TV with cable/satellite channels
  • Video games
  • Video library

Outdoor areas

  • Barbecue grill
  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Golf
  • Gym
  • Heated pool
  • Kayak
  • Tennis
  • Golfing nearby

Safety features

  • 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

Similar properties

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

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Property Registration Number DWE5914079
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

We should mention

A car is recommended for transport to and from this property

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
orp5b413d9x

About the area

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. Visit our Kissimmee travel guide
View more Villas in Orlando
Map
Kissimmee, FL

What's nearby

  • Orlando showing golf
    Mystic Dunes Golf Club
    20 min walk - 1.1 miles
  • www.alamy.com
    Walt Disney World® Resort
    6 min drive - 3.0 miles
  • www.alamy.com
    Disney's Animal Kingdom® Theme Park
    8 min drive - 2.8 miles
  • Disney Springs® showing a river or creek, a bridge and a sunset
    Disney Springs™
    12 min drive - 8.6 miles
  • Bonanza Golf & Gifts
    3 min drive - 1.7 miles

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

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).

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Welcome to The Windsor Dream! Reviews

Reviews

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.
More informationOpens in a new window
Rating 10 - Excellent. 165 out of 169 reviews
Rating 8 - Good. 3 out of 169 reviews
Rating 6 - Okay. 1 out of 169 reviews
Rating 4 - Poor. 0 out of 169 reviews
Rating 2 - Terrible. 0 out of 169 reviews

10

Cleanliness

10

Location

Reviews

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

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

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

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

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
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

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
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

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

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

Dan D.

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.

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.

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.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home, nice location.
Stayed 7 nights in Aug 2025

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
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

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

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

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