Top-rated for its fully equipped kitchen, perfect for every meal.
Private garden
A rare find — relax in the peaceful, private garden space.
Centrally-located
You're never far from where you need to be with this convenient location.
5 bedrooms5 bathroomsSleeps 12
Popular amenities
Private pool
Hot tub on site
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Explore the area
Kissimmee, FL
Mystic Dunes Golf Club
Place, Mystic Dunes Golf Club
3 min drive
Bonanza Golf & Gifts
Place, Bonanza Golf & Gifts
4 min drive
Island H2O Live!
Place, Island H2O Live!
6 min drive
Orlando, FL (MCO-Orlando Intl.)
Airport, Orlando, FL (MCO-Orlando Intl.)
33 min drive
Rooms & beds
5 bedrooms (sleeps 12)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Bedroom 4
2 Single Beds
Bedroom 5
2 Single Beds
5 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Bathtub or shower · Toilet
Bathroom 3
Bathtub or shower · Toilet
Bathroom 4
Toilet · Shower only
Bathroom 5
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Garden
About this property
Welcome to The Windsor Dream!
Welcome to The Windsor Dream! We recently upgraded our game room to a professional arcade room. We have game rooms in some of our other homes. In this home it is a professional arcade with games you might find at Dave & Busters or Chuck-E-Cheese. We have an NBA basketball shooting game, Skee-Ball like you may have played at a seaside boardwalk arcade, and two Super Bike motorcycle racing games. You can play individually or go head-to-head in two player mode. We have an immersive Transformers game where two players sit inside the gaming cabinet to defeat the Decepticons together. We have a multi-cade system that has all of the classic arcade games from the 1980s on one machine, such as Pac-Man, Ms Pac-Man, Galaga, Donkey Kong, Frogger, Space Invaders, and more. Finally, we have an 8 foot long professional air hockey table. The best part? All of these games are set to "free play" for our guests - no quarters needed! Our arcade room has been completely finished and insulated, and the garage doors removed, so it is a true "room". It also has its own dedicated air conditioning system, making it quite cool - even in the warmer months.
In addition to looking at our Five Star reviews for The Windsor Dream, we invite all families considering our home to look at our reviews for our properties right next door at VRBO listing #840075, #93534, and #2548198. We are blessed to have received over 550 Five Star reviews across our homes, more than any other owner in Windsor Hills.
Discover Windsor Hills at The Windsor Dream. Bill and Donna's luxury villa at Windsor Hills, featuring a true south-facing private pool and hot-tub, with no rear neighbors. We are one of the closest homes to the amazing Windsor Hills Water Park and Clubhouse, about a 2 minute stroll away.
We own FIVE HOMES in Windsor Hills – Four of them are side-by-side: The Windsor Dream, The Windsor Magic, The Windsor Fantasy, and The Windsor Wonder, plus another home around the corner – The Windsor Treasure - so if you are traveling with friends or extended family please just let us know.
* Private South-Facing Pool, with No Rear Neighbors. Corner lot for even more privacy. * South-Facing Pools get the most sun all day. * Only 2.5 miles away from Disney. The closest resort that is not an actual Disney hotel. * One of the closest homes to the amazing Windsor Hills water park - just a 2 minute stroll away. * NO FEES for our guests to utilize the water park. * Enhanced COVID-19 cleaning procedures in place. * Contactless check-in via a personalized code for our electronic lock.
There are NO FEES for our guests to utilize the Water Park or Community Pool. We will provide the names of your family members to the Windsor Hills staff so there will be no cost for you.
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! ***
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Once your reservation has been confirmed we will forward to you a copy of our Guest Registration Form for your electronic signature.
Important information
You need to know
Property Registration Number DWE5914079
Property # 2064414vb
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.
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
About the area
Kissimmee
Windsor Hills, a neighbourhood in Kissimmee, is home to this villa. Old Town and Flamingo Crossings Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Travelling with kids? Make time for Disney's Blizzard Beach Water Park, or head to an event or a match at ESPN Wide World of Sports Complex. Spend some time exploring the area's activities, including golfing.
Kissimmee, FL (ISM-Kissimmee Gateway) - 31 min drive
Restaurants
Wawa - 5 min drive
McDonald's - 3 min drive
Chick-fil-A - 5 min drive
Starbucks - 3 min drive
7-Eleven - 4 min drive
Frequently asked questions
Does Welcome to The Windsor Dream! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Welcome to The Windsor Dream!?
As of 20 Aug 2026, prices found for a 1-night stay for 2 adults at Welcome to The Windsor Dream! on 31 Jan 2027 start from £1,618, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Welcome to The Windsor Dream! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Welcome to The Windsor Dream!?
On-site parking is available at the 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).
About the host
Hosted by Bill and Donna
Donna and I have been married for 33 years, and we have been blessed with 5 children, so we have many years left to enjoy the magic of Disney!
We fell in love with Windsor Hills since we are only 2.5 miles away from Disney, and very close to Universal Studios too. We also take time to travel to either coast to swim in the ocean as a day trip (just 1-2 hours away). We just love our location.
Why they chose this property
We rented many homes in Windsor Hills before purchasing our home. Our home backs up to the green conservation area, where no new homes can be built. This means when we are relaxing in our private pool, there are no other families behind us looking into our pool area. If you look at photos of other homes, you will see how close together the homes are - all back-to-back. In addition, since our home is on the end of our "row", the neighbors to the side are also a greater distance away. In our opinion our home is the most private in all of Windsor Hills.
What makes this property unique
Spend a moment viewing the Windsor Hills development on an aerial map. Most of the homes face north, east, or west – limiting the amount of sun the pool area will receive. When you view the aerial map, you'll see many of those pool areas covered in shade - even during the middle of the day. With our south-facing pool, the sun is always on our pool area.
Premier Host
They consistently provide great experiences for their guests