Winter in Key West: What to Expect
With plenty of sunshine, sandy beaches, and gorgeous tropical vacation homes available year-round, Key West is the ultimate all-season vacation destination. But when you’re looking to escape the cold during winter, there’s no better place to warm up than in the Florida Keys.
From beaches and boating to fun festivals and holiday events, Key West winters have it all. Ready to plan your perfect winter getaway? Here’s everything you need to know about visiting Key West during the winter!
Winter Weather in Key West
When it comes to weather, winter in Key West is pure magic! It’s cooler and more comfortable than in summer or fall, the rainy season and hurricane season are over, and most importantly, it’s still warm enough most days to enjoy the beaches, watersports, and outdoor activities the island is famous for.
Overall, Key West has mild winter temperatures that mostly linger in the mid to upper 70s during the day and upper 60s at night, with occasional warmer days in the 80s, and occasional colder days in the 60s. Rarely, a cold front might move in, bringing temperatures into the 50s, but these tend to only last a few days.
Winter Crowds in Key West
Like most of Florida, the winter season is also peak tourist season in the Florida Keys, with many aptly named “snowbirds” visiting from colder climates. But other than slightly longer lines at some restaurants and attractions, and typical holiday crowds, it’s all very manageable.
Early December is one of the calmest times to visit, with lighter crowds and a relaxed island atmosphere. Things liven up around Christmas and New Year’s, and from January through mid-February, you’ll find a pleasant balance of activity without the hustle of peak season. By late February and March, visitor numbers rise again as the island heads into its busiest months.
Winter Things to Do in Key West
Unlike many destinations that have to cease certain activities due to snow, all of Key West’s famous attractions remain accessible all winter long, even the outdoor activities and watersports. And trust us, with Key West’s near-perfect winter weather, you’ll want to be outdoors!
Here are some of the best things to do during winter in Key West.
1. Enjoy Beaches, Boating, and Watersports
With mostly warm, sunny weather, winter is a great time to hit the beaches or be out on the water in Key West. Enjoy kayaking, paddleboarding, boating, jet skiing, parasailing, and much more. And yes — you can still go snorkeling in the winter in Key West! For those colder days, you’ll have the option to rent a wetsuit, if desired.
You can also book glass-bottom boat tours to see marine life, sunset cruises, fishing charters, and many other eco-tours that are available throughout the island.
2. Spend the Day Strolling Duval Street
Lined with shops, restaurants, and attractions, Duval Street is the epicenter of fun in Key West! It’s where you’ll find famous bars, like Sloppy Joe’s, historic landmarks, like the Oldest House and Museum, famous attractions, like the Key West Butterfly and Nature Conservatory, and of course, Key lime pie shops on nearly every corner.
With warm, breezy winter weather, it’s the perfect time to spend the day on Duval Street strolling, shopping, browsing art galleries and attractions, and enjoying food, drink, live music, street performers, and more.
3. Go Hiking or Biking
Winter is the perfect time to enjoy a leisurely walk, stroll, or bike ride in Key West. The city has plenty of parks, beaches, nature trails, and green spaces, full of scenic views and local wildlife. And of course, most city streets are pedestrian and bike-friendly. With sunshine and cool breezes, winter is the perfect time to explore on foot or rent a bike and cruise along the beach.
4. Take a Walking Tour
Winter’s reprieve from the heat offers a great opportunity to take advantage of some of Key West’s famous walking tours. From exploring the island’s rich history to eating your way through all the best cafes and bodegas, you’ll find a walking tour that suits nearly everyone. There’s even haunted pub crawls, ghost tours, and more.
5. Take a Day Trip to Dry Tortugas National Park
Home to the historic Fort Jefferson and crystal-clear waters, perfect for snorkeling, Dry Tortugas National Park is just a hop, skip, and jump away from Key West — or should we say, a quick ferry or seaplane ride away. And while it’s accessible year-round, winter’s near-perfect weather makes it a great time to explore this hidden gem.
Winter Events in Key West
From holiday happenings to food festivals, Key West has some great winter events in the lineup!
December
Holiday spirit meets tropical sunshine in Key West each December. The island comes alive with festive lights, lively parades, and an unmistakable sense of celebration — all set against balmy breezes and palm-fringed streets.
From local bars decked out for the season to lighted boat parades gliding through the harbor, December in Key West is where island charm and holiday magic meet. And when New Year’s Eve arrives, Duval Street turns into one of the most spirited countdowns in the country, complete with the famous Conch Shell Drop outside Sloppy Joe’s Bar.
Can’t miss December events in Key West:
- Key West Holiday Fest – A month-long celebration featuring parades, light displays, and festive markets.
- Lighted Boat Parade – Watch a fleet of brilliantly decorated boats sail through the Historic Seaport, a local favorite.
- Holiday Lights Trolley Tours – See the island sparkle from the comfort of the Old Town Trolley, complete with holiday tunes.
- Key West Art & Historical Society Holiday Bazaar – Browse local artisan goods and festive treats at the Custom House Museum.
- New Year’s Eve on Duval Street – Choose your countdown: the iconic Conch Shell Drop, the Drag Queen Red Shoe Drop at Bourbon St. Pub, or the Pirate Wench Drop at Schooner Wharf Bar.
If you’re visiting in December, be sure to check out the Key West holiday calendar to see what festive adventures are in store.
January
January in Key West is all about creativity, rhythm, and a burst of New Year’s energy. The island’s slower pace meets an inspiring lineup of events that draw writers, runners, and music lovers from across the country. Whether you’re diving into a thought-provoking author talk, chasing a runner’s high along the waterfront, or swaying to the sounds of live Americana under the stars, January offers the perfect mix of culture and coastal fun.
Top January events in Key West:
- Key West Literary Seminar – A renowned multi-day festival featuring readings, panel discussions, and workshops with celebrated authors and poets.
- Key West Half Marathon & Runfest – Run (or cheer!) through the island’s most scenic routes, from Old Town streets to oceanfront views.
- Mile 0 Fest – A five-day celebration of Americana and country music, with top artists performing across intimate venues and outdoor stages.
February
February is all about festivals in Key West! Seafood lovers can sink their teeth into lobster, crab, conch, fish, and other fresh catches at one of the island’s most anticipated culinary celebrations – The Florida Keys Seafood Festival. Arts and crafts enthusiasts can shop for one-of-a-kind artwork, pottery, jewelry, and handmade treasures at a beloved local market that fills Old Town with color and creativity.
And for the bravest of souls, there’s even a quirky island tradition that invites you to take a dip in the Atlantic — don’t worry, the water isn’t that cold!
Top February events in Key West:
- Florida Keys Seafood Festival – Feast on fresh local favorites like lobster, crab, and conch while enjoying live music and ocean breezes at Bayview Park.
- Key West Art & Craft Festival – Shop for unique, handcrafted pieces from local and regional artists — perfect for finding a true island keepsake.
- Southernmost Polar Bear Plunge – Take the plunge for fun and charity, proving winter in Key West is nothing short of tropical adventure.
Packing for Key West in Winter
Ready for your Key West winter vacation? While you can leave your coats and boots at home, we recommend packing a few essentials to make the most of your time on the island.
- Bathing suits/beachwear
- Flip-flops and/or water shoes
- Supportive sneakers, sandals, or other comfortable walking shoes
- Casual clothes for daily wear and outdoor activities
- Light jacket and pants for chillier evenings
- A few dressier pieces, like sundresses or linen pants for upscale dining or holiday events
- Sun protection, such as hats, sunglasses, and reef-safe sunscreen
- A light jacket for chillier mornings or evenings
- A small tote bag or backpack to carry your essentials at the beach or while sightseeing
- A waterproof phone case (preferably with a floatie)
Don’t have all of these? Don’t worry! Key West has tons of great shops where you can find anything you might need.
Winter in Key West: FAQs
Is winter a good time to visit Key West?
Yes — in fact, winter is one of the best times to visit Key West! The weather is perfect for outdoor activities, with no potential threat of tropical storms during this season, and tons of fun events happening.
Where’s the best place to stay during the winter in Key West?
Winter is peak season for Key West, so hotels are typically more crowded than usual. To enjoy a relaxing winter getaway, we recommend staying in a private vacation rental.
The first two weeks of December offer a quieter pace and fewer crowds, making it an ideal time to visit before the holiday rush. Activity begins to build around Christmas and New Year’s, while January and February bring steady, moderate crowds across the island. By late February and March, visitor numbers rise again as Key West enters its lively peak season.
Book your nightly winter stay with Vacation Homes Key West to enjoy all the comforts of home in a fully furnished rental — and if you’re dreaming of a longer island escape, explore our monthly rentals like Sun, Sea & Citrus. Nothing beats unwinding in your own private hot tub under the stars on a cool winter night.
Are the beaches swimmable during the winter in Key West?
The beaches in Key West are typically warm enough to swim, even in the winter months, with water temperatures typically in the mid-70s. However, during the occasional cold front, some might find the water to be a bit too cold for comfort.
Can you go fishing in Key West during the winter?
Yes, winter is a great time for fishing in Key West (and in the Florida Keys, in general). Cooler water temperatures bring in a host of migrating species, such as sailfish, King mackerel, tuna, and more, so there are plenty of opportunities to reel in some fresh seafood!
Plan Your Perfect Winter Vacation in Key West
Ready to swap snow for sand this winter? With endless sunshine, beautiful beaches, and lots of fun things to do, Key West makes for the perfect winter getaway.
Book your stay with VHKW and enjoy fully-furnished vacation homes with premium amenities like pools, outdoor living spaces, beach gear on site, and stunning ocean views, just minutes away from all the best winter events and attractions in Key West!
