[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Midnight Cowboy by AvantStay | 3 Artistic Spaces Vacation home with kitchen, a short walk to Duval Street ![Pool](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634295/0ddf2496.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634295/e181615a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634295/24b27fad.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634295/61a1964e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634295/e1e4426b.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location In the heart of Key West, Midnight Cowboy offers a one-of-a-kind escape with three beautiful spaces. The Main House, Monkey House, and Hibiscus Suite share access to a lush central pool area with a large patio and tons of lounge space. 10 Exceptional ### Entire home 4 bedrooms4 bathroomsSleeps 82992 sq ft ## Popular amenities - Pool - Dryer - Parking available - Washer - Kitchen - Outdoor space ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### 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 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! 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 \--- 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 \--- 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. ## Property amenities ### Beach - Beach nearby ### Pool/Spa - Communal pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Kitchenette - Oven - Refrigerator - Stovetop ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 4 bathrooms - Hair dryer - Shower - Towels provided ### Entertainment - Smart TV ### Outdoor areas - Garden - Patio ### Laundry - Laundry facilities - Washing machine ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Concierge services - Iron/ironing board ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit - Fire extinguisher - Deadbolt lock ### General - Garden - Unit size: 2,992 square feet ## Similar properties ![Pool](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634299/2c46f525.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Monkey House by AvantStay | Pool, by Duval Street Old Town Key West - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=99634299&PinnedHotelID=99634299&HadPinnedHotel=true®ionId=-1&adults=2) ![Pool](https://images.trvl-media.com/lodging/100000000/99640000/99634300/99634297/36c232a1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Tennessee Williams by AvantStay | Funky Design + Pool Old Town Key West - Pool - Kitchen - Washer - Dryer 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=99634297&PinnedHotelID=99634297&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112300000/112293300/112293233/536ef4ae.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Rooster Doodle Do - Midtown Family Retreat New Town - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=112293233&PinnedHotelID=112293233&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/54000000/53950000/53949100/53949015/f5ad1c22.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom with Off Street Parking and Pool! 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Old Town Key West - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=112166091&PinnedHotelID=112166091&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110650000/110641100/110641080/f4db96ec.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Heron House | Canal Front 3-Bedroom Home w/ Private Boat Docking in Key Haven Key West - Kitchen - Washer - Dryer - Pet-friendly [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=110641080&PinnedHotelID=110641080&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as e1fba3d5-cce7-11ed-b7f8-f708980fb040 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.55623%2C-81.79896&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=5l10Np0UX-Eb940Nmk_qXSA9rSg=) Key West, FL #### What's nearby - Duval Street - 5 min walk - 0.4 km - Ernest Hemingway Home and Museum - 11 min walk - 0.9 km - Mallory Square - 13 min walk - 1.2 km - South Beach - 15 min walk - 1.3 km - Southernmost Point - 17 min walk - 1.5 km #### Getting around - Key West Intl. Airport (EYW) - 12 min drive #### Restaurants - ‪Willie T's - ‬6 min walk - ‪DJ's Clam Shack - ‬5 min walk - ‪Misohappy Sushi & Thai - ‬5 min walk - ‪The Cafe - ‬5 min walk - ‪Mangia Mangia - ‬5 min walk ## Frequently asked questions ### Does Midnight Cowboy by AvantStay | 3 Artistic Spaces have a pool? > Yes, this property has a pool. ### Is Midnight Cowboy by AvantStay | 3 Artistic Spaces pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Midnight Cowboy by AvantStay | 3 Artistic Spaces? > Check-in begins at 4:00 PM. ### What time is check-out at Midnight Cowboy by AvantStay | 3 Artistic Spaces? > Check-out is at 10:00 AM. ### Where is Midnight Cowboy by AvantStay | 3 Artistic Spaces located? > Located in Old Town Key West, this vacation home is within a 10-minute walk of The Kite House, Duval Street, and Ernest Hemingway Home and Museum. South Beach and Mallory Square are also within 1 mi (2 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Midnight Cowboy by AvantStay | 3 Artistic Spaces Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 1 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Cleanliness ### 10/10 Excellent #### Kat M. Aug 5, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Unique as Key West This collection of homes is truly a unique stay. From the decorations to the location to the wonderful large pool, it is a stay to be remembered. We stayed for a month and found the property management company extremely available and engaged. We had some concerns upon arrival and all were addressed immediately and with flare. I will certainly be considering re-renting this property in the future! Thank you! ##### Kat M. 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