Welcome to a vacationer’s contemporary conch house with 2-bedrooms, 2-baths, and a secluded pool and deck oasis. Room by room the residence reflects its past and its present. This vacation home located in the Key West Historic District with its intricate, hand carved wooden trim and abundance of Dade County Pine (both hallmarks of classic Key West architecture) reflects the past as recognized by its listing on the National Register of Historic Places. Inside, this home has been updated so that its historic roots blend seamlessly with modern amenities to meet the needs of today’s savvy vacationer while offering easy access to everything Key West has to offer.
Behind a white picket fence and up a few stairs is the front porch that runs the width of the house. Comfy chairs and a double swing make a great place for coffee or cocktails on the quiet lane, while green palms and bright yellow hibiscus add color and tranquility to the scene. A tall metal chicken with crazy eyes stands guard by the wooden screen door. Once inside and to the left is the living room with hard wood floors, Dade County Pine walls, and a decorative ceiling fan above. The ceiling itself is a light wood that bounces light from the four louvered windows back into the room to create an airy feeling. End tables with lamps, a handsome couch with pullout bed, cushioned armchairs, and an ottoman that can also function as a coffee table make this the right spot for conversation. Across the room is a cabinet and a large flat screen TV perfectly positioned for viewing from the couch. And of course there’s A/C, high speed internet, and cable.
The downstairs bedroom features a queen bed with ensuite bath. A dresser, chairs, bookcase, and corner desk area make this a relaxing space for the quieter pursuits like reading and sleeping. A ceiling fan with light above and louvered windows guarantee plenty of daytime light in the room or closed for quiet solitude at night. The ensuite bath enhances convenience and privacy. Its emerald glass vessel sink is a one-of-a-kind statement piece and the visual centerpiece of the room while a closet for fluffy towels and other amenities provide convenience and space for storage.
The U-shaped kitchen follows with a striking glass ceiling light shade made by local Key West artisans, illustrating colorful forms of sea life like fish, turtles, shells, and coral. The second striking aspect is the large pass-through window to the pool oasis beyond. The kitchen itself offers a modern blend of expected appliances and accoutrements for preparing food in a comfortable and attractive layout. Multiple white cupboards above and below store dishes and more for the convenience of cooking in for a break from Key West social life, with a small table and three chairs that can function as a mini breakfast nook just steps from the covered lanai.
Upstairs the open master suite spans the second floor. A full-length window lights the length, with side windows adding a treehouse feel to the room. There is a large desk for computer work or play, an upholstered chaise lounge for stretching out and reading, and a wonderfully comfortable king bed with an intricate filigree headboard beautifully backlit by a window behind. Upstairs also includes a generous closet complex for hanging clothes, for folded accessories, and for the washer/dryer. In the shower, an oblong porthole window provides function and interest, with a view of the bougainvillea over the patio. (Note the shower opens into the room (see pic.)) The adjoining private bath area includes a toilet with bidet, sink cabinet, another set of shelves, and a counter for storage and workspace for daily wash-up activities.
Back downstairs is what many name the most compelling aspect of this amazing cottage: the covered lanai; the deck; the heated, saltwater pool; the small, covered patio; the back-lit tropical landscaping. The covered lanai is serviced from the large and handsome pass-thru window connecting food and drink from the kitchen ever so easily to the outside table and chairs. A TV, carved ceiling fan, small refrigerator, and decorative flourishes make the area irresistible. Not to mention the view of the pool/deck oasis. On one side is a row of colorful Adirondack chairs and on the other a deep blue tile back drop with water feature. In between is a magical saltwater pool that could easily be where you spend most of your home time swimming or floating. Above is an incredible Key West sky with puffy white clouds and an occasional water bird flying over. The whole back area is ringed in a white fence and palms that create beauty and privacy. Behind the gleaming tile wall is a small, covered pavilion to park a golf cart, scooters, or bikes (access is through a lane at the rear of the property but it is too small of an egress/ingress for anything larger than a golf cart – NO cars, etc.) or as an extended social area or work area or most anything you want. A grill area and hammock invite you to savor lazy afternoons or festive gatherings. There is no car/truck parking on this lane nor the one behind the home. The closest on-street car parking is on the main side streets - White and/or Frances.
This homeowner has exterior surveillance equipment. Historic Hideaways is not in the care, custody, or control of their placement, use, or what they may or may not record.
The Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. If this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We do not guarantee that the information VRBO (and affiliated sites) obtains from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
A Latitude Adjustment at the Truman Annex in Key West
Truman Annex
A Latitude Adjustment at the Truman Annex in Key West
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Key West
Located near the beach, this holiday home is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Sails To Rails Museum at Flagler Station and The Kite House are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
Ernest Hemingway Home and Museum - 5 min drive - 2.4 km
Getting around
Key West, FL (EYW-Key West Intl.) - 12 min drive
Restaurants
Cuban Coffee Queen Waterfront - 7 min walk
Schooner Wharf Bar - 10 min walk
Kermit's Key West Key Lime Shoppe - 11 min walk
Half Shell Raw Bar - 8 min walk
Pepe's Cafe - 7 min walk
Frequently asked questions
Does Pineapple Conch House - 2 BR Old Town Pool Home have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Pineapple Conch House - 2 BR Old Town Pool Home?
As of 25 Apr 2026, prices found for a 1-night stay for 2 adults at Pineapple Conch House - 2 BR Old Town Pool Home on 1 May 2026 start from AU$257, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Pineapple Conch House - 2 BR Old Town Pool Home pet-friendly?
No, pets are not allowed at this property.
How much is parking at Pineapple Conch House - 2 BR Old Town Pool Home?
This property doesn't offer parking.
What time is check-in at Pineapple Conch House - 2 BR Old Town Pool Home?
Check-in begins at 4:00 PM.
What time is check-out at Pineapple Conch House - 2 BR Old Town Pool Home?
Checkout is at 11:00 AM.
Where is Pineapple Conch House - 2 BR Old Town Pool Home located?
Located in Key West Historic District, this holiday home is within a 15-minute walk of Key West Burlesque Theater and Duval Street. Florida Keys Beaches and Mallory Square are also within 1 mile (2 km).