In many parts of the world, Halloween is technically the first stage of winter, with trick-or-treaters having to wear coats and mittens over their costumes they so carefully planned, but in the Florida Keys, Halloween is more like the 3rd stage of summer, presenting with a lot less rain. Temperatures stay in the 80s, the water is still warm, and our white sand beaches, although not crowded, still offer a host of families all happily living the summer life as they build sandcastles, swim, and just relax in the warmth of the October sun. If your journey brings you here over a Halloween in the Florida Keys, however, and your children are looking in askance at your thought processes that could cause them to miss out on trick-or-treating, this Halloween guide to the Florida Keys will reassure them that no sacrifices will be made, especially when you come home every night to the seasonal comforts found in our RentTheKeys holiday hideaways.
Halloween in the Florida Keys is a Holiday Wonderland
As you know, we are located all over the Keys, so the prime activities events and activities are listed below according to location.
Trail of Treats on Anna Maria Island, Halloween, AMI Chamber of Commerce
Costume contests and trick or treating help make the holiday fun for costumed marauders of all ages at the Trail of Treats, a free event on AMI.
Hunsader Farms Pumpkin Festival, Weekends in October, 5500 C.R. 675 in Bradenton
Trick-or-treating in the neighborhoods of Bradenton will be fun, but this family friendly festival just may trump the begging. Offering pony rides, train rides, arts, crafts, live entertainment, hayrides, a petting zoo—ok, this list is endless, but we think you get the message. The Hunsader Farms Pumpkin Festival is a whole lot of FUN!
Trunk or Treat in Cape Coral, Friday Before Halloween, Cape Coral City Hall
Trunk or treating is always a fun way to get your candy and this fantastic event in Cape Coral offers games, music, and candy for all your costumed adventurers.
Halloween Notte in Port Charlotte, October 15-October 31, Charlotte County Fairgrounds
This next event is more for the older children in your traveling party, and that includes moms and dads! Offering three haunted houses guaranteed to make you scream, younger kids may be traumatized but we think your older tweens and teens will love this event, perhaps more than you do!
Siesta Key Safe Treats, Halloween, Ocean Boulevard in Downtown Siesta Key
Offering another opportunity to safely trick-or-treat, this fun and free event is sponsored by the shops of Siesta Key, with each shop that participates marking their door with holiday balloons. Parents can do a little window shopping and kids can dress up in their costumes and safely beg for candy, making it a win-win situation for everyone.
Halloween in Sarasota
The smaller towns and Keys offer a little less when it comes to Halloween activities, but Sarasota, which is within driving distance of all the towns we provide properties in, will more than meet your desire to celebrate this spooky holiday this Florida Keys Halloween.
Sarasota’s Halloween Pub Crawl, Joe’s on Main, Saturday before Halloween
Adults will enjoy a different kind of treat when they participate in this annual event, Sarasota’s Halloween Pub Crawl, sponsored by Joe’s on Main. Offering costume contests, Social Media Showdowns, Digital Photo Frames, and alcohol, this fun 21 and over event will be something you don’t remember if you do it right.
Sarasota Dog-O-Ween Contest, Downtown Sarasota, Saturday Before Halloween
It’s a dog, dog, world and the Sarasota Dog-O-Ween Contest, featuring costumed pets, raises funds for a local pet sanctuary. Every dog is invited to dress up in a costume and parade around downtown, so if you are staying in one of our pet friendly retreats, feel free to dress up your favorite fur baby and let him join in the fun.
Nathan Benderson Park Trick or Treat on the Lake, 5:30 PM
The dates vary on this annual event, it fell on a Tuesday in 2024, but the fun never lessens with this awesome trick or treat spectacular. Offering a candy trail of booths decorated to be spooky but not terrifying, there will be games, interactive activities, storytelling, live music, and a Halloween movie playing on the big screen. Also not terrifying ensuring that children of all ages will love this event! Admittance is free, but parking costs $10 per car.
Halloween in Our RentTheKeys Hideaways
The fun continues at home with RentTheKeys as you decorate pumpkins, binge-watch horror movies, and sneak a few pieces of candy from your children’s goody bags after they have slipped into their sugar rush comas. Remembering that chocolate pairs with red wine and fruit candies pair best with whites is our second favorite tip of the season. Reminding you to reserve your favorite holiday haven today is our absolute favorite, of course!
