Key West's Tranquil Autumn Vibes

key west autumn
by Historic Key West Vacation Rentals

It may stil feel like summer in Key West, but just know fall is here. Our Conch Republic has all things delightful and frightful for munchkins, monsters, pumpkin eaters and masqueraders alike. You can unlock the fall magic by being as adventurous as you like or kick back and relax in one of our luxury boutique vacation rentals, replete with Key West's tranquil autumn vibes.

Autumn in Key West

Visit before festival season starts when soaking up the autumn sun is as close to bliss as you can get.  Fall also signals the start of our stone crab claw season, so it's a great time to visit. Fantasy Fest is a 10-day party for grown-ups. Autumn is the best time to visit The Florida Keys if you are a Halloween junkie.


Fall Fun in Key West

Visit the animals at the Sheriff's Animal Farm Open House, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained.

The Key West Artisan Market includes a full bar and smoothies, juices, and coffee to wash down delicious food items you can eat immediately or take away. Shop for fine crafts, art, jewelry, and more.



November in Key West

Come November, Racing teams and fans are to gather in Key West for an amazing Offshore World Championship experience. RWO is the premier Offshore Racing Sanctioning body in the United States and is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event. Fan zone and entertainment at Truman Waterfront Park. Both general admission and VIP viewing options available.

The Key West Film Festival is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community. It strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. Named one of the “25 Coolest Film Festivals in the World” by Moviemaker Magazine.



Discover the Best Key West Vacation Rentals

With all this and more ushering in the season, you'll need an equally fall-tastic place to stay. Our collection of Key West Vacation Rentals includes nightly, weekly and Key West monthly rentals with plenty of cottages, condos, and larger houses to select from.


Key West Monthly Rentals


We invite you to stay 28 nights or longer to experience luxury accommodations like Azur Palm, Fish Camp and The Escape At Sunset Key. If you're traveling with friends or family, especially teens, you might opt for our newest monthly conch-style home with a guest cottage. It's called Sunshine and Shenanigans and it's located in a quiet, residential area, The Meadows.  Just a short bike ride will take you to many Key West attractions, shopping, and restaurants.

Unlocking Key West's fall magic starts with an online booking or a call to our magical team at 305.296.1010. Key West's tranquil autumn vibes are waiting. How soon can you get here?