The Best Time to Visit the Florida Keys

Wondering when to pack your bags for the Florida Keys? That all depends: There are plenty of reasons to visit our beautiful island community throughout the year. Whether you plan on a low-key fall getaway or a fun-filled spring break, you’re sure to have a memorable stay whenever you visit.


Starting in September, island life becomes even more relaxed—yes, it’s possible—making the fall a perfect time for a relaxing couples retreat or a weekend trip with friends. The most serene season in the Keys brings with it beautiful weather, quieter crowds, and some of the best rates at Cheeca. Plus, if you’re looking for a bit of excitement, you can plan your stay during Key West’s annual Fantasy Fest.


It’s the high season for a reason. Once January rolls around, residents of colder climates are craving sun and sand, and the Florida Keys offers both in abundance. As the ideal spot for a post-holiday vacation, the Keys feature pleasant winter weather with little rain and comfortable temperatures. Stay at Cheeca and discover a picture-perfect oasis from which to soak up the scenery.


Spring break brings warmer temperatures, special island events, and an added buzz of excitement. If you’re worried about college crowds, fear not: Here in the Upper Keys, we offer a more family-friendly atmosphere. As a premier resort in Islamorada, Cheeca invites guests of all ages to partake in our many on-site offerings, including golfing, beach volleyball, watersports, and much more.


The summer months mark the start of the off-peak season in the Florida Keys. However, while the crowds start to thin out, there are still plenty of local activities and attractions to be enjoyed. If you’re a Florida resident, you can escape to the islands and delight in slightly cooler temperatures. And, if you stay at Cheeca, you can add luxury accommodations, delicious dining, and on-site entertainment to the mix.

No matter when you choose to visit, you can enjoy the best of the Florida Keys throughout the year at Cheeca Lodge & Spa.

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