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Why Visit the Keys During Winter?

At first glance, the question above proves to be a little unusual, especially as everyone KNOWS why you should want to visit the Keys during the winter, but that’s ok! On the off chance you haven’t given much thought to a Florida winter break, we have created this guide to all the wonders that make the Keys one of the most beloved winter travel destinations. Offering amazing weather, beach days that never end, and the opportunity to work on your winter tan, the only thing better than all the fun we have in store for you during your seasonal getaway will be coming home to the comforts, luxuries, and style of our RentTheKeys vacation escapes! We love winter down south, and if your home is from a much more northern region, we know that you will rediscover your love of the season after experiencing at least one week without snow, sleet, or ice with a Florida Keys winter!

Can This Be Real?

Many of us at RentTheKeys have migrated from much colder climes, and if we didn’t live here, we would not be able to believe how incredible weather is during winter in the Florida Keys! With highs in the mid-70s to the low 80s, and a much dryer climate than is standard in the summer, every day is better than the one before! Wake up each morning and watch the sun rise as you walk along the beaches, spend your days soaking in the rays of the sun, and end each evening enjoying a fresh seafood meal on the patio of our local restaurants, watching the sun sink into the sea in an explosion of color. Grab your camera and snap away at the flora and fauna you encounter as you hike along the Charles Hegener Memorial Nature Walk in Sarasota or stick close to home and swim in the private heated pool that came with your RentTheKeys seasonal sanctuary!

Annual Christmas Parade, December 4, De Soto Square Mall in Bradenton

Everyone knows that the calendar doesn’t really dictate the changing of the seasons and as Mother Nature wreaks havoc in your real life, a very late fall excursion to the Keys and an opportunity to watch the Bradenton Annual Christmas Parade can make it all better! Consisting of local Jeeps and drivers, this unique parade has been a Bradenton tradition for years and when you see the parade of jeeps all decked out in their holiday finest, your holiday spirit will be immediately amp up a notch or two!

Sarasota Winter Fine Arts Festival, January 8 & 9, JD Hamel Park in Sarasota

Once the holidays end, the gray gloominess of winter can really get you down and when your spirit needs some perking up, Sarasota in January does the job! The Sarasota Winter Fine Arts Festival is our favorite ways to while away a January weekend, as it features art in every variation you can imagine! From paintings to sculpture and jewelry to clothing, this annual festival is destined to be filled with all the things you never knew you needed!

Cape Coral Farmers Market, Saturday Mornings, SE 47th Terrace & SE 10th Place

Colder weather states see the end of farmers’ markets with the first snow, but in Cape Coral, our farmers’ market lasts year-round! Spend a lazy Saturday, roaming the aisles seeking the freshest produce, the sweetest baked goods, and the perfect gifts for family members who weren’t lucky enough to accompany on this wonderful journey during winter in the Florida Keys! And if you are wondering whether or not Florida oranges are as sweet and juicy as they are portrayed in all the commercials, the farmers market offers the opportunity for you to taste test them yourself!

Sarasota Blues & BBQ Festival, March 4 at the Robarts Arena

As spring takes its own sweet time to arrive, the end of winter can seem like it will never take place, making a Sarasota escape in March your newest obsession, especially when you realize that the Sarasota Blues & BBQ Festival comes to town on March 4! Offering live music, amazing barbecue, and the opportunity to experience the most perfect month of the year (in Florida!) NOW is the time you should start thinking about reserving one of our Sarasota Rent the Keys seasonal sanctuaries!

Sarasota Holiday Boat Parade of Lights, December 11 at Sarasota Bay

This annual tradition, first started in 1986, brings thousands of spectators to the shores of Sarasota Bay to view a parade of beautifully lit boats as they make their way from City Island across the bay to Centennial Park, south under the Ringling Bridge and beyond. Bring a lawn chair to one of the viewing areas—Centennial Park, Bayfront Park, or City Island are good choices—and enjoy the hour-long spectacular beginning at about 6 PM.

Come Play with RentTheKeys This Florida Keys Winter

As if all the fun activities and adventures we have been talking about was not enough, you still have the magic of our RentTheKeys winter homes to look forward to! Sleep late in comfortable beds, sip wine as you watch the setting of the sun, and revel in wearing flip flops and bathing suits in FEBRUARY! Although you won’t be able to live forever in this winter paradise, we hope that your time in the sun helps you make it through the rest of the winter. Reserve one of our vacation homes or Florida Keys winter!