Top Windsor Hills Vacation Rental Reviews

Verified Vacation Rental Reviews by Real Guests

Amenities: Gated entrance and a multi-million dollar clubhouse. Onsite convenience store and video rental. Barbecue area and RV parking. There is a shuttle service is provided by a third party company that will take you to Disney. There is a per person fee which will be paid locally. Activities: Lagoon-styled double Olympic beach-entry heated swimming pool with water slide, a water play area,... read more
Amenities: Gated entrance and a multi-million dollar clubhouse. Onsite convenience store and video rental. Barbecue area and RV parking. There is a shuttle service is provided by a third party company that will take you to Disney. There is a per person fee which will be paid locally. Activities: Lagoon-styled double Olympic beach-entry heated swimming pool with water slide, a water play area, Jacuzzi, a 48-seat movie theater, fitness center, pool tables, ping pong and foosball tables and a huge children's play area. Outdoor activities include basketball, tennis, baseball, and sand volleyball. Distances: Windsor Hills is located 1.5 miles from Disney World and 15 minutes from Universal and Sea World. Located on the 192 and close to local amenities, such as banks, restaurants and supermarkets. There are 2 golf courses as near as a 2 minute drive. Tampa to the west and Cocoa beach to the East are approximately a one hour drive. Orlando International is only 25 minutes away.
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Today's Top 11 Windsor Hills Vacation Rental Reviews

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  • Windsor Hills 6-Bed Pool

    Kissimmee: Windsor Hills: House
    6 BDR • 4 BA • Sleeps 15 • #231083
    1 star 2 star 3 star 4 star 5 star
    Kevin says ‘Spacious and clean’
    We enjoyed our stay at this house. Comfortable beds and furniture and the house is clean. Great location on a quiet street with plenty of sun with a west facing pool.
    Stayed with family - Recommended to friends and family
  • Sunny South Facing Private

    Kissimmee: Windsor Hills: House
    6 BDR • 4 BA • Sleeps 14 • #241446
    1 star 2 star 3 star 4 star 5 star
    Deborah says ‘Loved our Vacation’
    We thoroughly enjoyed our stay at the Windsor Hills home. It was beautiful, so spacious, and so clean. The community pool and water slides were terrific, as was the private pool and hot tub at the home. We took full advantage of them each day. The location to all of the Disney parks was perfect too! We would highly recommend this home to any family traveling to the Orlando area. Hope we can do it again. Thank you for sharing this home with us.
    Stayed with family - Recommended to friends and family
  • Orlando Sunshine Getaway

    Kissimmee: Windsor Hills: Villa in a gated community
    5 BDR • 5 BA • Sleeps 11 • #243536
    1 star 2 star 3 star 4 star 5 star
    Andrew says ‘Wonderful Property’
    We had a fantastic time at this property - everything was exactly as described. Comfortable, spacious, fun, and a great place to relax between Disney parks.

    The only problem we had was getting Ubers and Lyfts to come to the property. The "map" on their apps continuously sent drivers to the wrong entrance with no one manning the gate. There are signs at those gates directing drivers where to go, however, a majority of the drivers we encountered did not speak English, so they could not follow the signs. Highly recommend if you are going to use Uber and Lyft to have someone in your party who can speak Spanish to direct them.

    While it was a minor speed bump, the amount of money you save by not staying on a Disney property was worth the inconvenience.
    Stayed with self - Recommended to friends and family
  • Luxury 6br Windsor Hills

    Kissimmee: Windsor Hills: Villa
    6 BDR • 4 BA • Sleeps 14 • #243123
    1 star 2 star 3 star 4 star 5 star
    Mark says ‘Great Location’
    Fantastic villa, lovely pool, great location close to all theme and water parks.
    Could not have wished for anything else.
    Stayed with family - Recommended to friends and family
  • Townhome in Gated

    Kissimmee: Windsor Hills: Townhouse in a gated community
    3 BDR • 3 BA • Sleeps 6 • #244988
    1 star 2 star 3 star 4 star 5 star
    Timothy says ‘Enjoyed Our Time’
    The patio pool worked great for our two little ones, and the community pool was a short walk up the street. The house was well equipped with everything we needed. Really liked the added touch of chips and salsa on arrival. Location was convenient to Disney and restaurants and Walmart. Beds were comfortable. Plenty of towels. Everything was very clean.
    Stayed with family - Recommended to friends and family
  • Only 2 Miles to Disney

    Kissimmee: Windsor Hills: Villa
    6 BDR • 4 BA • Sleeps 12 • #243120
    1 star 2 star 3 star 4 star 5 star
    Anne says ‘Beautiful House, SO Convenient for Summit!’
    We rented this house for Summit 2019 in the ESPN Centre, and it was the best choice we could have made. We were going in the other direction from the traffic the entire time! The parks were close and convenient, and the house was just beautiful. Check-in was a breeze even though five families stayed there, and the owners and rental company communicated clearly and helpfully. I’m never staying on property at Disney for Summit again!
    Stayed with friends - Recommended to friends and family
  • Windsor Hills Luxury Villa

    Kissimmee: Windsor Hills: Villa in a gated community
    6 BDR • 4 BA • Sleeps 16 • #207232
    1 star 2 star 3 star 4 star 5 star
    Isabelle says ‘Fantastic place’
    I really enjoyed the place. The owner is great and flexible. The location is perfect for Walt Disney and the complex with the pool is amazing for kids. I would rent this property anytime
    Stayed with friends - Recommended to friends and family
  • Luxury 5br Windsor Hills

    Kissimmee: Windsor Hills: House
    5 BDR • 5 BA • Sleeps 12 • #246624
    1 star 2 star 3 star 4 star 5 star
    Chris says ‘Good resort, poor house ’
    This home was in a convenient location. It fit a large number of guests, and it did have some nice, updated decor. But we had a lot of issues with this house.
    We weren’t at the house much, basically for breakfast and sleep, so all the following issues were not reported. Wasn’t much they could do about fixing ALL the broken things while we were there and it didn’t seem worth it to complain since they do not offer refunds and we weren’t even there much. But it definitely didn’t seem worth the price or feel as safe cleanliness wise, considering Covid, with all the trash found upon arrival.
    I would recommend the resort due to location, close to parks. But I would not recommend this particular property. In need of lots of maintenance.

    The issues we found were as follows:
    -Foot of Star Wars beds were broken.
    -Closet in Star Wars room was broken.
    -Lamp in Star Wars room was broken.
    -missing battery in led lights in Star Wars room
    -patio door to the pool was extremely loose and made an awful sound when opening and closing.
    -cigarette butts by the pool.
    -juice cap trash by pool
    -broken table and lounge furniture by pool
    -trash in garage under bistro table and pool table
    -light switch in the garage was broken
    -shower door in master suit was loose
    -shower door in second downstairs bedroom was loose
    -guest double stroller had a broken wheel on the back right side.
    -kitchen cabinets and drawers were broken and falling off hinges.
    -closet door in Moana room was broken.
    -overall cleanliness was not great.
    -exterior of home needs maintenance. Overgrown landscape, weeds growing up through patio, algae around pool, dirty windows, benches, sidewalk.
    -stove burners took forever to heat up
    -garbage disposal did not work properly

    Whole house just needs lots of updates and maintenance.

    Stayed with friends - Would not recommend to friends and family
  • Luxury Windsor Hills 6br

    Kissimmee: Windsor Hills: Villa
    6 BDR • 4 BA • Sleeps 14 • #243122
    1 star 2 star 3 star 4 star 5 star
    Michelle says ‘Disney family vacation’
    Very easy to rent from owner direct, had no issues there. Although the house was a nice size and fit all of our guests comfortably, it was a bit rundown. There were things that needed to be fixed up and it was not very clean. We also encountered some issues with multiple roaches throughout the house not to mention there were half smooshed ones on the walls. We were not even able to go into the game room due to multiple roaches spotted in there and it smelled not so good.
    Stayed with family - Would not recommend to friends and family
  • 5br/5ba Luxury Pool Villa

    Kissimmee: Windsor Hills: Villa
    5 BDR • 5 BA • Sleeps 12 • #243125
    1 star 2 star 3 star 4 star 5 star
    Florinda says ‘Very bad customer service from Nova vacation and Homero Cardenas property managment’
    I rented a house with a pool so we could enjoy the Florida weather and oh surprise that my family and I got when we arrived. The pool was completely dirty, the water was green as if it had weeks of not being clean. I immediately reported it to property management and they replied to me two days after. To make the story short, I called them every day because they kept telling me that they were gonna go but never did until the day we left. Oh and I still do not understand what they did to it because the pool still looked dirty.
    I cannot say I enjoy my stay with them because the service was horrible, I paid a cleaning fee of 500.00 prior my arrival to get to a clean house and I got there and found a filthy pool. My kids were not able to enjoy the stay either because they wanted to enjoy the pool.
    Bad, bad service!!
    Stayed with family - Would not recommend to friends and family
  • Lake View New Luxury Pool

    Kissimmee: Windsor Hills: Villa in a gated community
    5 BDR • 5 BA • Sleeps 12 • #243427
    1 star 2 star 3 star 4 star 5 star
    Amira says ‘False Photos’
    These photos are very old and very edited and the house does not match this at all. It was very outdated and not clean! We had nothing but issues the entire time. I would not recommend this to anyone.
    Stayed with family - Would not recommend to friends and family
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