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

Anna Maria Island Historical Museum

Take some time out of your busy schedule of fall activities in the Florida Keys to learn about where you’ve chosen to stay. The Anna Maria Island Historical Museum 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 evidence of Native American cultures in 700 AD.


An island 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 – like take a walk, sit and soak up the sun and read, or watch the kids build sand castles. Whether you choose one of our rentals on the mainland or surround yourself with water, the many area beaches are a top priority for any family getaway. The best part?

Browse Our Florida Keys Beachfront Homes Here!

Anna Maria Island Bayfest

The event is back for its 20th anniversary. Visitors and islanders alike come together at the event for food, fun, arts and crafts, a car show, live music all day long and more. The one-day event is October 16, 2021, from 10 a.m.-9 p.m. Admission is free, and transportation to the Pine Avenue location is free on the Anna Maria Trolley.

Other Festivals and Fairs

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


For the golfers in the group that want to golf near the Gulf, there are two Longboat Key courses you won’t want to miss. Both courses call the Resort at Longboat Key Club home. Links on Longboat is a par 71, 18-hole course full of small waterways running along one side of the fairway on many holes. Check the course website for tips on the “Signature holes” and how to play them. The Harbourside course is located three miles north of the Links on Longboat and is made up of three nine-hole courses so you can mix and match nines for your own unique 18-hole challenge. The “White Egret” nine features tight fairways, while you may drown your ball at any moment on the “Red Hawk.” You’ll have a taste of everything – including ample wind as well as nine of the 45 total “signature holes” of the club’s holes.

Bicycle Rentals

Like on many islands, there are several places that a motor vehicle can’t go. Gather the group and explore the many walking and bike trails that let you see the sights of the Florida Keys during fall that aren’t accessible by car. You will find a bike to fit the needs of each family member. You can rent single-seat bikes with or without gears (also known as 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.

Family Fun in Florida

When you and the family book a getaway with Rent the Keys, you won’t be short on fun, family-friendly activities to fill your time. From spending the day at the sand to spending the day lounging in your vacation rental, you’ll be able to build a family getaway that is uniquely yours. Relax and unwind in a private vacation rental after a fun-filled day. Enjoy a one-bedroom for your small family, all the way up to six bedrooms for a family reunion. We have single-family homes for extra privacy. For even more privacy and peace of mind, book a rental with a private garage. Make a family meal in your unit’s fully equipped kitchen, many with stainless steel appliances. Enjoy the meal in the large living/dining areas in many rentals, or in a private outdoor space. At the end of the day, relax in a private bedroom, or gather the family, pop some popcorn, and watch your favorite family movie. Choose a premium unit for perks like a fireplace, double ovens, flat screen TVs, private pool – some are even screened in for added protection from the hot Florida sun. Include the whole family by inquiring about select rentals that allow your fur babies to stay.

Contact us today to book your family fun Florida getaway!

Check Out Our Airbnb Rentals in Cape Coral!