Hi Kenneth,
I can set you up with some current Naples area listings (from our local MLS) that are along the lines of what you describe. I can also have new listings automatically come to you via email if you're interested in that. Here's one Naples property that's similar to what you're talking about:
http://matrix.swflamls.com/Matrix/Public/Portal.as...
If you go up a bit, say $300-325K, then you have a few more choices. Summer is a good time to buy - at least in Naples - because it's our slow season and there are quality houses that will end up sitting on the market until things pick up again in the fall. Sellers may be more flexible this time of year.
Regarding the HOA fees, yes $300-600 are pretty typical, but rather than proximity to the beach, they're primarily driven by amenities and the other things the HOA pays for (insurance, community pool, maintenance, etc.). The more the HOA does or provides, the more you pay. One possible exception is when you have a small association. They may not provide much, but the costs can be high because they are split among so few owners.
I really love Naples. It's laid back but has most of what larger metros have due to the high number of affluent residents. One of the safest cities in Florida, as well. You kind of get the best of both worlds.