6 More Reasons To Spend October In Key West

the pool at reel paradise vacation rental

Those who've enjoyed fall getaways to Key West know what we're talking about.  If you've ever considered an autumn adjournment to our Caribbean paradise, there's plenty to of reasons to make it so. While folks in other parts of the country are pulling out their flannels, corduroy and wool socks, those of us in the Conch republic are putting on more sunscreen, refilling our cocktails and saluting more of the most beautiful sunsets in the world. To add to the allure, there are some of our most fun and enjoyable events lined up for October. Let's take a look at several and some of our luxury boutique cottages and homes at ready to welcome you.

SCARECROWS IN THE FOREST   Date: September 15, 2021 - November 30, 2021

The Key West Tropical Forest & Botanical Garden’s second annual Scarecrows in the Forest event features locally designed scarecrows from individuals, creative professionals, organizations and businesses. Scarecrow creators use natural and recycled materials. 

Where To Stay: Inn Cogneato Cottage - Monthly Rental 2 Bedrooms 2 Baths 5 Guests     

MARKET ON THE GREEN   Date: October 2, 2021

Admission is free. Come shop amazing local artisans, including but not limited to: Pera Collection, Authentic High Country Hemp, Key West Island Art, Kaley Bentz Art, Sea Gypsy 33, Key West Spice, Copper Esposito Designs, Made by Soto, Anna’s EsSCENTials Bodycare, Irish Red Photography, Boxes by Frank, Washed Ashore, Louis Zaslow Art and Annes Artsy Antic. 

Where To Stay: Chavez House - Nightly Rental 3 Bedrooms 2 Baths 6 Guests

SOUTHERNMOST MARATHON   Date: October 7, 2021 - October 9, 2021

Imagine running through the southernmost island in the United States while enjoying a break from the ordinary.  The Southernmost Marathon & Half / Key West Running Festival promises just that- 26.2, 13.1 or 3.1 miles of ocean and gulf views, as well as iconic Key West landmarks. Join us this fall for Key West and the Florida Keys premier race- the Southernmost Marathon & Half. Come for the race and stay for a good time! All participants will receive an event t-shirt at packet pick up and finisher medal.

Where To Stay: Reel Paradise - NEW Monthly Rental2 Bedrooms 2.5 Baths 5 Guests        

SMALLEST PARADE IN THE UNIVERSE   Date: October 7, 2021 - October 28, 2021

Pint-sized float entries with this year’s Fantasy Fest theme: All-A Daze for a Holiday.

Where To Stay: Starfish - Monthly Rental2 Bedrooms 2 Baths 4 Guests   

FANTASY FEST   Date: October 20, 2021 - October 31, 2021

During the festival, visit our new Fantasy Zone Festival Hubs, for awesome Photo Ops and up-to-the-minute festival information. Purchase your must-have fest T-shirts, hats and koozies, and meet our local festival concierges, who can help you plan your schedule for the week or just find the best late night eats or live music. You can also score some samples and swag from our festival sponsors.

Where To Stay: The Pink House - Monthly Rental 2 Bedrooms 2.5 Baths 5 Guests 

38TH ANNUAL HEADRESS BALL Date: October 28, 2021

The Key West Business Guild presents the 38th annual Headdress Ball on Thursday, February 20th, 2021 at 8 pm.  Gates Open 6:30 pm. Show begins 8 pm. Coffee Butler Amphitheater. 

Where To Stay: My Happy Place - Monthly Rental2 Bedrooms 2 Baths 4 Guests  

These are six more reasons to spend October in Key West.  We're even offering fabulous last-minute rates on our available rentals. Reserve yours right on our website or with our very fall-friendly vacation planners. Come on down and fall in love with Key West and Historic Key West Vacation Rentals.