We spent January in Naples, 1 rainy day and 1 cool week, never did turn on the heat but we are from MI - wore shorts even on the cool days. We had 3 great weeks of weather - warmer than normal. Naples is very nice but pricey. No sign of damage that I saw. Not sure about hotels but airbnb type lodging would be hard to find - I think - unless you are looking a year in advance. Traffic is a pain - we try to book superior locations - hopefully can walk to beach and food and avoid driving. The nice thing about staying for a month is you figure out the shorts cuts so to speak and save some time and frustration. Have spent a time in Fort Myers Beach - not but congested. Prefer between Clearwater Beach and St Pete's Beach - less pricey, lots of beach and stuff.