Are you considering booking a stay in Key West this winter? Great choice! Allow us to tell you about Key West winters with superb places to stay in our Key West luxury rentals, as well as fun Key West events, and a bit more. Stick around to learn all about Key West before you visit us this winter!
Mild Weather
Key West in winter comes with beautiful weather and plenty of opportunities to do more outside. The temperature average changes by month here, of course. Every month of this beautiful winter season presents something new and unique from the others, starting with December and January. In December, highs of 78 degrees and lows of 69 degrees Fahrenheit are super common. So, expect to get nothing less.
In January, it is worth noting that you can typically expect to see highs of 75 degrees to lows of 65 degrees Fahrenheit. But in February, just a month out from then, those numbers move to 77 and 68, respectively. In March, you are looking at 78 and 69, whereas, in April, you should expect to see 83 and 74. You can see how the temperatures start to creep up as you’re moving out of the winter months. If you can’t handle the extreme temperatures, you’re going to want to avoid the late spring or the summertime!
The winter weather makes this season an ideal time to plan your vacation in one of our family-friendly Key West rentals. In addition to the stellar mild weather you see, there are often many fewer people here vacationing. So, you get smaller lines and shorter wait times, too, and even some reduced fare costs in specific venues. Winter rules!
Winter Events in Key West
Yes, believe it or not, Key West has known annual events that take place only from December through April. So, if you want to know just a little bit of this here and take a peek at what some of those events might be, then keep reading. There are four events listed below to get you started.

Mile 0 Fest
Mile 0 Fest is one of the most popular events in Key West, bringing together dozens of artists to play some incredible Americana music. Numerous performances will be held all around the area each time this annual event is held, just as it’s been every year thus far. Tons of live music performers are there in person, and everyone seems to jam out to a good ol’ time. So, if this is your kind of thing, then don’t miss this event. It promises to be good!
This is typically an adult-oriented type of event, held in a massive amphitheater. Kids are allowed to come, but of course, an adult has to purchase a wristband pass for their admission, and they must accompany them at all moments of the event for safety reasons. In this festival, pets like dogs are not allowed, given the exception that they are service animals and proper documentation is provided upfront before entrance is granted.
Also, at this unique festival, all kinds of groups, from all sorts of cultures, get together to talk and sing and remember all things that make Key West as great as it is, not to mention its water culture (parasailing, beaches, jet skiing, etc.). In addition, if you are looking for a spot to park, there is plenty of available parking every year, usually both in the island’s main lot as well as at the amphitheater itself.
This year, Mile 0 Fest will be held from January 25 – January 29, 2022.
Annual Dachshund Walk
This adorable event is held annually on New Year’s Eve. Some think of it as an official “kick-off” to the new year. What to expect from this event you ask? More than 200 Dachshunds accompanied by their owners strut the street while spectators admire! If you’re in town, don’t miss your chance to experience this unique parade of puppies! Take pictures, cheer them on, or just admire, the choice is yours! At the end of the procession, don’t miss your chance to vote on which dog is the best dressed, most well-groomed, cutest overall, etc. This is an event true dog lovers will not want to miss!

New Year’s Eve
What more would you look for on a Key West New Year’s Eve than a celebration party to attend? It is hosted every single year and never fails to make headlines. It even gets coverage on CNN and ABC! Multiple other news outlets and broadcasters are there live to cover all sides of it, too. The people behind this great event like to mix things up and do something new every year. Often it entails something they did not do the year before; for instance, in 2011, they dangled a massive high heel shoe, and it swung overhead from one side of the balcony to the other. It was a bright, red shoe; Sushi, the n ‘diva’ to ride that shoe, got on it and celebrated the last few seconds of that year!
Neat, right? And what better way can there be to finish off the last few seconds of the year than to do something wild and crazy that gets captured on the local and national news sources?
Plan Your Key West Vacation
No matter which of our Key West vacation rentals you choose, you can rest assured that you’re getting the definition of luxury. Experience incredible amenities like high-speed internet access, huge living and dining rooms, flat-screen TVs, and so much more. Our Guest Concierge team is always here to help you finalize your options, and once you’re in town, you can ask any questions you might have about the area. Contact us now to get started planning your winter trip to Key West!
Your Key West Vacation Rental
For Key West rentals, Key West Vacation Homes is here. We have got the largest selection of Key West waterfront rentals, as well as a collection of Key West Rentals with a dock. Ready to dive in and book your trip? Give Key West Vacation Homes a call today!






