Sign up for our emails to get exclusive news, information and the best rates on your vacation!
There’s something magical about a quiet Key West summer and fall. The island exhales. The streets are a little less busy. The breeze through the palms feels just a little sweeter. At Historic Key West Vacation Rentals, we believe travel should go (read)
Published on Aug 17, 2025
Key West is more than a sun-soaked destination — it’s a canvas. With pastel streets and colorful traditional homes, a rich literary legacy, and a long tradition of welcoming artists, the island pulses with creative inspiration. Whether you (read)
Published on Aug 08, 2025
At Historic Key West Vacation Rentals, we believe travel should be more than a getaway. It should be a connection — to a place, a past, and a way of life that invites you to stay a little longer, breathe a little deeper, and feel a little more like... (read)
Published on Aug 01, 2025
After the summer crush, many vacation destinations wind down in the fall, but Key West comes alive — with sunny skies, ocean breezes, and the perfect blend of relaxation and adventure for families. Planning a trip between September and (read)
Published on Jul 31, 2025
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... (read)
Published on Jul 06, 2025
The fall in Key West brings vibrant energy, cooler breezes, and the island’s most anticipated event — Fantasy Fest. From Oct. 17 to 26, 2025, the streets of Old Town will come alive with dazzling costumes, lively parades, and an infectious (read)
Published on Jul 03, 2025
Each year when the snow begins to fall and daylight disappears before dinner, there are those who wistfully dream of warm ocean breezes, sunshine and sand between their toes. But by then it’s really too late to do anything meaningful to change those (read)
Published on Jun 22, 2025
If you’re planning an August vacation to Key West, get ready to embrace the island’s easygoing spirit — because here, relaxation isn’t just an activity, it’s a way of life. And at Historic Key West Vacation Rentals (read)
Published on Jun 16, 2025
In Old Town Key West, where sun-faded porches meet storied streets, one cottage stands as a rare and powerful testament to the island’s layered past. Tucked near Bahama Village—a neighborhood shaped by the rich heritage of Bahamian settlers (read)
Published on Jun 09, 2025
Dreaming of sun, sand and sea this August? Look no further than fabulous Key West! The ultimate tropical getaway, Key West makes each day feel like a beach holiday — and at Historic Key West Vacation Rentals, we can chart your course with (read)
Published on Jun 04, 2025
Forgot password