Minnie, Key West timeshare availability is the toughest in the country to get into. This may be a moot point because I would check Key West availability first.

Q.Any preference for staying on the Gulf side or the Atlantic side. Or any recommendations

Duval street is 1.25 miles in length and unless you want to go over to Smathers Beach, which is a nice place to walk in the morning, you can stay in three areas and be close to everything.

The north side. This is where the big hotels are - the Hilton, the Ocean Key, the Pier House, the Hyatt and the Galleon. The Galleon is a time-share. The Pier House (where I stay) is 1 Duval, the Ocean Key is 0 Duval. The Key West Bight is a 5 minute walk clockwise, and the Mallory Docks is the same counter-clockwise.

The South Side, and this is getting to be more popular. I'm not aware of time-shares there, but places like La Mer, the Dewey House, the Southernmost houses (a generic name for 4 motels)all are getting good reviews. There is a small beach there and the Duval Beach Club right at the end of Duval.

Anywehre else just off of Duval. The Simonton, Caroline area is particularly nice, but if you stay on any side street off od Duval or Simonton, you will not be far from anything.

Pjk

Basically you will want to stay in anywhere that is in an area called Old Town. It is the historic area of Key West and much more interesting than the other area, New Town. You will also really not need a car if you stay in Old Town so that is another plus.
The gulf side is a tad bit nicer compared with the Ocean Side and it also has much more activity including the sunset celebration.
Here is a site that I use quit a bit when planning a trip to Key West. I hope this helps.
http://keywest.com/newbigmap.gif

We love to take the Casino Ferry from Naples or Ft Myers - it's a fun trip and no traffic !

I've deposited my week and have put in a request for Key West next February. I'm thinking positive for now, so when I get the confirmation I'll be asking more specific questions about the area. We've traded to go to Maui before and that too is a tough exchange. So tough in fact that we bought a timeshare there too just to stop the hassle of trading to get there.

Does anyone know anything about the ferry from miami to key west?