Midnight Cowboy by AvantStay | 3 Artistic Spaces

★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays.

*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!

AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!

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.

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.
- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.
- This home has access to a shared pool.
- Please note that the laundry area is a shared space.
- 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.
- Please be advised that documentation may be necessary for ESA/service animals to gain entry.

Parking Details:
- You'll have 2 parking spots.
- No garage

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The room configuration is as follows:

Main House:
King bed w/ ensuite

Monkey House:
Bedroom 1 / King bed
Bedroom 2 / King bed

Hibiscus Suite / Queen bed

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This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking.

We report and prosecute all Credit Card Fraud.