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Welcome to The Windsor Dream!

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A heated pool
TV, video games, video library
Fridge, microwave, oven, stovetop
Dining
Property grounds

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 12260 sq m

Popular amenities

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

Explore the area

View map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪20 min walk‬
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪6 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪32 min drive‬

Room options

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  • Spa pool
  • Kitchen
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4.7 out of 5, Exceptional, 3 reviews
Renovated Jan 2024 5BR luxury villa in Grand Windsor Hills, 5-Star gated resort

About the area

Kissimmee

With a stay at this villa in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. .This family-friendly villa is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Disney's Hollywood Studios®.
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What's nearby

  • Mystic Dunes Golf Club - 20 min walk - 1.7 km
  • Bonanza Golf & Gifts - 3 min drive - 3.1 km
  • Walt Disney World® Resort - 6 min drive - 5.1 km
  • Disney's Animal Kingdom® Theme Park - 7 min drive - 4.8 km
  • Disney Springs™ - 11 min drive - 13.7 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
  • ‪Sickies Garage Burgers & Brews - ‬3 min drive
  • ‪Drafts Sports Bar & Grill - ‬14 min walk

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! ***
Make yourself comfortable in this air-conditioned villa, which features a private pool. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Enjoy recreational amenities such as a hot tub and a fitness center. Additional features at this villa include an arcade/game room and barbecue grills.
Guests will find features like internet access.

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

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in 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

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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

We should mention

A car is recommended for transportation 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

Welcome to The Windsor Dream! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 163 out of 166 reviews
Rating 8 - Good. 2 out of 166 reviews
Rating 6 - Okay. 1 out of 166 reviews
Rating 4 - Poor. 0 out of 166 reviews
Rating 2 - Terrible. 0 out of 166 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Lisa S., Antioch, IL

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!
Stayed 7 nights in Nov 2025

10/10 Excellent

Kristen B.

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.
Stayed 6 nights in Nov 2025

10/10 Excellent

Jason T.

Liked: Cleanliness
Wonderful home, nice location.
Stayed 7 nights in Aug 2025

10/10 Excellent

Mark R.

Liked: Cleanliness

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

Corey W.

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!
Stayed 5 nights in Jun 2025

10/10 Excellent

Chris A.

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.
Stayed 4 nights in Apr 2025

10/10 Excellent

Vitaliyd12 D.

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!
Stayed 6 nights in Feb 2025

10/10 Excellent

Amanda R.

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!
Stayed 7 nights in Dec 2024

10/10 Excellent

Sarah w.

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.
Stayed 8 nights in Aug 2024

10/10 Excellent

Lauren B.

Liked: Cleanliness

Great, quiet location

Stayed 4 nights in Aug 2024

10/10 Excellent

Julian N.

Liked: Cleanliness

Great property

Stayed 7 nights in Jul 2024

10/10 Excellent

Ryan G.

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.
Stayed 4 nights in Mar 2024

10/10 Excellent

Stacee K.

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!
Stayed 6 nights in Mar 2024

10/10 Excellent

Dan D.

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.
Stayed 4 nights in Jan 2024

10/10 Excellent

Shaniqua J.

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!!!
Stayed 5 nights in Dec 2023

10/10 Excellent

Michael J.

Liked: Cleanliness

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

Andy A., San Diego, USA

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!
Stayed 6 nights in Sep 2023

10/10 Excellent

Robert G.

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.
Stayed 6 nights in Aug 2023

10/10 Excellent

JAY P.

Liked: Cleanliness

Orlando 2023

Great Place to stay!!!!! Owner was always accommodating!!! SUPER NICE PEOPLE!!!!!!
Stayed 8 nights in Jul 2023

10/10 Excellent

Nancy S.

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
Stayed 6 nights in Jun 2023

10/10 Excellent

Mom c.

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!
Stayed 6 nights in Jun 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness

Perfect Disney/Orlando stay!

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

10/10 Excellent

Kyle R.

Liked: Cleanliness

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

Jennifer M.

Liked: Cleanliness

Perfect Getaway

We had a great experience renting Bill and Donna’s house to go to Disney World with family and friends. It is close to the parks which is key because the traffic is heavy in Orlando. The house is just as described it is beautiful and clean and has everything you need and want. It is also in a gated community which we wanted. The pool is south facing which is perfect to get sun all day and heated so it is warm and the hot tub is perfect after a long day at the parks. There is also a club house with a large pool and playground/water slides snack bar/store that is walking distance from house. The kitchen is well equipped with everything you need and even has a gas grill outside to barbecue. The bedrooms are decorated beautifully and some have Disney/universal themes and the beds are very comfortable. We enjoyed using the game room at night playing pool and video games. Bill and Donna are very nice and attentive and although we didn’t need them for anything during our stay they checked in frequently to make sure we were doing okay and also gave us recommendations of places to shop, eat and activities they thought we may enjoy. We will definitely be back and stay here again! Jen M
Stayed 5 nights in Feb 2023

10/10 Excellent

Lori P.

Liked: Cleanliness

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