Coming to Key West at the end of April from the SF Bay area. We did a similar trip 20 years ago and flew into MIA, stayed somewhere nearby and then spent 2-3 nights driving down the keys with a stop at Everglades National Park. Stayed at a lovely spot on the beach on Islamorada (which of course I don't remember the name of, it was before TripIt and can no longer find anything like it online). Traffic once we left the Miami area the traffic was fine, and we had a lovely drive to Key West over the next couple of days.

Can anyone advise on the idea of repeating this plan? Where I live the traffic that was "fine" 20 years ago is a nightmare now, so is planning on a peaceful drive may not make sense (?). We are likely to land MIA in the mid to late afternoon potentially on a Friday. Should we just stay near the airport? And a real long shot: any ideas about older style motels that could still have sunset views and be fun in Islamorada? .
[It isn't so much a cost issue but that whole area had a by-gone era feel to it that we really liked. Much like Palm Springs. Not really interested in an upscale place we could get anywhere.]