Having lived in Key West for awhile and seeing your wife suggested or has seen the Waldorf as an option I think you are going to be somewhat disappointed with the middle keys accommodations.
There is much more to Key West than Mallory square and Duval street
Restaurants are exceptional
Michaels
Cafe Sole
Prime 951
Antonia's
Seven Fish
Cafe Marquesa
Etc
All within walking disance of old town Key West
There are
bike tours
trolley tours
walking tours
aquariums
butterfly exhibits
shipwreck museums
shopping
and beaches in Key West (albeit imported from the Bahamas)
The middle keys are great but you won't find accommodation that compare to the Waldorf nor will you be able to do anything with out driving around.
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