The discussion below was copied from the Net's "Ask Your Neighbor" page (/ask_your_neighbor/ask_your_neighbor/).

We would appreciate suggestions on where to stay in the Keys next Winter.  We’ll need a slip for a 42’ boat with a four foot  draft and will probably want to haul the boat and have the bottom cleaned.  Our initial thought is to rent an apartment for a few weeks but no longer than a month.  The apartment does not have to be on the water but does need to be within easy bicycle range of the marina. We hope to find quiet, reasonably priced,  locations and are willing to make a commitment now to hold a good apartment and a good slip.
Dave and Pam Feltner

Islamorada, Plantation Yacht Harbor. Great we have stayed there for years.  Now fully rebuilt docks $21.00 foot park you car at the boat. pyh.com
Bob

This is our first winter in the Keys. Right now we are in Marathon at the Sombrero Marina and Dockside (305) 743-0000. This is a good start for us, the price is good for the month, we have a 66' with a four foot draft. There is plenty of water here. We plan on exploring so being at mile marker 50 makes it easy. There are plenty of bike paths, shopping, golf course, and a lively Dock Side Tiki Bar and Lounge with live music. Good places for breakfast, lunch and dinner in walk/bike distance. The Marathon Airport is two miles away with every car rental  Nice, friendly people. If you are looking for laid back, this is the place. Very quiet during the day, the music generally dies down around 9:00 pm. Nights are quiet. Just down the road from the this Marina is another one, Sombrero Resort and Lighthouse Marina, they have condos for rent, don't know much more than that. Best of luck with your search. The Keys are beautiful.
Karen and Denny