Best Times to Visit Key West
The best time to visit Key West is between March and May. The winter crowds will taper off, the hotel rates become reasonable, and the weather is remarkably similar to winter's blissful 70s and 80s. Speaking of winter -- that season is the island's busiest and priciest. The rainy and humid summer months see the fewest tourists but the best hotel rates. The trade-off might be worth it, but you are still gambling against hurricane season (June to November). Also, beware that rates will surge during special events like PrideFest Key West and Fantasy Fest Carnival.
Summer showers deters visitors, but room rates attract them. If you can stand the rainy season (with high 80s and low 90s), pack an umbrella and enjoy Key West's nonconformist nature for cheap.
At this time, hurricanes come and go; therefore, most tourists head for higher ground. But bargain hunters should watch the rates and the weather forecast to snatch unbelievable deals.
Can you put a price on ocean views and mid 70s in the dead of winter? Hotels here can -- a high one. The holidays (combined with the end of hurricane season) mean an instant influx of visitors.
Key West sees clear skies and climbing temperatures in the spring (it'll be in the mid 80s by May). Too isolated for most Spring Breakers, this is the prime time to take advantage of the beach and the rates.