May is the month locals quietly hope tourists never figure out. The water hits 80°F, the snowbirds have left, prices drop 20–30%, hurricane season hasn't started, and the Songwriters Festival fills the bars with name-on-the-radio acts you can hear three feet away.
Weather
Highs 84–87°F, lows 75°F. Water 80°F. Rain: a few brief afternoon showers. Stone crab season ends May 1 (last call for claws). Hurricane season starts June 1, so May is the last quiet month.
What's happening
Key West Songwriters Festival (early May, free shows in bars all over Duval). Cinco de Mayo at Mexican spots. Mother's Day brunches at Latitudes and Louie's Backyard.
What to book
Sunset sails are easy to walk on. Snorkel trips have wider availability. Sandbar trips are perfect — water is warm enough to swim all day. Hotels run 20%+ off summer rates from mid-May.
Is it busy?+
No. Mother's Day weekend and Songwriters Fest weekend are the only real spikes. Otherwise it's the calmest month before summer family season starts in mid-June.
Is it hot?+
Warm but not brutal. The trade winds keep it comfortable. By July it's heavier — May is the sweet spot.