The warmth and sun of Florida are a major attraction any time of year. Lounging in the sun or splashing around in the water of the Gulf of Mexico is a fun and relaxing way to while away the time on a Florida getaway, but you’ll want to make sure to experience some of the Halloween fun and excitement available for both kids and adults when you plan a fall break around one of the spookiest days of the year. Here’s what to expect when you enjoy Spooky Siesta Key.

Siesta Key Safe Treats

Trick or Treating on Siesta Key is safe and fun, thanks to the Siesta Key Chamber of Commerce.  The 38th annual Safe Treats for Kids is an event where merchants across the island will be handing out sweets and treats to costumed children. The afternoon event is a fun, relaxed event and the free Siesta Key Breeze Trolley can help you get between Siesta Key Village and Turtle Beach so you can maximize your fun. The free event is Monday, October 31 from 3-6 p.m. at participating businesses across the island.

Sarasota Dog-A-Ween Costume Contest

Kids and adults alike dress in their Halloween best for costume contests every Halloween. When you bring your pup with you on your Siesta Key Halloween adventure, make sure he or she gets to sport their best Halloween look, too. Head over to Sarasota and Paul Thorpe Park and let your pooch strut in their Halloween best. The 14th annual event takes place on October 29 at the Sarasota Farmers Market Halloween Festival. Check-in is from 9-9:45 a.m. at Lemon Avenue & 1st Street in Downtown Sarasota, and a parade starts at 10 a.m. from the check-in point to Paul Thorpe Park, where the contest will be held at 10:15 a.m. Registration is $15 by October 27. Dogs must be leashed on a non-retractable leash at all times. has a link to registration.

Haunted Sarasota Tour

Dolley the Trolley departs from Trolley Cottage Tiki Bar and embarks on a tour of ghoulish proportions. Mummies, Mayhem, & Murder includes a 90-minute narrated tour about famous murders, haunted buildings, and unsolved crimes. The fully enclosed and air-conditioned trolley is piloted by a Ghost Hostess, and you may pick up surprise guests along the way. Costumes are encouraged, and the tour includes complimentary beer or wine from the bar before departure, as well as free parking. Guests must be at least 12 years old, and 21+ to drink alcohol. Please no audio or film recording during the trip.

Boo! At the Bay

The after-dark, “not-so-scary” evening includes trick-or-treating, pumpkin picking, yard games, food trucks, prizes, and much more! Wear your spooky – or not-so-spooky – costumes. The free event takes place at the Bay Park – Civic Green at 655 North Tamiami Trail in Sarasota and is part of the “10 Days at the Bay” series running October 14-23. Boo! At the Bay takes place on October 21. Special activities include a sensory-friendly experience from 5-6 p.m., the “Spooky Moonlight in the Mangroves Tour” from 6:30-8 p.m., and Family Movie Night (“Hocus Pocus”) from 7:30-9:30 p.m. All special events require advanced registration, available through their website,

Other Activities

Don’t forget you came to Siesta Key to rest and relax in the Florida island sun in addition to some great Halloween attractions. There are plenty of indoor and outdoor activities that don’t necessarily have a spooky theme. Gather your loved ones and head to the beach for swimming, stand-up paddle boarding, sandcastle building, and much more. Head to some of the indoor attractions like escape rooms, museums, galleries, restaurants, shopping, and an endless amount of other activities. You can also choose to decorate your rental with removable, non-damaging decorations or create a Halloween-themed scavenger hunt or other activity that keeps you closer to home and away from the larger crowds of community events.

Halloween on Siesta Key

When you book a spooktacular Halloween getaway to Siesta Key with Rent Siesta Key, you won’t be hard-pressed to find something to fill every minute of every day of your trip. Fuel up for the day or bring everyone together with a delicious home-cooked meal or Halloween treat prepared in your unit’s fully equipped kitchen. When the spooky fun is done for the day, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show. When you’re not at the beach or soaking up the Halloween fun, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat-screen TVs, and more. We have a rental to fit your needs, from one-bedroom units for your small family or a spookily romantic getaway all the way up to six bedrooms for a Halloween reunion with friends or family.

Contact us today to book your Halloween getaway and make memories to last a lifetime!