This is not going to be helpful really but, I used to have the good fortune of knowing the manager of a hotel on Vanderbilt called the Vanderbilt Inn and spent several very happy weekends there. I think it was an older hotel it had a retro feel, but it was such a magical place and the beach front there was second none. They tore it down to build condos last year.
The point I'm trying to get to is it was the last hotel on the beach. Now it is all condo and beach house rentals. But, if you find something on Vanderbilt I think there is a 99.9% chance that it will be very nice. I have not seen anything that looked run down around there.
Also if you are in the Naples area you have to visit Tru Lucks in Naples on or around Fifth Avenue. Best service, best stone crab, best oysters I have EVER had. Love the place.
I think I'm rambling now, so I will stop.