I live about 50 minutes from Philadelphia, which in my opinion is the closest STR market I can think of.

Closest is in Knoxville, about 45-60 mins away and is not well attended.

Where your closest friends (the ones your trust) live now or nearTake that list and compare it to hot or trending markets around the country and see if there are some matches.

Or, you can do nothing although I do think your original cleaning company should reimburse you back the $300 for the crummy job they did.This is a bit like tenants who complain when a refrigerator goes on the fritz all those steaks, lobsters and shrimp just got spoiled to heck and they want reimbursement for those.   

Your closest examples would be USVI, Guam, and Northern Mariana Islands but for some reason not Puerto Rico.

Currently we are interested in Cayce (the portion closest to the Congaree River), Forest Acres, Lexington, and Irmo.

Possibly FL just since it’s closest to where I’m located (Caribbean).

The closest thing I could find is VRBO confirming they waive their fees if either party cancels and Booking.com confirming they only charge a fee for confirmed stays.  

It's the closest one to Naples. 

We just had a meetup earlier this month in Albany which I think would be the closest to you.