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Reservations or "wing it" in Key west?

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We are traveling (two couples) into Ft. Lauderdale, renting a car and traveling the Keys leaving the 19th -24th of April. Our question is: should we reserve before we go or drive and find places to stay? This is a first for all of us, we don't need a fancy resort, but want comfortable, clean accommodations. We are hoping we can find reasonable prices along the way. We just thought it would be more fun to "wing It" but are concerned at the listed prices. We would probably spend at least 2 nights in Key west, and the other 2 somewhere along the way. Any recommendations would be appreciated.

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