We have rented four different houses from four different owners since 2002. Each rental went perfectly. In each case I rented directly with the owner, 3 European owners, one American.
We even had the owners call us. I guess they must be worried about renting as well, I imagine they want to avoid having the place trashed by a bunch of young houligans.
I guess we must sound pretty tame over the phone.
I talked to the management company on 3 of the 4 rentals. It helped me ease into my comfort zone.
Also, we chose homes with reasonable rates each time. Even if we had been burned, it would not have been the end of the world.
Now, one of my aunts rented a huge house in Florida on the gulf, probably either Navarre Beach or the Destin area a couple of years ago. Their entire extended family including 5 daughters and several of their granddaughters' families all were going. They paid $10 grand for one week. The place was a disgrace. They ended up complaining and got their money back. It did ruin their vacation. They rented through a management company.
Before kids we used to head down to the panhandle each Memorial Day weekend with friends and never rented the same place twice. We found the more we paid, the better the place. Some were immaculate, some were horrible. We stayed in one place that amazing. You just never know.