We just booked there for the first time this past weekend. This will be our first stay off-site (after nearly 20 trips). Our family needs more space now, and we're going the week between Christmas and New Years (don't laugh - it's the only time that worked for everyone), so we couldn't afford our usual 2 rooms at Pop with the Christmas pricing. Since everyone speaks so highly of Windsor Hills, we decided to give it a try. We ended up booking through the site run by the HOA:
But we also looked at WH properties on VRBO & AirBnB. We ended up going through the HOA site because it was the lowest price. Honestly, our biggest hangup about the whole thing was the cancellation policy. We're just used to hotels, where you cancel right up to the day or two before the trip. We almost booked through VRBO, because the cancellation policy there was better (but still not good), but ultimately booked through the HOA site for the lower price and bought travel insurance to cover just the rental cost.
We booked through VRBO. Their search functionality was more robust, and I couldn't find anything cheaper for what we wanted on the HOA site, at least not without what seemed like excessive effort. Plus a 30-day full cancellation policy (or better) was a high priority for me. We had a reservation for 2020 that we had to cancel, and it was seamless.
Great point about searching - the HOA site is clunky. Also, not everything that is available appears on the HOA site. I saw a WH owner post on another forum that the HOA site only includes owners who are in good standing with the HOA (which is a good thing, but still, it limits availability). Another thing she mentioned is that some property management companies only allow listings on one site (or only on certain sites), so for those properties even owners in good standing don't appear on the HOA site.