Historic Key West Vacation Rentals

This summer, step outside the ordinary. Butterfly Cottage invites you to slow down and settle into the relaxed rhythm of Key West living. With 2BR, 2BA, a welcoming butterfly front porch, and a private back deck, this beautifully renovated cottage is ideal for couples or small families looking to escape everyday life. June, July & August availability. https://www.historickeywestvacationrentals.com/vacation-rentals/butterfly-cottage

In the vibrant Historic Old Town of Bahama Village, where the legacy of 1800s Bahamian settlers meets modern possibility, a brighter future unfolds. With the Southernmost Point, Duval Street, and eclectic spots like Bésame Mucho, Blue Heaven, Santiago’s, and La Crêperie just a step away, Inn Cogneato-Monthly Rental is poised to become the foundation of your next great chapter! https://www.historickeywestvacationrentals.com/vacation-rentals/inn-cogneato-cottage

With a nickname like the Conch Republic, it should come as no surprise that Key West is a seafood-mad town. At the Art Deco Eaton Street Seafood Market and Restaurant, you can try conch in fritters, chowder, and even ceviche, while B.O.’s Fish Wagon turns out crispy cracked conch “seawiches.” But it’s far from the only signature seafood in these parts: Other standouts include lobster-like royal red shrimp, which are in season from late summer through late fall, and Florida stone crab claws, best enjoyed cold with mustard dipping sauce at the Half Shell Raw Bar or the A&B Lobster House.

For something a touch more sophisticated, Old Town’s Little Pearl is a neighborhood wine bar where the chef’s tasting menu might include pink shrimp and waffles or grouper cheek bao buns.

8 cool coastal towns for seafood fans - Tripadvisor ‘Tis the season for chowder, lobster rolls, and so much more.

Let the sun, sea, and spirit of Key West bring your family together. Book a month-long stay this November with Historic Key West Vacation Rentals and enjoy the perfect mix of home comforts, historic charm, and tropical beauty, all designed to help you focus on what matters most. Ready to plan your Thanksgiving escape? Explore our collection of unique historic homes and book your fall or early winter stay today! See you this November in fabulous Key West! https://www.historickeywestvacationrentals.com/blog/november-in-key-west-gobble-up-the-ultimate-holiday-upgrade

Step into the vibrant spirit of Gardenia Cottage, where the rich history of artisanal craftsmanship meets the excitement of possibility. With Duval Street's eclectic energy just a stroll away, and a refreshing shared pool to revive you, every day is a chance to create unforgettable memories.
https://www.historickeywestvacationrentals.com/vacation-rentals/gardenia-cottagenew-nightly-rental

Founded in 1832, St. Paul's Episcopal Church is the oldest US congregation south of St. Augustine. Located at the bustling corner of Duval and Eaton Streets in Key West, Florida, the church features stunning stained-glass windows, offers open sanctuary space, and hosts daily organ recitals.

Florida Keys & Key West is turning up the heat with a summer of local traditions, world-class culinary festivals and landmark America250 celebrations.

Memorial Day weekend kicked off with the 36th Annual Schooner Wharf Minimal Regatta along with the Murph Challenge at Big Pine Key Memorial Park. The rest of the summer months through Labor Day weekend offer more exciting local-inspired events.
https://www.travelpulse.com/news/destinations/what-s-happening-from-key-largo-to-key-west-in-summer-2026

Imagine waking up in a space that embodies the essence of possibility! This beautifully reimagined 'eyebrow' house in Key West is more than just a rental - it's a catalyst for transformation, where luxurious design and airy California vibes come together to inspire a brighter, more vibrant you. Reserve it now for your June, July, & November vacations! https://www.historickeywestvacationrentals.com/vacation-rentals/california-dreaming

As you enter this carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool awaits you. Later, you can cozy up to a bedroom of your choice. Tropical Dream-Monthly Rental is available for your June and September vacations! https://www.historickeywestvacationrentals.com/vacation-rentals/tropical-dream