City with downtown vacation rental
 

We are looking to rent a condo for a month or 2 in January February Mar of 2017 that is in a city near the beach. We want to be able to walk to restaurants, shops, etc. and we are looking anywhere on the east coast of FL and south of Clearwater.

We used to live in the heart DC and then Portsmouth NH. We now live outside of Boston but not in any walkable city/town. We would like to get some of that back and avoid some of the winter by looking in Florida. We are not wed to Florida but it is a place to start.

Price would be 3k to 5k a month. There would be the 2 of us plus 2 cats.

I am starting to look at towns now and we have spent time in many on the west coast but not so much on the east coast.

Any insight would be appreciated.

Key West would be my pick...

Key West is a great pick. Sarasota has a walkable downtown, but you can't walk to the beach.

Outside of Florida, how about Charleston or New Orleans?

#1 Key West (Truman Annex area)
#2 New Smyrna Beach
#3 Fernandina Beach

I'm very confused. You say "east coast of Florida" and then state "south of Clearwater" which is on the west coast of Florida. Which is it? Sorry, but frankly the biggest issue is the two cats. Not impossible, but difficult.

I've never had trouble finding a VRBO that accepted cats.

Miami Beach