Hi - I'll let DH respond to this one as he just got back from his second trip in a year to Key West.
I just returned yesterday from Key West. Took my 15-year-old son along.
Key West is not known for its beaches, so its not a big consideration for me. The Wyndham (stayed there last year) has a decent beach but its pricey. I stayed at the Comfort Inn on Roosevelt Blvd. this time. About 10 min. from the action, but decent rooms and a nice pool. The Radisson next door is also good. Theres a shopping center nearby with a grocery store, T.G.I. Fridays, Outback, and other fast food places.
Good downtown restaurants at reasonable pricesDuffys Seafood House, Camilles (great breakfast, Diner Shores (breakfast), Hard Rock, Louies Back Porch Grill. Theres even a Dennys in Old Town if thats your style.
Dont miss the sunset at Mallory Squarego an hour early or have dinner in the Cuban restaurant inside the cigar factory museum. Be prepared for a wild show on the squarenot too offensive; really lots of fun.
Duval Street: There are bars on every corner and tee shirt shops everywhere. Some of the shirts may be offensivenothing my son had not seen before. Go in the late morning or late afternoon when its not so hot and not so crazy. Only go at night if you dareits insane. Most people are just having fun and wont bother you, but they may be a little tipsy. Most merchandise is expensive, especially anything that says Key West, but you can bargain a little with some store owners. If you see something you like, shop around a littleyou may find it cheaper elsewhere.
Hard Rock is great for lunch. Dine outside and do some people watching, then buy the kids a tee shirt.
Dont missAquarium, Truman Little White House, the Chicken Store (my favorite), Hemingway House, Southernmost Point. If you have the time (and money), take a catamaran out and do some snorkeling on the reef.
I rented a car, but you can take the Bone Island Shuttle, which will take you anywhere on the island. You can buy a weekly pass that is a good deal. You could also rent bicycles or mopeds, but theyre expensive. There's a trolley too that's very good.
I have fallen in love with the island, but it sure aint Disney World. But it is a very unique placecrazy, funny, friendly, carefree, and tropical.
Rentals and condos are VERY expensive. If you have not been there before, stay at a hotel. The island is small enough that you're never very far from anything.
Let me know if I can answer any other questions.
DH