Are you planning to timeshare trade, or private accommodations? If private, we really liked Southernmost Point Guest House, it's a historic b&b inn, IMO great location, free parking, and "reasonable" for Key West. That'd be my first choice if/when we go back, altho I'd also considered a motel-type place that has houseboats. Also really liked Fort Zachary Taylor State Park for beach time, as others have mentioned. Enjoyed Mel Fisher museum (not to be confused with the other shipwreck museum), and the butterfly house which is next door to the inn I recommended. Restaurant-wise, I was personally disappointed with a couple of Cuban places we tried, liked seafood meals better but can't recall restaurant names. We booked our Key West trip sort of last-minute, after hurricane Ian undid our Sanibel reservations, and was glad to salvage a decent vacation.