What About Whimsey?

Everything you need to know about Whimsey of Windsor Hills!

The definition of Whimsey is "Playfully quaint and fanciful" , a design theme you will find to be evident throughout.  Whimsey of Windsor Hills is a place for families to relax and enjoy one another's company, making memories to be cherished for a lifetime.  Privately owned by our family, we are honored to share it with yours!

 Welcome to our Whimsical Family!

✔️ LIST:

✔️ 6 Bedrooms, 4 Baths
✔️ $20,000 in 2020 updates! Delightfully Refreshing
✔️ Star Wars Game Room with Pool Table, Foosball and Black Light Air Hockey and Karaoke Machine
✔️ Sunny, Southwest Facing Pool and Spa, Fully Screened, Super Private Setting
✔️ Child Safety Pool Fence
✔️ 4 Sun Loungers
✔️ Backyard with Family Favorite Games
✔️ 4 Burner Gas Grill
✔️ Covered Lanai Furnished for Dining and Lounging
✔️ Great Room with Soaring 25ft Ceiling and 55” Smart HDTV
✔️ Open Concept
✔️ Well Stocked Luxury Kitchen, Newly Updated
✔️ Coffee Bar Including Espresso Machine
✔️ Main Floor Laundry
✔️ Smart HDTV’s and Fans in all Bedrooms
✔️ Hairdryers in All Bathrooms
✔️ Lots of Towels, Pool Towels and Linens
✔️ Tinkerbell Tea Party
✔️ Children's Toys and Family Games
✔️ 2 Pack & Play, 2 High Chairs, 4 Strollers, Baby Activity Seat, Bouncy Seat, Baby Swing, Bed Rail
✔️ Just around the corner from the Cutest Castle Themed Play Park Ever!
✔️ Short Walk to Resort Pool, Waterpark and Club House
✔️ Smoke Free and Pet Free (A must, as owner has allergies!)
✔️ Keyless Entry and Expedited Check-in with Preregistration 
✔️ FREE Access to Resort Amenities 
✔️ FREE Wi Fi


Main Floor

❤️ Poolside King Master with Spacious En Suite Bath
❤️ Elegant King with En Suite Bath
❤️ Whimsical Queen for the Young at Heart!
❤️ ½ Bath

2nd Floor

❤️ Large King with Pool View
❤️ Disney Cars Themed Bedroom with Race Car Beds
❤️ Frozen Themed Bedroom with Walk-Up Bunk Beds
❤️ Full Bath


Why Windsor Hills?

To begin with, you just can not top Windsor Hills as a community.  There may be other newer communities, but you simply can not beat Windsor Hills for it's charm and family friendly atmosphere.  We looked at every community within the shadow of Disney, and it just had to be Windsor Hills!  Besides being the CLOSEST VACATION HOME RESORT COMMUNITY TO DISNEY, the grounds are impeccably maintained, and the amenities are incredible.   All freely available to our guests, you gotta love it!

Regarding security, Windsor Hills is a seriously guard gated community.  All guard gated communities are not created equal! To enter Windsor Hills you MUST be registered with the guard gate.  Some communities are not able to deny access.   If the county is responsible for the streets in the community, no one may be denied access.   Windsor Hills Condo Association maintains their own streets, not the county.  Policies are strictly enforced, making our community very secure.  This is what we want for our family, and yours! 


Why Whimsey?

Where to begin?  Being privately owned, we are personally vested in providing a stellar vacation experience for every one of our guests.  We feel we can make a difference in the details.  Instead of walking into a cold impersonal hotel room, you enter a home lovingly furnished.  We want the families we host to find themselves in an environment that delights and surprises, conducive to the creation of cherished family memories.  

Our location within Windsor Hills is special.  We are tucked into a quiet corner on a larger than average lot.  We actually have a spacious back yard to play games in!  And it faces southwest, so we get lots of sun on our pool and spa.  Other pools may face south, but the closeness of the homes causes shadows to be cast a good part of the day.  We have sun all day, in a very private setting.  No need to frost the panels of our pool enclosure, creating a stuffy claustrophobic environment.  Whimsey of Windsor Hills is the perfect private oasis to relax and enjoy your family in!

Our unique 6 bedroom floor plan is rare in Windsor Hills.  We offer a soaring 25' ceiling in our open concept great room.  The entire home from top to bottom has been reimagined to create Whimsey of Windsor Hills!  We were going for "playfully quaint and fanciful. . .", the very definition of "Whimsey". Just what every Disney vacation should be about! 



Book your next family adventure at Whimsey of Windsor Hills for lifelong memories.
Or better yet. . .
Make Whimsey your family tradition for a lifetime of “Whimsical” memories!






In this current environment it is more important than ever to make thoughtful choices when we travel.

  The health and safety of ourselves and our families depends on it. 

Please rest assured that we are dedicated to providing a clean and safe environment for our guests.

  Whimsey of Windsor Hills undergoes a thorough professional cleaning and sanitizing between each group.

   Our guests can enjoy peace of mind knowing they are experiencing a high level of housekeeping and hygiene efforts. 




FREE access to resort amenities. Resort Zero Entry Lagoon Style Pool, Water Park and Water Slides, Splash Pad, Hot Tub, Fitness Room, 10,000 square foot Club House, Game Room, Movie Theater, Convenience Store, Tennis Courts, Basketball Court, Putting Green, Parks, Oversize Vehicle Parking Lot
Property Type House
House Rules
  • Children welcome 
  • Pets not allowed
  • Smoking not allowed
  • Limited accessibility
  • Minimum age of primary renter: 21
Setting & View
  • Resort 
  • Internet 
  • Telephone 
  • Air Conditioning 
  • Central Heating 
  • Linens Provided 
  • Towels Provided 
  • Washing Machine 
  • Clothes Dryer 
  • Private Living Room 
  • Fitness Room/Equipment 
  • Hair Dryer
  • Iron & Board
  • Basic Soaps
  • Paper Towels
  • Shampoo
  • Toilet Paper
  • Kitchen 
  • Refrigerator 
  • Stove 
  • Oven 
  • Microwave 
  • Dishwasher 
  • Dishes & Utensils 
  • Coffee Maker 
  • Toaster
  • Ice Maker
  • Blender
  • Kettle
  • Child's Highchair
Bathrooms 3 Bathrooms, 1 Half bath
  • King En Suite – Shower, Toilet, Tub 
  • King En Suite Bath – Combination Tub/Shower, Shower, Toilet, Tub 
  • Main Floor Bath – Toilet 
  • 2nd Floor Bath – Combination Tub/Shower, Shower, Toilet, Tub 
Towels and Hair Dryers in all Bath Rooms
Bedrooms 6 Bedrooms, sleeps 8-12
  • Disney Cars Bedroom – 2 Twin beds 
  • Main Floor King Master – 1 King bed 
  • Main Floor Queen – 1 Queen bed 
  • King Guest Room – 1 King bed 
  • Frozen Room – 1 Bunk bed 
  • Main Floor King Master – 1 King bed 
Smart HDTV's and Fans in all Bed Rooms
  • Television 
  • Satellite/Cable
  • DVD Player 
  • Video Library
  • Video Games 
  • Music Library
  • Games 
  • Books
  • Toys 
  • Game Room 
  • Pool Table 
  • Foosball
  • Outdoor Grill
  • Deck/Patio (uncovered) 
  • Lawn/Garden 
  • Tennis 
  • Walkable to Golf
  • Veranda 
  • Beach Essentials
  • Communal Pool 
  • Private Pool 
  • Hot Tub 
  • Indoor Pool
  • Heated Pool
  • Family
  • Health/Beauty Spa
  • Museums
  • Theme Parks
  • Water Parks
  • Zoo
  • Outlet Shopping
  • Shopping
Sports & Adventure
  • Basketball Court
  • Golf
  • Swimming
  • Deadbolt Lock
  • Emergency Exit Route
  • Fire Emergency Contact 
  • Fire Extinguisher 
  • First Aid Kit
  • Exterior Lighting
  • Police Emergency Contact 
  • Smoke Detector