Windsor Hills Resort
Minutes From The Magic!
Book Direct With Owner Pricing
Just Minutes From Walt Disney World!


BOok direct & save.
Your Walt Disney World® And Central Florida Vacation Starts Here! Instantly Book Your Rental With Direct Owner Pricing.

Over 130 Windsor Hills Vacation Rentals Ready to Book DIRECT!

Windsor Hills Resort is situated just minutes away from Walt Disney World®  in Kissimmee, Florida, and is the closest vacation rental resort to the theme parks! Considered by seasoned Disney vacationers as the Best Kept Secret to Doing Disney, Windsor Hills Resort boasts OVER ONE HUNDRED rentals including multi-bedroom condos, townhomes and houses.  The best part?  Many of these spacious, modern Windsor Hills accommodations can cost substantially less than a tiny resort hotel room!

In addition to world class resort amenities and a 24/7 manned gatehouse, you’ll find modern, updated properties with the perfect amount of space to accommodate your family or group.  From in-home gamerooms, to fully themed Disney bedrooms, to spacious condos with balconies overlooking the waterpark — there is something for everyone just minutes from the magic at Windsor Hills Resort!


Windsor Hills Resort is the closest rental resort community to Walt Disney World®, and is only 35 minutes from Orlando Intl Airport.

EASY Check-in

No stopping at a busy rental office for keys on the other side of Orlando when you book direct. Go straight to your rental, enter the keycode, and begin your vacation!


Parking is free at Windsor Hills Resort. And there are no daily resort fees. Gatehouse is manned by Resort Staff 24 hours a day, 365 days a year.


Zero-entry heated lagoon pool, Sir Windsor AquaVenture Water Park, playgrounds, sports courts, staffed clubhouse, games room, movie theater, gym, entertainment and more! All included with your stay.

Disney World® Rental Houses, Condos, and Townhomes For Every Budget at Windsor Hills Resort.

This isn't just an Airbnb -- it's a Windsor Hills Resort vacation rental!

From multi-bedroom homes with private pools to comfortable high-end condos overlooking the resort pool and clubhouse, there is something for every taste and budget in Windsor Hills Resort!  Here you’ll find themed bedrooms, in-home game rooms and movie theaters, private laundry facilities, fully outfitted kitchens and more.  Each rental includes full access to all Windsor Hills Resort amenities including clubhouse, resort pools and waterpark.  Each accommodation is individually owned and managed, and as such, layouts, theming, decor, amenities and rental rates will vary by rental. 

There are three primary types of properties to choose from: condos, townhouses, and houses.  Occupancy varies by rental, with most houses capping out around 13 people.  

a resort hotel room is 1 bedroom, 1 bathroom, 350 sq ft ... and costs a fortune.

After a long day at the parks, the thought of waiting on multiple long bus lines, standing shoulder to sweaty shoulder on a resort bus, making several stops, and eventually cramming your family into a tiny resort hotel room isn’t exactly our idea of magical.  

Instead, zip on back to your multi-bedroom, multi-bathroom Windsor Hills Resort rental property just a couple minutes away!  Your own kitchen, your own bedrooms, your own space.  Vacation will have never felt so good!


Offering 3 bedrooms, with one on first floor, and two upstairs, Townhomes are a versatile choice for any group. They each feature an exclusive splash pool enclosed within a private lanai. Townhomes are just across the street from the Clubhouse and Resort Pool.

More Info


Available in 2- and 3-bedroom floor plans in the buildings closest to the Clubhouse and Resort Pool. All rooms are on one floor, and each has a private balcony or patio. Two large elevators service each building.

More Info

Not Sure?

Take a look through our real-time inventory of Windsor Hills Vacation Rentals -- we're sure you will find something you love. We have rentals of all types, sizes, and price points. No matter the rental type, it will include free access to all amenities including the Waterpark and Clubhouse!



Available in 4-, 5-, and 6-bedroom floor plans, our Houses / Villas offer a wide variety of choices to suit your group. All feature a private lanai with large pool, dedicated driveway parking, and ample living space. Many include themed rooms and in-house gamerooms!

More Info
BOOK direct, 

SAVE UP to 40% BY BOOKING DIRECT with an owner.

Skip Airbnb and Vrbo — here’s why.

Booking a vacation rental through the big name sites means paying some big booking fees.  

Windsor Hills Resort owners have come to together to launch a direct booking portal to help you save money while planning your family’s dream vacation!  By cutting out the “middle man” you can expect, on average, to save $474 by booking direct. Plus, you’ll be working directly with the owner of the rental — not someone in a callcenter who has never even stepped foot in the property!

Vacation rentals beginning at

$99.00 /per night

Windsor Hills resort:
LOCATION, location, location!


Main Entrance Gate:
2600 N Old Lake Wilson Blvd
Kissimmee, Florida 34747

please use this address for gps/nav. 

Tag your social media photos