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Fall Guide to the Florida Keys

HomeAbout the AreaSeasonal GuidesFall Guide to the Florida Keys

The Florida Keys could be considered the land the other seasons forgot, offering the feel of summer year-round, and if you are not quite ready for what lies on the other side of your favorite season, a visit to the Keys could be a truly excellent idea. Offering warmth, sunshine, and less rain than you would normally experience in the true summer months, the crowds lessen in the fall and the locals come out to play, with some of our favorite events occurring during this time months! This guide to a carefree Florida Keys fall vacation and a stay in our RentTheKeys seasonal sanctuaries will soothe your summer seeking soul, giving you a little something extra to look forward to in the days, weeks, and months that lead up to your autumn adventures.

Florida Keys Fall Seasonal Events

Fall is when two of our favorite holidays take place, and because the mercury does dip a little during this wonderful season, getting outside and taking part in these Halloween and fall events will make this vacation unforgettable.

Mid-Cape Fall Fest in Cape Coral

The build up to Halloween can be our favorite part of the celebration, and the Mid-Cape Fall Fest, held at the Mercola Market of Cape Coral, is one your entire family will love. Held the second week in October and offering a pumpkin patch, costume contest, bounce house, live music, craft market, and food trucks, this first event of the fall season always gets us in the mood for Halloween.

Pumpkin Festival, Hunsader Farms in Bradenton

For over 30 years, Hunsader has set aside three weekends in October for their much beloved Pumpkin Festival. Offering everything that makes this beautiful season exciting, the list of what they offer is so long, it is simpler to say what fall related activities are NOT offered. (Absolutely none!) There are pony rides, hayrides, and train rides big and little, and there will be live music, good food, homemade ice cream, pumpkin pie, arts and crafts vendors, live shows, and a Pioneer Trades Village. There are sure to be some very exhausted tiny travelers at the end of your visit!

Oscar Scherer Halloween Haunted Trails in Osprey, Near Sarasota

Located just 12 miles south of Sarasota, Oscar Scherer State Park in Osprey is the scene of the most spooktacular haunted event. Generally occurring in mid-October, the event offers a nighttime adventure in scares with its Haunted Trail (older children only), a Haunted House that again is so frightening, we suggest only older children should attempt it, a Trick or Treat Trail that helps younger kids feel included, and a concession stand, because food is always the answer!

Siesta Key Crystal Classic in Mid-November

There really are numerous events taking place in the fall months. Our towns, islands, and keys come alive at this time, and while we insist that you enjoy a simple day on the white sand beaches of Siesta Key at least once during your stay, the Siesta Key Crystal Classic, an International Sand Sculpting Festival, will encourage a second visit. 24 sand sculptors from all over the world flock to our doorstep to compete in this competition, creating masterpieces you won’t believe are made from sand, while also offering sand sculpture lessons that will help your own sandcastle construction sessions be more impressive.

Warm Mineral Springs Park, 12200 San Servando Avenue in North Port

For our North Port fall visitors, spending a day in Warm Mineral Springs Park can bring a world of adventure to families and friends alike. Offering natural springs with an average temperature of 85 degrees it is especially fun to soak in the waters on cooler days, but a soak in these waters will be enjoyable at any time of the year, including fall. The history of Warm Mineral Springs Park reaches back thousands of years and is the spot of an ancient Native American burial site and fossils dating back to the Pleistocene Epoch have been discovered here as well.

Owen’s Fish Camp, 516 Burns Court

We can’t finish up a story on the adventures you will enjoy during your Florida Keys vacation without mentioning the food that makes our seasons more sanguine. Surrounded by Gulf waters, you might expect that seafood restaurants are plentiful in the area, and you are exactly right! We love our seafood, and nearly every restaurant you stop in will offer the freshest and sweetest, but if you want an authentic seafood experience, fun times and delicious foods await you at Owen’s Fish Camp in downtown Sarasota. Easy to find due to the old banyan tree out front, the tire swing out back adds to its charm.

Fall Adventures with RentTheKeys

Your most comfortable adventures will take place in our seasonal sanctuaries, the ones you will make your own. Contact us to reserve your favorite property today for an unforgettable fall in the Florida Keys!