Settle In. Slow Down. Live The Story.

Ten Thoughtful Reasons To Stay A Month With Historic Key West Vacation Rentals:

1. A HOME WITH A PAST – Sleep in a 19th-century cottage where the craftsmanship still shows — its old bones telling a story.
2. SPACE TO BREATHE – More time means less rush. Unpack, settle in, and let the island unfold naturally.
3. EXCEPTIONAL VALUE – Many of our homes offer a full month for the cost of just two weeks elsewhere. No hidden resort fees. Just value — and service with heart.
4. REAL WORK-LIFE BALANCE – Wi-Fi that works. Nooks that inspire. And the freedom to leave your watch at home.
5. A WALKABLE, HISTORIC NEIGHBORHOOD – Old Town’s tree-lined streets, cigar-maker homes, and hidden gardens become your new daily backdrop.

Why A Month?

Because something special happens when you stay long enough to know your neighbor's name, your favorite cafe's morning rhythm, and the exact time the light hits your porch just right.

6. LOCALLY MANAGED AND DEEPLY INVESTED – We’re not a listing site. We’re your hosts, your neighbors, your storytellers. We care how your stay feels to you.

7. PET-FRIENDLY, PEOPLE-WELCOMING – Many of our homes welcome pets — because a home wouldn’t be the same without every single family member.

8. LIVE THE RHYTHM OF THE ISLAND – When you stay longer, you stop chasing moments. You start living them. And spontaneity becomes your guide.

10. CAREFULLY CHOSEN COMFORT – Thoughtful touches, from crisp linens and comfy seats on shady patios, make every stay feel effortless

Why With Us?

Because our homes are more than rentals. They are lovingly preserved pieces of Key West history — each with its own personality and its own story to tell. The 10th reason to stay a month: 

10. A STORY YOU’LL NEVER FORGET – Whether it’s a birthday, a well-earned sabbatical, or just time for a change, this isn’t a vacation — it’s a new chapter.

Stay for a month. Embrace the calm. And reconnect — with yourself, with history, with something real.

Let us help you find the right home. We’re here for the moments that matter.