Welcome to A Thousand Hidden Hemingways

The Ultimate Key West Luxury Vacation Rental.

The Perfect Location in Key West’s Old Town….

to launch your adventures, or to simply relax the day away. Key West was once the home to Ernest Hemingway, where he was inspired to write the majority of his novels.  Key West is filled with hidden creatives, geniuses, misfits and pirates- simply the most interesting people you’ll ever meet.   Yet, they’re hidden away behind lush tropical foliage, in 150 year old cottages, farmhouses and victorian mansions. 

Come wander the lanes of Key West and discover these 1000 Hidden Hemingways.  

Find paradise right outside your window as the sun rises on this sanctuary

Rooftop sun deck, Key West Florida
Front porch of our Florida Keys historic vacation rental home
Sunny kitchen looking out at the pool deck
Warm, cozy bedroom with AC

Experience the Florida Keys in a vacation home unlike any other…

The home was built in 1890's, with a farmhouse charm, and porches off of every bedroom.  It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces.  It's perfect for family gatherings, or just a quiet escape.  Each room is sunny and bright, with beautiful furnishings and every amenity you could want.  The bathrooms are conveniently located and can accommodate larger groups, and now have fabulous Japanese-style bidets.

The house AC throughout, WiFi, and TVs with Apple TV in every bedroom.

The gourmet kitchen is well equipped, and looks out (via large folding sliding glass doors) on a covered outdoor living space, with chaise and dining table.  The pool is just steps further, surrounded by lush tropical plants.  Sunbathing here or on the upper deck is a must.   In the evening, the large upper deck has string lights- a perfect environment for drinks, dessert, or conversation.

If you're looking for the real Key West experience, A Thousand Hidden Hemingways is the place.  And if you wander around our neighborhood, you just might find some more like minded folks...


Take a tour, from where you’re sitting right now.

Take a walk through the halls, kitchen and bedrooms to see the magic for yourself.

 

Amenities Perfected.

The Basics

  • Sleeps: 10

  • Bedrooms: 4

  • Beds: 3 King, 2 Twin, 2 rollaway twin

  • Bathrooms: 3

  • Minimum Stay: 28 nights

  • Living Area: 2200 sq. ft.

  • Large Heated Pool

  • On-site Parking

  • Car available for rent

Unique Benefits

A huge rooftop deck: over 400 sf, with shade umbrellas and multiple chaises. Every room in the house has access to a deck or porch, so you can always find a quiet corner to yourself.

Why Kids Love It

The pool, the ultimate family hangout! Discover the ideal oasis for families at our vacation rental. Immerse yourself in a vast covered outdoor living space, mere steps away from a sparkling pool. Here, children can frolic and play, while parents indulge in cooking, dining, and unwinding in total comfort.

Features

  • Air conditioning

  • Beach chairs

  • Bed linens provided

  • Private, heated pool

  • Heating

  • High-Speed Wireless Internet

  • Cable TV

  • Apple TV

  • Spacious, kitchen, fully equipped for gourmet cooking

  • Outdoor dining table

  • Poolside patio (covered) with sofa + chaises

  • Pets allowed

  • Sun Deck with umbrellas + chaises

  • Towels + Linen provided

  • Large capacity washer + dryer on site

 

Attractions Within Walking Distance

Aquarium • Beaches • Bicycling • Boating • Canoeing •  Deep Sea + flats Fishing • Golf • Grocery Store • Jet Skiing • Kayaking • Movie Theater • Park • Playground • Sailing • Scuba Diving • Shopping Area • Snorkeling • Tennis • Volleyball Court • Water Skiing • Pickleball Courts

Spacious rooms.

Unforgettable activities.

Your activity guide awaits.

We’ve put together a map of all our favorite things to do in key west!

Be fully in the moment,open yourself to the powerful energies dancing around you.
— Ernest Hemingway