Welcome To Windsor Hills!

Windsor Hills Resort is the premier vacation rental resort in the heart of Florida’s world-class vacation destination! Located in Kissimmee, Florida, Windsor Hills Resort is just minutes from Walt Disney World® , Disney Springs, ESPN Sports Complex, Universal Studios, Sea World,  Gatorland, and more! 

This exclusive gated rental community offers privately owned rental properties that are uniquely geared toward enhancing your family’s vacation.   Unlike most generic “Airbnbs”, you will have direct access with the rental owner and their on-site management contact before and during your stay.  

Our beautifully landscaped, meticulously maintained resort community features a 24/7 staffed gatehouse, a fully staffed clubhouse, fitness center, gameroom, resort pool, sports courts, waterpark, and more!  Lit pathways, community sidewalks, playgrounds, picture-perfect photo-spots, nightly movies and weekend poolside entertainment make your Windsor Hills Resort vacation rental a true home away from home!

Unlike staying in a hotel, you can easily have groceries, DoorDash, InstaCart and Amazon packages delivered right to your rental property doorstep.  Ride share services like Uber and Lyft are readily and easily available, as well.

Windsor Hills Resort is a short 35 minute ride from Orlando International Airport (MCO), 1 hour from Sanford Airport (SFB) and approximately 1.5 hours from Tampa International Airport (TPA). 

There are over 100 restaurants within a 10 minute driving radius, as well as Margaritaville’s Sunset Walk and Island H2O.  Nearly every store you may need is also a quick drive away, including Target, Super Walmart, Publix, Costco, CVS, Starbucks, medical services including urgent cares, and more!

It doesn’t get any closer to the action — just look us up on GoogleMaps to see how CLOSE we are to everything! Windsor Hills Resort’s address is  2600 Old Lake Wilson Road, Kissimmee, Florida 34747.

Windsor Hills Resort Vs. other rental communities

5 Minutes To WDW

It doesn't get any closer to Walt Disney World® -- see for yourself on Google Maps!

No Resort Fees

No resort fees, no parking fees, no hidden fees. Transparent pricing direct with the rental owner.


Your Windsor Hills Resort rental includes access to all amenities including the pool and waterpark!

Guest Service

Your property manager is just a phone call or text message away when you rent in Windsor Hills Resort.