It is the perfect place to call ahead to have your bike pick ready. The best for my money rental shop is Eaton Bikes. They specialize in bicycle rental, sales and maintenance and that's it. It's a low-key shop where you can pickup a rental and be in and out in less than five minutes. That's all they do is help you with rental bikes for touring. It's a great, cheap way to explore the island from ground level.
Taking advantage of the bike rentals was a really good idea down here in Key West. I think the way to go in this city is on a fat tire bike with electric assist. The standard bikes are great for men, women, children and tandem bikes. I don't think I would do a tandem bike down here they're just so much going on, it is better to have a single bike for maneuverability. The tandem bikes might be really good for something like a wedding or a special event where the bride and groom were going to drive up in it or leave using it. All the bikes come with the front headlight and rear red light, the blinking kind so you can go for nighttime rides. I love going by Smathers Beach at night, which is a nice ride and really breezy.