Fall in love with paradise: Why the off-season could be the best season in Key West
When most travelers think of a Florida getaway, they picture the high-energy winter season or spring break crowds. But savvy vacationers know that the best time to visit Key West just might be during the fall. As summer melts into a quieter, cooler season, the island transforms into a tranquil paradise where the pace is slower, the experiences are richer, and the hospitality is as warm as the sun.
At Historic Key West Vacation Rentals, fall is our best-kept secret — and here’s why the off-season is the perfect time to plan your tropical escape:
The perks of Key West in the fall
- Fewer crowds, more paradise: Fall in Key West means you can enjoy everything the island offers — without the long lines or packed attractions. Visit popular spots such as the Hemingway Home, Fort Zachary Taylor Beach, or the Southernmost Point without the hustle. Dining at local restaurants is more relaxed, with better availability and personalized service.
- Ideal weather: October and November bring balmy breezes, cooler temperatures, and lower humidity. You can explore the island by bike, lounge poolside, or enjoy a sunset sail without the intensity of summer heat or the chill of winter. It’s the perfect blend of sunshine and comfort.
- Incredible events: Fall in Key West isn’t sleepy — it’s spirited. Fantasy Fest takes over Old Town each October with a vibrant week of costumes, parades, and revelry. Other autumn events, including island-wide art and food festivals, keep the calendar exciting.
- Better value on vacation homes: One of the best parts of a fall visit? Off-season pricing. You’ll find more availability and competitive rates on our stunning collection of vacation homes, all while enjoying the same luxurious amenities and unbeatable locations. It’s a smart traveler’s dream come true.
Stay historic, stay local
Historic Key West Vacation Rentals offers a curated collection of beautifully restored homes that let you live like a local in paradise. Whether you’re here for a long weekend or an extended month-long stay, we have the perfect home base for your fall escape.
Here are a few guest-favorite properties for a cozy fall retreat:

- Sunny Daze Cottage: This monthly rental is perfect for guests seeking a peaceful escape. With bright interiors, modern amenities, and a prime Old Town location, you’ll feel instantly at home at this 2BR, 2BA beauty.

- The Escape at Sunset Key: Want the ultimate fall fantasy? This luxurious, 2BR/3BA monthly rental on the exclusive Sunset Key island offers unmatched privacy and views — just a short ferry ride from downtown.

- Chavez House: This nightly rental blends historic architecture with modern flair, offering 3 BRs and a front-row seat to all the island action.
Getting here is easier than ever
Key West International Airport offers direct flights from cities such as Atlanta, Charlotte, Chicago and Dallas, making your fall getaway just a few hours away. Skip the stress and step into island time quickly and conveniently.
Fall is waiting
Autumn in Key West is a magical time filled with gentle breezes, colorful sunsets, and the laid-back charm that makes this island famous. Whether you’re coming to unplug, explore, or celebrate, you’ll find the perfect place to stay with Historic Key West Vacation Rentals.
Published on Sunday, July 6, 2025