There’s never a bad time to vacation to Key West, but there’s something special about visiting in winter. There’s just as much to do in Key West in the wintertime as any other season. While the temperature drops from the summertime highs to a milder climate, the crowds also tail off, creating a pleasant vacation experience. 

5 Reasons to Plan a Winter Getaway to Key West

At Compass Realty, we highly recommend taking a winter vacation in Key West. To give you the extra push you need to book your winter getaway, we’ve created a list of five reasons to visit Key West in the winter.

Warm Temperatures

Though temperatures dip in the winter months, Key West’s climate is still much warmer during this time of year than other destinations. During the winter months, temperatures typically stay around 75-80 degrees. So while you might not feel as comfortable going swimming as you would in summer, the weather is still ideal for biking, paddling, beach walks, and many other outdoor activities.

Smaller Crowds

With children back in school, family vacations to Key West tend to drop off significantly in the winter. When the large crowds dwindle, you have a better chance to get the real Key West experience. Beaches, parks, restaurants, and all of the other great places you want to visit will feature fewer lines and crowds. Overall, fewer crowds make for a better vacation experience. 

Winter Events

Even in winter, there’s always a fun event going on in Key West. For example, the lighted boat parade takes place in December and is a festive way to celebrate the holiday season. There’s also the Mile 0 Fest, a music festival that features a fantastic mix of talented musicians. No matter what your interests are, you’ll be able to find a winter event in Key West that appeals to you.


Are you itching to get out and play a round of golf? Key West is still a premier golf destination in the winter. Bring your clubs and hit the links at Key West Golf Club, a Rees Jones championship course. There aren’t many places where playing golf is as good in the winter as it is in the summer, but Key West is one of the few. 

Duval Street

No matter the weather or time of year, Duval Street is always fun. This street is world-famous and is known for its fabulous nightlife. Get in on the good times at the legendary Sloppy Joe’s, which has roots going back as far as 1933. No matter where you decide to go, you’ll find plenty of drinks and live music on Duval Street. 

Key West Winter Vacation Rentals

A vacation rental in Key West in the winterKey West is a fantastic vacation destination, even in the winter. If you’re planning a fantastic winter getaway to Key West, consider staying in one of our well-appointed vacation rentals. We have vacation rentals in great locations in Key West, including Key West Golf Club and the Truman Annex. To learn more about our rental options, check out our website or give us a call at 1-305-292-1881.