Whether it’s your first time booking a vacation rental, or you’ve visited Windsor Hills Resort in the past, we know you may have some questions. We want you to have all the information you need to have the best time possible at Windsor Hills!

Have a question that isn’t here?  Hop on over to the Windsor Hills Resort Facebook group, where dozens of helpful owners, as well as guests past and present, are ready to assist!

Are there shuttles or busses to the Disney Parks from Windsor Hills Resort?

There are not.  You are approximately 5 minutes from Walt Disney World property by car.  One of the biggest benefits of staying “off site” is the freedom of easily coming-and-going with your own car.  You’ll find yourself getting to and from the local attractions much faster than if you were relying on resort transportation! Beware of “off site” resorts that do offer shuttles as they come with a lot of fine print, and generally only run once or twice per day!   The owner you rent from will be happy to help you with rental car recommendations and the latest deals.

How much does it cost to use the resort amenities like the waterpark, clubhouse and fitness center?

All resort amenities are free and included with your vacation rental!  This includes Sir Windsor AquaVenture Water Park, the heated Resort Pool, all Clubhouse amenities, Fitness Center, Playgrounds, Sports Park, Picnic Area, etc.

Is there a calendar of entertainment offerings?

Yes there is, click here to see our  Activities Calendar!  Most months feature a similar schedule, with movies and music/band/DJ entertainment subject to change.  Printed calendar sheets are available at the Clubhouse when you arrive.

How do I book a property?

Visit the Book Now page to search our real-time inventory of rentals.  Then click on the rental(s) you are interested in to see more information, photo galleries, to contact the rental’s owner directly, or to instantly book online! No dealing with call centers, unresponsive owners, or third parties.   Only owners using secure, direct, hotel-caliber software are permitted to list on the Windsor Hills Resort website.  Rental agreements, policies, payment methods, deposits, and payment schedules vary by rental.

What are the benefits of booking a vacation rental?

Short-term rentals offer several benefits over traditional hotel stays, including:  more space, privacy, and the ability to cook your own meals. Short-term rentals can also be more cost-effective for longer stays, larger groups, or travelers seeking a more relaxing stay. Your rental is truly your Home Away from Home. 

What if I need assistance during my stay?

Most rentals will have a property manager or on-site staff available to assist with any issues or questions that may arise during your stay. Contact information for the property owner, manager or staff should be provided in the rental information.  The staffed clubhouse is available to assist with resort questions and questions about the local area, but are generally unable to assist with questions about specific rentals.

What is the cancellation policy?

Cancellation policies will vary depending on the specific property. Be sure to review the cancellation policy on the Rental Agreement before booking to ensure you understand the terms and conditions.  If you have concerns about  possible unforeseen circumstances interrupting your travel plans, we strongly recommend purchasing Travel Insurance.  There are many coverage options available, and most owners provide a link to purchase at the time of booking. 

I see other Windsor Hills Resort rentals on Airbnb, and some of those prices seem too good to be true. Why is that?

Assuming the listing is legitimate, some owners prefer to be completely hands-off with rental operations. Therefore, they may choose to outsource it to a full-service, big box rental agency.  The expression “you get what you pay for” is never more true in these situations.  Listings such as these are not bookable via our website. The listings you find on this website are verified owners who are actively engaged in the day-to-day oversight of their rental property(s).

What are the hours of the resort pool, waterpark and clubhouse?

The main Resort Pool and Clubhouse are open 8:00 AM – 10:00 PM.  The Water Park is open 10:00 AM – 8:00 PM.  Hours are subject to change due to weather or unplanned operational changes.

Can I receive Amazon deliveries, InstaCart, and use rideshare services?

Yes, yes and yes!  In fact, one of the best parts of a vacation rental vs a hotel room is having deliveries made RIGHT to your front door.  All major shipping carriers (except USPS) deliver to Windsor Hills Resort rentals.  Uber and Lyft are also widely used, but be sure to text the driver the main gate entrance address in addition to your rental address!  The Clubhouse cannot accept deliveries or store luggage.  Deliveries must be arranged AFTER you arrive.  It is strongly encouraged to work directly with a big-name provider like Amazon, Walmart or Instacart and not independent shoppers or concierge services.  See more info about grocery delivery here.

Are pets permitted?

Pets are not permitted in any condo rentals. In the townhomes, there is a weight limit of 25 pounds if the owner allows pets in their rental.  With the rental villas/houses, the policy is up to the individual owner.

How many vehicles can we bring into Windsor Hills? What about over-sized vehicles, like an RV?

This varies by rental, and is best answered by the individual owner you are renting from.  As a rule of thumb, there is generally a hard limit of 2-3 cars per rental, though in some circumstances approval for additional vehicles may be possible.  Over-sized vehicles such as trailers must be pre-approved and arranged through the owner you are renting from.  There is a special parking lot for over-sized vehicles.  Untagged vehicles will not be permitted entry.

How do we gain access to the resort pool and waterpark?

Once you arrive, head on down to the Clubhouse Welcome Center where our friendly staff will issue you enough wristbands for your group.  They’re free, and are your pass to enjoy all the amazing Windsor Hills amenities.

Is the vacation rental I book the one I am going to actually stay in?

YES! Unlike booking through Airbnb or the big-box Orlando rental agencies where there is a high likelihood of being moved to another rental at the last-minute, when you book direct you are entering into an agreement with ONE particular rental property.  You will have a direct communication channel with the owner at all times.

Is there a map of Windsor Hills Resort?

The most useful map is going to be Google Maps — particularly satellite or ‘earth’ view.  The Clubhouse and Resort Pool/ Waterpark are near the Teascone and Comrow intersection.  The main gate Reception Booth and resort entrance is nearest to Teascone and Old Lake Wilson Blvd.  (Please note the alternate entrance on Livingston is a service entrance only).

Do we need a parking pass or confirmation slip for when we check-in at Windsor Hills Resort?

The owner you book through will confirm that they have registered your group with the Gatehouse, generally a week before you arrive.  Anyone driving a vehicle will also need to present a valid drivers license upon arrival.  As Windsor Hills Resort is a gated community, non-guests are not permitted access so we encourage you to confirm your guest list details with the owner you are renting from. The Gatehouse is manned by Resort Staff 24 hours a day, and after your initial registration you will be printed  Resort Passes for easy exit/entry.

Is Windsor Island, Windsor Palms or Windsor Westside related to Windsor Hills Resort?

No.  These rental communities share no relationship other than the name “Windsor” which was popularized due to the success of Windsor Hills Resort.  These other locations are significantly further from the theme parks.