These three neighboring Old Town cottages offer privacy, charm and space for group travel.
Managed by Historic Key West Vacation Rentals
Tucked along a private, gated walkway in Old Town, these neighboring Conch-style homes were originally built for artisan cigar factory workers during the island’s 19th-century cigar boom. Today, they’ve been beautifully restored to offer adults-only getaways that blend Key West’s storied past with modern comfort.
Breathe in the history and enjoy the best of Key West living at these nightly rentals:

Step through the tropical gardens to your secluded 2BR, 2BA hideaway.
With vaulted ceilings, French doors, and Dade County pine throughout,
the deluxe Hibiscus Cottage offers room to unwind — with a king
ensuite, a cozy open-loft bedroom, and a shared pool just steps away.

From the moment you step into Flamingo Cottage, you’re wrapped in
that signature Key West glow. Bright, colorful, and full of island charm,
this 2BR, 1BA cottage features warm Dade County pine, a skylit
open loft, and an inviting living area perfect for relaxing.

Blending historic character with modern comfort, Gardenia Cottage is a bright and inviting 2BR, 1BA hideaway designed for easy island living. It features hardwood floors, a sunny living room with a skylight, open-loft sleeping, and a king bedroom leading to a serene private patio

Each cottage shares access to a large
tropical pool, tucked at the back of the
property and surrounded by palms and
sunshine. It’s the perfect place to
lounge between island adventures.

With Duval Street, local restaurants,
and Key West’s famous nightlife just
a short stroll away, guests can enjoy
the ideal mix of walkable convenience
and tucked-away tranquility.
Booking cottages separately is a smart choice for friends or couples traveling together, offering privacy and flexibility without compromising connection. Spend the day exploring Key West as a group, then retreat to your own cozy corner for a good night’s rest.
After all, sharing a vacation doesn’t have to mean sharing every moment — and as we like to say, neutral corners can save friendships, too!
Whether you’re drawn to the vibrant energy of Duval Street or the quiet
beauty of Key West’s historic lanes, each cottage offers the perfect
home base. Make your next adults-only getaway one to remember
— together, or with just the right amount of space in between.
Book Your Stay Today
Our Guest Services team is here to help with everything from fishing charters to art stroll recommendations.
Call us at 305.296.1010 (Option 5)
Email: concierge@historickw.com
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Historic Key West Vacation Rentals 1119 White St Key West, FL 33040 USA