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Haven't yet been to Key West, but given what I know about it, I'd say it wins in weather, beaches, and better to vacation in. I think Charleston takes the rest.
I think Key West wins for weather too. Water is prettier and warmer, but the Keys aren't known for their beaches, so I'd tie it with Charleston's long sandy strips of coast.
Yes it is not well known but the keys don't actually have great beaches. Bahia Honda is the closest to being a decent one (and it is a very beautiful beach... to look at), but it is still covered in seaweed about 20 feet out, so you can't go deep without getting icky toes. There are artificial sand beaches on Key West. The rest are covered in sharp coral for the most part. Beautiful to look at, and great for taking a boat out and diving in, but the beaches themselves are not the most fun to wade in.
The Florida barrier islands have better beaches, along with some of the islands off the coast of Miami.
I have been told recently that Charleston beaches have brown, murky water, in which case maybe not. I wouldn't know, having never been there. Care to dispute that?
Charleston. Key West sucks. It's too small and expensive. Never come here.
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