I would definitely visit the Little White House that was used by Pres. Harry Truman several times as a getaway while he was president. Up until at least Pres. Clinton's term in office, this house was still used occasionally by presidents to host special events.
If you stay close enough to Duval Street you won't even need to rent a car. I believe Halloween is a big deal in Key West, and prices for hotels go up quite a bit right before Halloween. When I went to Key West a few years ago, it was a couple of weeks before Halloween, and the person running the B&B I stayed at remarked how much hotel room rates go up at Halloween.
There are lots of B&B's in Key West. If you have issues with climbing stairs (which I don't), that may be something to consider. I would definitely go back to Key West again -- very enjoyable.
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