I second PSUforever's recommendation of Naples. Go to the Naples Pier at sunset. Consider chartering a boat for fishing for half a day. (Of all things, I remember the name of my best charter, Captain Bubby Hail -- some people just go to the same spot time after time. He would go to different spots based on the conditions) Was reasonable when I did that about 15 years ago -- I did it in the summer and we fished for grouper. Almost certainly you can do the same in Ft. Myers.
Many high end developments in Southwest Fla. which you can easily find on your own. So, I will focus more on the lower end to give you a broader range of recommendations. In Fort Myers, Cape Coral is lower end but probably OK. Golden Gate in Naples used to be on the wrong side of the tracks, but might be a reasonable deal now. (About 8 miles from the Gulf) Consider looking at homes around the La Playa golf course in North Naples. It used to be a blue collar golf course called Palm River, which was plowed under for the much higher end La Playa. Homes there might be comparatively reasonable. Also, consider the Imperial Development in North Naples by Imperial Golf Club. In the past, I would characterize these homes as being slightly upper middle class. This is all from my memory of about 15 years ago. If things have changed, I am sure others will correct me.
For some winters my father was a winter golf pro in Naples, and he bought acreage at a good time, which I helped him sell.
Might want to check out Bonita Springs which is in between Fort Myers and Naples on the southernmost end of Lee County. Again on the high end, there are a large number of choices. Not far from the airport, but I don't know much about Bonita.
Wish you good luck.