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Windsor Hills Retreat

Villa with 6 bedrooms, 4 bathrooms, private pool and golf nearby in Windsor Hills, Florida

From $1,896 per week

Contact Owner

Spacious luxury property situated at the top of the exclusive gated community of Windsor Hills in Kissimmee. Private south facing pool and spa. 2 miles from Disney and Universal is 15 mins drive away.


Windsor Hills Retreat is a fully air conditioned spacious 6 bedroom, 4 bathroom luxury property located at the top of the prestigious guard gated Windsor Hills community in Kissimmee, Florida.

The property sleeps 12 people and features the largest floor plan available within the community with a whirlpool spa pool that flows into the palm tree lined private south facing swimming pool.

The property spans approximately 3,000 square feet and has been furnished in a sophisticated yet modern style and the owners have included many of the various amenities that you would normally expect at a luxury hotel. The bed linen is at least 350TC white Egyptian cotton and the bath towels are luxuriously heavy and fluffy white Turkish cotton.

The property features a formal living and dining room to the front. A large family room and kitchen featuring stainless steel appliances, granite counters, breakfast bar and an informal dining area are located to the rear of the property with large glass slider doors out to the pool and spa. The washing machine and dryer are located in a separate laundry room on the ground level.

Free wired and wireless high speed internet is provided as well as a Microsoft xBox 360 and Nintendo Wii with a selection of games for both.

A large 55" LCD HD TV sits in the family room, 40" LCD HD TV is provided in the formal living room and large LCD TVs are also provided within every bedroom. Cable TV is provided throughout the house including digital video recording and premium channels such as HBO and ESPN. Blu-Ray and/or DVD players are provided in each bedroom and living area.

A Harley Davidson themed games room completes the ground floor level and features a full size 8ft slate base professional pool/billiards table and a Harley Davidson foosball table.

Upstairs there are five large bedrooms, including two private US king size (UK super king size) master bedroom suites, a large US queen size (UK king size) bedroom and two twin bedrooms. A further queen size sixth bedroom is located on the ground level overlooking the swimming pool and spa and has an adjoining bathroom.

Outside there is a large south facing brick paved pool deck with a covered lanai (patio) with cooling ceiling fans to provide shade when needed. Plenty of outside seating and sun beds are provided as well as various pool toys.

Golf and Theme Parks
Walt Disney World is located 2 miles from the property and Universal Studios/Seaworld are only a 15 minute drive away.

There are numerous golf courses located within a 15 minute drive of the property including Mystic Dunes which backs on to the property.

Windsor Hills Resort Facilities - Included for Free
In addition to the various amenities included within the property, as a guest at Windsor Hills Retreat you will be able to gain access to the private resort clubhouse.

The clubhouse has a very large free form swimming pool, heated spa pool, childrens water slide, sundry shop, cinema, video games arcade, gym, tennis courts, golf putting green and volleyball court.

Rental licence or registration number: State of Florida Resort Dwelling License no. #DWE5917028


52 verified reviews

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Value for money

49 out of 52 people recommend staying here


Family from Roseville, USA Mar 2021

Wonderful property and owner. The owner's attention to detail and communication was exceptional. We knew exactly what to expect and had no trouble getting in touch with any question we had. When we arrived, the house was extremely clean and had everything that the owner said it would have. The kitchen has plenty of dishes and the appliances are excellent quality. There were also many extras like a full-size crib for our toddler, a high-quality stroller, toys, books, games, and movies. It really showed that this a home the owner also uses for vacation. We have stayed multiple times in Windsor Hills resort, and this house and owner were definitely our favorite. Highly recommend.


Family from State College, USA Dec 2020

Property is just as described in the listing. The first word that comes to mind at describing this home is spacious. We enjoyed the separation of rooms. The two master bedrooms with attached bathrooms were awesome. The shear size of the rooms was perfect for our family. The pool was a hot spot even on cool nights. The hot tub did take roughly 40 minutes to heat up but it was worth the wait. The kitchen appliances were upgraded and in great working condition. The added bonus of baby supplies such as cribs, highchair, toys and other equipment was perfect for our families needs. The game room was also fun to use. The valet trash was exceptional. Who gets trash pick up from your front porch everyday (except Wednesdays)? Tv's in every room was great, it was difficult to determine which remote controlled what but it was manageable when we did use it. Overall the perfect house for large families and families with kids. We will definitely consider this home for our next trip to Orland and you should too.


Family from Springfield, Canada Feb 2020

My Husband and I stayed with our 2 children, as well 2 adult family members. (4 adults, 2 kids).

It was perfect for our family, - everyone had their own privacy (bedroom, and bathroom). It wasn’t tight by any means with this many people. The Xbox and Wii in each of the children’s bedrooms were a bonus. The games room was excellent to have on our days that we didn’t have any parks to visit. After visiting the parks, the spa was a nice treat to relax in.

We highly recommend this place to anyone with children. The gated entry made everyone feel safe, and the location is quiet and yet relatively close to many attractions.

The owner was extremely accommodating and a pleasure to communicate with.


Large Group from Charlottetown , Canada Feb 2020

Natasha’s house was absolutely beautiful, the layout was great, a separate living room and a family room were perfect, the master bedrooms were awesome!...I will stay here again!...thanks Natasha!


Family from West Grove, USA Dec 2019

Our stay was as close to perfect as you can get. We spent New Years week here and had a great time. The house was perfect for us. It has lots of space for everyone. After a long, crazy day at Disneyworld, we were happy to have such a nice retreat to unwind. I definitely recommend renting with Natasha. She was wonderful and always available for my questions and concerns.


Family from Llanfechain, United Kingdom Dec 2018

Just back from another enjoyable stay at Windsor Hills Retreat. The villa was the same as last time, beautifully presented and with the lovely heated (payable extra) pool just makes the perfect base for exploring Orlando & further a field.
We love the christmas decorations up too as feels like home from home then.
Dealing with Natasha is always a pleasure.
We are just looking at times we can go back and enjoy it yet again.
Highly recommend!

9 other reviews

Sharon B. Jun 2019

Home was exactly as listed. All necessities were first class and fully furnished. Natasha was quick to answer emails to questions. Our family enjoyed our stay even though it rained a lot of the time we were there.

David E. May 2019

Stayed in this lovely villa at the end of May for 10 days. Modern, clean and well positioned. Kitchen well equipped with everything you need. Modern, comfortable living areas with good choice of TV channels. My 8 year old boys loved the games room with pool table! Pool area is great with sun all day long, water temperature was nice as weather was so good when we were there. Lots of information inside the house regarding the house itself and all the parks etc. Lots of games and books too which was nice. Bedrooms all very nice with comfortable beds, again my boys loved the game consoles in a few of the bedrooms. Owner was great to deal with, very prompt and gave us lots of information about the area prior to our visit. Windsor Hills is a lovely resort, the communal pool is fantastic for the children with a large pool and water park which is wonderful. 5 mins to Disney, Walmart just down the road along with lots of restaurants etc. Overall wouldn’t hesitate to recommend this lovely villa to anyone! Thank you for a very enjoyable stay!

Lisa M. Apr 2019

Our stay was wonderful ! My husband and I and our 2 kids ages 5&2 stayed with another couple and their son age2. The house was perfect !! The house was spotless when we arrived. Beds and sheets are so comfortable. The crib was so handy! And there are a few Toys which was nice ! The kitchen is so well equipped I was very impressed, from a Mickey appetizer bowl to a kitchen aid mixer it has anything you need! The back yard is nice and private and gets sun all day long. We added the pool heat which made it so comfortable for our end of April stay. Very close to Disney even with traffic one evening to Disney springs didn’t take long at all. I would definitely book this house again! Natasha was great to deal with she responded to any questions very quickly.

Mary Kay S. Apr 2019

Super comfortable! Plenty of room and lots of amenities. We had a fabulous time!

Siobhan J. Mar 2019

This home was nicely decorated and clean. Our family enjoyed the pool. Natasha was pleasant and responded back to all of our questions promptly. We would definitely stay at this property again.

Kimberly E. Mar 2019

Thanks so much for the wonderful home. Beautiful decor, great location (less than 5 minutes to Disney, ~15 min to Universal). Well stocked. Plenty of space. Responsive and friendly owners. We couldn’t figure out the spa/hot tub and the owner helped us through it with patience. Would love to visit again next time we’re in Orlando!

Daniel R. Jan 2019

We had a great stay at this property! Owners were quick to respond and the house is awesome!

Thashieka C. Nov 2018

My Family and I loved it. Very family oriented and kid friendly. We had ages of 2months to 60 years and everyone was well accommodated. We will definitely book again!

Shannon L. Oct 2018

We absolutely loved this home and will use it for future vacations. Super clean and had everything you needed. Owner is very in tune to her customers making sure everything is ready and perfect

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Distances to locations

Nearest beach 50km Nearest bar 1km Nearest restaurant 3km Nearest supermarket 5km Orlando International Airport 35km Walt Disney World 5km Universal Studios and Island of Adventures Parks 25km Seaworld and Discovery Cove 18km Cocoa Beach 110km

Local activities

Fishing 15km Golf 500m Horse riding 15km Sports center 500m Swimming 500m Tennis 500m Water skiing 15km Wind surfing 15km

Sights and attractions

Museum 40km Night club 18km Shopping 5km Theme park 5km Zoo 5km

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Prices and availability

Updated 4 May 2021

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Changeover days and minimum stays

  • 14 May - 24 September 2021: the minimum stay is 4 nights.
  • 25 September - 5 December 2021: the minimum stay is 5 nights.
  • 6 December - 17 December 2021: the minimum stay is 4 nights.
  • 18 December 2021 - 7 January 2022: the minimum stay is 6 nights.
  • 8 January - 24 September 2022: the minimum stay is 4 nights.
  • 25 September - 5 December 2022: the minimum stay is 5 nights.
  • 6 December - 16 December 2022: the minimum stay is 4 nights.
  • 17 December 2022 - 6 January 2023: the minimum stay is 6 nights.
  • 7 January - 24 September 2023: the minimum stay is 4 nights.
  • 25 September - 5 December 2023: the minimum stay is 5 nights.
  • 6 December - 17 December 2023: the minimum stay is 4 nights.
  • 18 December 2023 - 7 January 2024: the minimum stay is 6 nights.
  • 8 January - 14 May 2024: the minimum stay is 4 nights.

Compulsory extras

  • Pool Heating - is included in our prices

    $0.00 per bookingpaid with booking

  • COMPULSORY CLEANING FEE: If your stay is for less than 7 nights a $150 fee will be charged.

    $150.00 per booking if the booking is for less than 7 nights, paid with booking

Optional extras

  • BBQ Grill rental (cost/week)

    $65.00 per week, paid with booking

  • Early check in - 1pm (usual time is 4pm) CONFIRM WITH OWNER BEFORE SELECTING THIS OPTION

    $100.00 per booking, paid with booking

  • Late check out - 1pm (usual time is 10am) CONFIRM WITH OWNER BEFORE SELECTING THIS OPTION

    $100.00 per booking, paid with booking

  • Additional whole house clean

    $150.00 per booking, paid with booking



6 bedrooms, Sleeps 12:

  • 1 king size bed and en suite
  • 1 king size bed and en suite
  • 1 king size bed and en suite
  • 1 king size bed
  • 2 single beds
  • 2 single beds

There is also 2 cots


4 bathrooms including 3 en suites

Swimming pool

Private pool with electric heating


DVD/Blu-ray player, WiFi / WiFi, Radio, Telephone, TV Languages in English, Spanish, Satellite / cable


Living area seats 12, Dining area seats 12, Air conditioning throughout property, Central heating, Clothes drier, Hair dryer, Iron / board, Towels / linen, Washing machine, High chair, Car hire recommended


Cooker, Crockery, Cutlery, Dishwasher, Fridge, Freezer, Glassware, Kettle, Microwave, Oven, Pots / pans, Toaster


Outside lighting, Parking, Tennis court


Gym, Jacuzzi, Snooker / pool table

Leisure resort

Children's pool, Gym, Tennis

Suitable for

Children, Infants, Single gender groups

Extra information

In addition to the various amenities included within the property, as a guest at Windsor Hills Retreat you will be able to gain access to the private resort clubhouse. The clubhouse has a very large free form swimming pool, childrens water slide, sundry shop, cinema, video games arcade, gym, tennis courts, golf putting green and volleyball court.


Average rating from 52 reviews

Private Owner From London, United Kingdom Member since May 2010

Past bookings: 168 bookings

Response rate: 80%

Response time: within 17 minutes

Last logged in: 12 hours ago

Number of properties: 1