I have rented out some of my pied-à-terres to strangers even via free online listings. Never had a bad experience yet. All but one time, I was able to return the security deposits in full. [The one time I wasn't able to return the security deposit it was because I lost contact with the person after the refund check was returned to me as undeliverable by the postal service.]
I almost always rented out to couples or visiting business persons.