We've wintered in the Naples area for the past two years and will do it again next year. Many, many beautiful Gulf beaches, lots of restaurants of all sorts from $ to $$$$. The 5th Ave area is great for walking, browsing, dining, snacking, shopping ... any or all. Plenty of shopping from discount to high end all throughout the area. Outlet shopping at huge Miromar outlet mall 15-20 minutes away. I think it's got everything you want. Also, if you play golf Naples is the golf capital of the US, with more holes per capita than anywhere else. If you fly in, check flights to Fort Myers. Might get cheaper flights and cheaper rental car by flying into Ft. Lauderdale or Miami ... about 1 1/2 to 2 hours away.

Take a look at Englewood. Very quiet, but has just about everything you're looking for. There are motels on the beach on Manasota Key, most with pools. These motels are small - not your highrises - and not fancy. But they're clean and the one at the end of Manasota Key that I stayed at had a kitchenette. The Englewood/Venice area is full of excellent restaurants, and the beaches all connect so walking the beach after dinner to watch the sunset is popular and beautiful. In fact, there are two very good restaurants across the street from Englewood Beach where you can watch the sunset. Also, the walk from there across the causeway to Rt. 776 is beautiful with several places where you can stop and watch the dolphins up close. Large shopping malls are limited, but if you are willing to take a little ride you can easily find them within 30-45 min. Englewood and Venice have several smaller shopping centers.

I have a home in the englewood area and do like it obv. But not sure the food is up to the standards of elsewhere that I mentioned. But it does tend to be better value too.