The year-round sun and warmth of Florida make it the ideal destination any time of year you need a break. Pack your bags and gather your friends and family for a fun and exciting fall vacation full of sand, water, and sun, as well as some fun indoor activities for when there’s a little chill in the air. Set your sights on the Florida Keys and Sarasota and their many exciting offerings, and you’ll build one of the best Florida fall vacations to keep you happy and busy throughout your stay.

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Anna Maria Island Historical Museum

Take some time out of your busy schedule of fall activities to learn about one of the area’s barrier islands. The Anna Maria Island Historical Museum on nearby Anna Maria Island is loaded with history and treasures from the locale’s past. Visit the old city jail, now an Anna Maria tourist spot but previously the actual city jail that was in use until the 1940s. Learn about the many Hollywood movies shot in the area, like Palmetto and The Perfect Storm, and even early life on the island dating all the way back to 700 AD and evidence of Native American cultures.


A Sarasota-area vacation without a visit to its beaches, no matter the time of year, is virtually unheard of. Pack up your group and your beach gear and make the short trip to the sand. While taking a dip in the shimmering waters of the Gulf of Mexico may be a bit chilly, there are plenty of things to do on land, including taking a walk, sitting and soaking up the sun and read, or watching the kids build sandcastles. Whether you choose one of our rentals in Sarasota or surround yourself with water on one of the keys, the many area beaches are a top priority for any family getaway.

Festivals and Fairs

Each one of the Florida Keys, as well as mainland towns like Sarasota, celebrates fall in its own way. Check with the local chamber of commerce or event organizers to find out what special things may be going on. From Oktoberfest and fall harvest and local arts and crafts fairs to special island celebrations like Anna Maria Island Bayfest, there will be plenty of fall flair to enjoy on your Sarasota getaway.

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For the golfers in the group that want to golf near the Gulf, you can set sail with your clubs to one of the two courses on Longboat Key or have the only water you encounter to be the water hazards on the courses around Sarasota. Make tee times at Sarasota courses like Stoneybrook, the Meadows, and TPC Prestancia. The island courses both call the Resort at Longboat Key Club home. Links on Longboat and the Harbourside course are both challenging courses that not only bring on-course water and sand hazards into play but potentially the waters of the Gulf, too!

Bicycle Rentals

Like on many islands, there barrier islands of the Sarasota area have several places that a motor vehicle can’t go. Instead, explore the many walking and bike trails that let you see the sights of the Florida Keys during fall. You will find a bike to fit the needs of each group member, like cruisers, tricycles for added balance and basket space, a romantic bicycle built for two, and even children’s bikes and adult bikes with baby seats. Many rental companies provide complimentary locks and baskets with your rental. Ask about safety gear like lights and helmets, and perks like delivery to your accommodations.

Fall Fun in Florida

When you book a getaway with Rent the Keys, you won’t be short on fun fall activities to fill your time. From spending the day on the sand to spending the day lounging in your vacation rental, you’ll be able to build a getaway that is uniquely yours. Relax and unwind after a fun-filled day. Enjoy a one-bedroom for your small family or fall sweetheart getaway, all the way up to six bedrooms for a group reunion. Make a home-cooked meal in your unit’s fully equipped kitchen, many with stainless steel appliances. Enjoy the meal in the large living/dining areas, or in a private outdoor space. Relax in a private bedroom, or gather the family, pop some popcorn, and watch your favorite movie. Choose a premium unit for perks like a fireplace, double ovens, flat-screen TVs, a private pool, and more. Include the whole family by inquiring about select rentals that allow your fur babies to stay.

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Contact us today to book your fall fun Florida getaway!