I am one of those “strangers” that rents properties to visitors to The Villages. I am honest, responsible, and trustworthy. I ONLY rent through professional short and long term rental sites (like Vacation Rental By Owner and VillagesHomes4rent) but how would you know to trust me? Well, to start with, I have a track record, dozens of 5 star reviews from previous renters. Those reviews frequently extoll the virtues of the house and say something like “exactly as advertised”. This puts my guests at ease.

That said, I have friends who rent on Craigslist, and they are honorable, but I have also seen MY OWN HOUSE advertised on Craigslist(!), clearly a scam. So bottom line, check references. If you have doubts, talk to the owner. Make sure you know where your money is going, using a trusted intermediary if you can’t personally verify who you are dealing with.

Also use the property tax records to see who lives at the house you send the check too. If the house is not in the villages I would be a little more concerned at this time of the year.
You could look up the neighbors and send then a letter asking if they know of any problems. Get their name and address in the property records.

Thank you for all the suggestions and the PMs with additional suggestions and offers to help. I feel like I have done all the research I can reasonably do from 1000 miles away. I will check in with this thread in a few weeks and let everyone know if I made the correct decision.

It is safer to go through a real estate company to rent a home.

We used VH4R as a renter also. Great experience. Had peace of mind knowing the rental was legit as well as having someone we could contact locally if there were any issues (we did initially have a technical issue with the washer). Also when going with the owner direct, find out who does the cleaning? A professional company or the owner (who may not have the same standards).