Entire home

Welcome to The Windsor Dream!

Family-friendly stay near Mystic Dunes Golf Club

Choose dates to view prices

Photo gallery for Welcome to The Windsor Dream!

A large swimming pool surrounded by palm trees and a gazebo.
A modern kitchen with stainless steel appliances, a microwave, and a built-in oven.
A stone archway with a pathway leading through it, surrounded by greenery and a statue.
A covered outdoor area with a pool, dining table set for four, and two ceiling fans.
A living room with a leather sectional sofa, a glass coffee table, and a view of a golf course through large windows.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 122800 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪3 min drive‬
  • Place, Bonanza Golf & Gifts
    ‪4 min drive‬
  • Place, Island H2O Live!
    ‪6 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪33 min drive‬

Room options

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About the neighborhood

Kissimmee

Windsor Hills stay.Your stay at this Windsor Hills villa places you within 3 miles (5 km) of Mystic Dunes Golf Club and Island H2O Live!. Walt Disney World® Resort and ESPN Wide World of Sports Complex are also within 6 miles (10 km).

What's nearby

  • Mystic Dunes Golf Club - 3 min drive - 1.1 miles
  • Bonanza Golf & Gifts - 4 min drive - 2.1 miles
  • Mighty Jungle Golf - 4 min drive - 2.3 miles
  • Island H2O Live! - 6 min drive - 2.6 miles
  • Orange Lake Golf - 7 min drive - 4.5 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
  • ‪El Cafetal Bakery & Restaurant - ‬3 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪IHOP - ‬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.

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! ***

Similar properties

Property amenities

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transportation

  • Car recommended
  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • 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

  • Smoking not allowed

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)
  • Deadbolt lock
  • Fire extinguisher

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

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
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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite 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 each 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
orp5b413d9x

Frequently asked questions

How close is Welcome to The Windsor Dream! to the airport?

This villa is 12.5 mi (31-min drive) away from the Kissimmee, FL (ISM-Kissimmee Gateway) airport, the closest popular airport to the property.

Does Welcome to The Windsor Dream! have an airport shuttle?

Airport shuttle services are not available at this villa.

How close is Welcome to The Windsor Dream! to the beach?

This villa is 8.5 mi (20-min drive) from Beachcomber Beach and 9.2 mi (22-min drive) from Hideaway Bay. Don't forget your sunscreen!

Does Welcome to The Windsor Dream! offer free breakfast?

This villa does not offer free breakfast.

Is there a casino at Welcome to The Windsor Dream!?

No, there is no casino at this villa.

What time is check-in at Welcome to The Windsor Dream!?

Check-in begins at 4:00 PM.

Is there free parking at Welcome to The Windsor Dream!?

Free parking is not available at this villa.

Does Welcome to The Windsor Dream! have a pool?

Yes, there's a private pool.

Does Welcome to The Windsor Dream! have a spa?

There are no spa services available at this villa.

How close is Welcome to The Windsor Dream! to downtown Kissimmee?

This villa is 2.3 mi away from Four Corners.

Welcome to The Windsor Dream! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 169 out of 173 reviews
Rating 8 - Good. 3 out of 173 reviews
Rating 6 - Okay. 1 out of 173 reviews
Rating 4 - Poor. 0 out of 173 reviews
Rating 2 - Terrible. 0 out of 173 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

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

10/10 Excellent

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
Verified review

10/10 Excellent

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

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
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.
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 5 nights in Dec 2025
Verified review

10/10 Excellent

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

Great place for our family vacation!

Bill and Donna were great host. The home was clean and stocked with all of our needs. The pool/spa area was perfect and we spent most of our time outside. Great location to restaurants, Disney properties, Universal, and Sea World. Thank you for making our vacation so wonderful! We would definitely stay again!
Stayed 7 nights in Jun 2021
Archival

10/10 Excellent

Very Nice Home Convenient to Disney

The home was as lovely as the description and pictures portray! The ride into Disney was very easy and the owners are great communicators. Definitely recommend.
Stayed 5 nights in Jan 2017
Verified review

10/10 Excellent

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

Excellent

We had a wonderful stay! The property was lovely and the communication with the owner was outstanding. We look forward to returning. Thank you!
Stayed 3 nights in Dec 2019
Verified review

10/10 Excellent

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

Great long weekend with friends!

We had the best time at Welcome to the Windsor Dream! From grilling, to concerts, to afternoons in the pool and hot tub, Bill made our stay perfect. And the location can't be beat. We will be back!
Stayed 4 nights in Oct 2021
Verified review

10/10 Excellent

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

Orlando 2023

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

10/10 Excellent

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
Verified review

10/10 Excellent

Very nice

The house was very nice nd clean nd we real enjoyed our stay i would definitely book with them again the house was amazing just like the pictures.
Stayed 3 nights in Mar 2019
Verified review

10/10 Excellent

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

Close to everything

We had such a wonderful family vacation here. We were close to all the parks, dining, shopping. There was enough space for all of us to relax after a full day of being in the sun. If we ever visit again would love to stay here again. Thank you so much.
Stayed 7 nights in Aug 2022
Verified review

10/10 Excellent

Awesome

Great place to stay for all ages! Beautiful and large home . Snack shack, community pool, game room, park, etc all very close and fun! Owners were VERY nice and easy to work with! No complaints!
Stayed 7 nights in Dec 2018
Verified review

10/10 Excellent

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

Wonderful House

The house was perfect for our group of 6 adults and 1 child. The pool and hot tub were our favorite after a long day at the parks! Location was great and the house was clean and well taken care of. The owners were very nice, responsive, and informative. We would definitely rent from them again!
Stayed 6 nights in Oct 2022
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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