The warmer climates of Florida and its many beaches are a great place to getaway any time of year. When fall cools temperatures in many other parts of the country, Florida’s welcoming warmer temperatures have tourists flocking to the area for a fall break. Add some island sand and sun and you’ll be marking days off the calendar to your arrival. Make your fall getaway extra special this year by adding some spooky Halloween in the Florida Keys fun to the agenda. There are plenty of family friendly options as well as scares for teens and adults only.

Fright Night on St. Armand’s

If you want to be at the main attraction on Anna Maria Island this Halloween, head to St. Armand’s Circle on October 31. The young and young at heart are invited to an evening of fun and fright. Storefronts will be decked out in their Halloween best, and you’ll want to watch out for spooky monsters and spirits on every corner. Bring the kids in their costumes for a fun evening of trick-or-treating throughout the Circle.

Trail of Treats

Anna Maria Island is the place to be this Halloween. Kids ages 0-12 can show up in their costumes and trick-or-treat safely on the Trail of Treats. There is a costume contest starting at 3:30 at the Anna Maria Island Chamber of Commerce and the trick-or-treating is from 4-8 p.m.

Farmer’s Market

Fall means harvest time, and harvest time means farmer’s markets. Check local schedules when you arrive and make time to attend a market and score fresh produce, homemade crafts, décor, and more to brighten up your Halloween in the Florida Keys getaway.

Bradenton Beach Ghost Tours

While not specifically a Halloween in the Florida Keys attraction, the Bradenton Beach Ghost Tours celebrate the island’s spooky past, including shipwrecks and ghost stories based on eyewitness accounts. The 90-minute tour starts at 8 p.m. on Bridge Street Tuesdays-Saturdays. Advanced tickets are required at a cost of $10-15.

Fruitville Grove Pumpkin Festival

You’ll have to head to the mainland and Sarasota for this one. This year’s 33rd annual festival runs weekends throughout the month of October and ends on October 31. Where a suitable costume and come for food trucks, live music, the Kids Fun Zone, pony rides, or attend the craft show. You can hold a big or skunk, walk the Wildflower Maze, go to the petting zoo, or have an Enchanted Unicorn Encounter. Take a horse drawn carriage ride and enjoy the many other activities available. There’s a free children’s costume contest every Saturday at 2 p.m. See the Torres Family Circus and the Globe of Death with Extreme Riders for free on weekends at 11:30 a.m. and 3:30 p.m. The fun ends with a bang on October 31 with trick or treat at the festival vendor booths from 12-5 p.m. Most events are free, but some range from $1-10 for supplies. Parking is $5. The farm market and pumpkin patch is open during the week 9 a.m. – 6 p.m. for shopping fall décor, fresh produce – including the pumpkin for your Jack-O-Lantern – and fall photos at the pumpkin patch.

Pumpkin Festival

For the last 28 years, Anna Maria Island has celebrated fall and Halloween with their annual pumpkin festival. This year’s festival brings hayrides, a petting zoo, corn maze, rock climbing, a barnyard playground, craft show and many other activities. There will also be live entertainment each weekend, from musical guests to stunt shows to dog shows. Admission is $10 for guests ages ten and up and includes admission to many venues. Events and activities with extra fees include face painting, pony rides, and train rides. Entertainment differs from day to day, so you’ll want to check the calendar and plan which days to attend. The festival runs the weekends of October 12 & 13, 19 & 20, and 26 & 27 from 9 a.m. – 5 p.m. at Hunsader Farms in Bradenton.

Halloween in the Florida Keys

Make your next Florida Keys getaway full of water, sand, sun, and fright when you visit this Halloween. While you’re scheduling all the fun activities and attractions you’ll visit, don’t forget to book a vacation rental with Rent the Keys. Choose a one-bedroom unit for your small family or frightful sweetheart getaway, all the way up to a six-bedroom for a Halloween haunt for your larger family or group. Cook up a favorite Halloween treat or meal in the fully equipped kitchen. Gather together in the open living area and tell ghost stories or watch a scary movie. Enjoy private outdoor spaces like patios, decks, or balconies. Close your eyes and take a nap or get a good night’s sleep before more spooky fun in a private bedroom. Choose a premium unit for upgrades like stainless steel appliances, wood floors, and more.

Contact us today to book your Florida Keys getaway this Halloween!