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Key West, FL

Midnight Cowboy

Sparkling Clean
Check our enhanced cleaning and sanitation protocols. Show details
Work-Friendly Space
Laptop friendly with high-speed WiFi.
Tech-Enabled Locks
Check yourself in with the keypad.
Please note that this home is available for 28+ night stays only.

Midnight Cowboy is a one-of-a-kind Key West escape consisting of three beautiful spaces. The Main House boasts dual living areas, a fully equipped kitchen, and a king bedroom with an ensuite. Nearby, the Monkey House offers two more bedrooms (both kings), a cozy kitchen, and two bathrooms. The Hibiscus Suite houses a queen bed in a studio setup complete with a bathroom and kitchenette. All spaces share access to a lush central pool area with a large patio, tons of lounge space, and an outdoor washer/dryer. The entire Midnight Cowboy compound can be rented with Boat House, a charming 1BR home located just next door, which also has access to the pool.

Fifty years ago, James Leo Herlihy, the author of "Midnight Cowboy," was probably the second most renowned writer living in Key West, just a notch below his close friend and mentor, Tennessee Williams, who was a frequent visitor to 709 Bakers Lane along with luminaries such as Truman Capote, Richard Burton, Elizabeth Taylor, Tallulah Bankhead, Leonard Bernstein, Elizabeth Bishop, James Merrill, and Thomas McGuane. The artistic tradition continues today as the compound is owned by a family of funky writers and artists that have received many honors and awards, including a MacArthur Genius Award, Order of the British Empire, and a National Endowment for the Arts, among others.

No matter how your group chooses to spread out, this triple-space retreat will stun with its beautiful outdoor oasis and playful, eclectic design present within each home. Bright pops of color, unique furniture and decor, and an overall lively atmosphere can be found in every corner.

Outside, cool off in the pool, grab a lounger in the sun, or relax in the covered patio lounge. The pool even has a waterfall feature hiding a small grotto that kids and adults alike will love. A side courtyard gives you the perfect place to steal away for a quiet moment, while plenty of surrounding trees provide a great sense of privacy and seclusion. Bonus: you'll be within two blocks of the excitement of Duval Street, with shops, bars, restaurants, and art galleries all waiting to be explored!

Get ready for an exciting blend of artistry, amenities, design, and relaxation at Midnight Cowboy, your first choice for a Key West experience like no other!

Key West is a place unlike any other in the United States. Connect with marine life through diving or fishing, or sightseeing along the beautiful turquoise beaches. Nature is abundant, and so are the bars! Known for its nightlife, you will play as hard as you work in Key West, although it remains a wonderful destination for families and solo travelers alike. Make sure to chow down on some of the local seafood or Cuban-influenced cuisine---the country is only about 100 mi away.

Experience Key West, AvantStay style.

AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team and a tech-enabled concierge to book services, such as fridge stocking, mid-stay cleanings, and private chefs. For anything you need (or never knew you needed), we're at your service!

Local Attractions: Key West Shipwreck Treasure Museum, Hemingway Home and Museum, Mel Fisher Maritime Museum, Harry S. Truman Little White House, Conch Tour Train, Dry Tortugas National Park, Lazy Dog Adventures, Dolphin encounters, Ghosts & Gravestones Tour, Old Town Trolley, Sloppy Joe's Bar, Audubon House & Tropical Gardens, Florida Keys Eco-Discovery Center, Bike Tours, Seaplane adventures, Key West Aquarium, Sebago Day Tours, Private boat charters, Sportfishing, Rick's Entertainment Complex, Duval Street (shop strips, shops, bar, and cafes), Mallory Square (waterfront plaza), Key West Garden Club, Sunset Pier, Grand Cafe Key West, Island House, El Meson de Pepé, Cafe Sole

Home Truths:

Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.
Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.
This is a buyout of 3 listings located next to each other in the same compound.
If you require more space, there is another 1 bedroom listing located on the same compound called Boat House. Please reach out to the team to enquire about availability.
Please note that the laundry area is a shared space.
This home has access to a shared pool.
Please note that this home does not have central heating and air conditioning, but we do have mini split units in each room.
This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.
Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.
Please note that max occupancy includes infants.

Parking Details:

You'll have 2 parking spots.
No garage

What can I expect in the home?

  • Private Parking
  • TV
  • Patio
  • Washing Machine
  • Dryer
  • Wifi

Room details

Our home features 4 comfortable bedrooms for a perfect night's sleep.

Each room is outfitted with linens, towels, fluffy pillows and comforters. Linens are available for additional sleeping arrangements.

Sleeping arrangements

  • 3 xKing Bed
  • Queen Bed
Primary Bedroom (Main House)
2 guests
King Bed, TV, Ensuite
Primary Bedroom (Monkey House)
2 guests
King Bed, TV
Bedroom 2 (Monkey House)
2 guests
King Bed
Hibiscus Suite
2 guests
Queen Bed

House Rules

Special Restrictions

You must be at least 25 years old to book this property.

Humans Only

Pets are not permitted at this property. Unauthorized pets may be subject to a fine.

Thank You For Not Smoking

This is a smoke-free home. Violation of the no-smoking policy will result in a $500 fee for additional cleaning and other related costs, in addition to the Guest being responsible for any damages attributable to smoking beyond said fee.

Respect Community Rules

Please be considerate of your neighbors and mindful of noise levels. Noise violations may result in fines. Please also note we do not provide speakers or sound systems.

Cancellation & Refund

to view the cancellation policy.
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