The year-round sun and warmth of Florida makes it the ideal destination any time of year. Pack your bags and gather your loved ones for a fun and exciting Thanksgiving in the Florida Keys vacation full of fun, sand, and sun. 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.

Thanksgiving Dinner

Many restaurants on Anna Maria and in the surrounding area are providing residents and guests alike with traditional Thanksgiving fare. If you’re looking for an island meal, Anna Maria Island Beach Cafe or Waterfront Pier 22 have delicious offerings, and Marina Jack in Sarasota serves mouth-watering Thanksgiving meals, along with their regular offerings.

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Turkey Trot

Work up an appetite for your Thanksgiving in the Florida Keys meal and join in the annual Thanksgiving Day Turkey Trot. The fun run on the beach of Lido Key is full of exercise, entertainment, food, and fun. The event starts at 8:00 a.m. at the Lido Beach Pavilion. Kids ages 6-17 can get their exercise for a $25 sign-up fee, and adults age 18+ can stretch their legs for $40. All proceeds benefit ALSO Youth’s programs services to support LGBTQ+ youth.

Anna Maria Island Historical Museum

Take some time out of your busy island Thanksgiving schedule of activities 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 long history. Visit the old city jail, now a popular Anna Maria tourist spot but previously the actual city jail that was in use until the 1940s. You can also 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 on the island 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 on the beach, sit and soak up the sun and read, or watch the kids build sand castles. Rest and relax and let dinner digest as you soak up the sun on Bradenton Beach, Anna Maria’s main beach, or any other piece of sand you can find. 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 getaway.

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Bicycle Rentals

Like on many islands, there are several places that a motor vehicle can’t go on the Keys. Gather the group this Thanksgiving and explore the many walking and bike trails that let you see the sights of the Florida Keys during the Thanksgiving holiday that aren’t accessible by car. At most rental agencies, you will find a bike to fit the needs of each group 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 or adult bikes with baby seats. Many rental companies also provide complimentary locks and baskets with your rental. Make sure to ask about safety gear like lights and helmets, and perks like delivery to your accommodations.

Light Up Siesta Key

Celebrate the coming of the Christmas season on Siesta Key. The island’s annual Light Up Siesta Key & Village Holiday Parade celebrates its 36th year on Saturday, November 27, 2021. The Village Holiday Parade begins at Avenida del Mare and Beach Road at 5:30 p.m., Santa will be at the Siesta Center from 6:30-8:30, and the shops and restaurants will be offering refreshments and special holiday pricing. The free festivities run from 5-9 p.m.

Thanksgiving Fun in the Keys

When you book a Thanksgiving getaway with Rent the Keys, you won’t be short on fun Thanksgiving activities to fill your time. From spending the day at the sand to spending the day lounging in your vacation rental after a delicious meal, 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 Thanksgiving family or group 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 Thanksgiving meal in the large living/dining areas in many rentals, or al fresco in a private outdoor space. Relax in a private bedroom, or gather your group, pop some popcorn, and watch your favorite 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 Florida sun. Include the whole family by inquiring about select rentals that allow your pet to stay.

Contact us today to book your Thanksgiving in the Florida Keys getaway!

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