Historic Old Town Oasis • Pool + Walk to Duval Street | Monkey House

*Please note that this home is available for 28+ night stays only.*

Monkey House is a one-of-a-kind Key West escape where playful design, tropical color, and a lush courtyard setting come together for a stay that feels full of personality. Tucked within the historic Midnight Cowboy compound, this two-bedroom retreat places you just two blocks from Duval Street while giving you a vibrant hideaway to return to between beach days, gallery strolls, and nights out.

Inside, the home is bright, eclectic, and full of character, with whimsical details, bold pops of turquoise, and an easy indoor-outdoor feel. The cozy living area and kitchen keep things simple and comfortable, while two king bedrooms and two bathrooms make the layout ideal for couples, friends, or a small family looking for a memorable Key West stay.

The outdoor space is the real showstopper. Step into a lush courtyard oasis with a lagoon-style pool, sunny loungers, colorful seating, and a waterfall feature that adds a playful, resort-like touch. Whether you’re cooling off after exploring, sipping drinks by the water, or relaxing under the palms, this shared pool area brings the best of island living right to your doorstep.

Monkey House also carries a unique artistic history. The compound was once connected to writer James Leo Herlihy, author of Midnight Cowboy, and welcomed a creative circle that included Tennessee Williams and other notable artists and writers. Today, that spirit continues through the home’s funky style, colorful details, and unmistakably creative atmosphere.

Best of all, you’re just moments from the heart of Key West. Walk to Duval Street for dining, drinks, music, galleries, and people-watching, then return to your tropical courtyard escape for a swim, a quiet evening, or one more nightcap under the palms. Monkey House is playful, historic, and unmistakably Key West — a stay made for guests who want their trip to feel as memorable as the island itself.

Monkey House is part of the Midnight Cowboy compound, which also includes the Main House (1 king bedroom) and Hibiscus Suite (studio-style space with a queen bed) at Tennessee Williams. Stay at Monkey House, or rent the entire Midnight Cowboy compound for a total of four bedrooms. Need even more room for your group? Just next door, the Boat House offers an additional king bedroom along with a living area, kitchen, and full bathroom. All spaces share access to the central pool area and outdoor washer/dryer.

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.
- If you require more space, this listing is also available as part of a buyout called Midnight Cowboy which has a total of 4 bedrooms.
- There is also another 1 bedroom listing located on the same compound called Boat House. Please reach out to the team to enquire about availability.
- 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.
- 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.
- Please note that max occupancy includes infants.
- Please be advised that documentation may be necessary for ESA/service animals to gain entry.

Parking Details:
Shared parking space. One parking spot for this unit.

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The room configuration is as follows:

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