photos by Barry Fitzgerald and VHKW
If only this old house could talk, as they say, what stories it could tell. Wonderfully off-beat, a little bit funky and Bohemian by design this old house on tiny Ann Street is authentic to the bone. Over the years it’s been a Key West Address * for some notoriously colorful characters. Some say it has some local ‘claim to fame,’ and all would agree it has interesting legend and plenty of tasty trivia. What’s in the name? Inspired by the James T. Slater’s song with the same name, we think it helps describe why we love this house so much.
It first took its place in Key West in 1938, about the time the infamous marriage of Ernest to Pauline Hemingway was waning, along with The Great Depression. As the story goes, the gregarious Papa was traveling back and forth between Key West and Spain, reporting on the Spanish Civil War, while fueling his love for Martha Hadley. When Pauline finally had enough she moved out. This Key West address was new on the block, and this is where she landed.
Over the decades, the immediate area around Ann Street area evolved into a prominent downtown bohemian neighborhood for artists, writers, hippies, and adventurers. In the 1970’s, another gregarious character, Ashley Simmons, aka the “Woman going crazy on Caroline Street,” took up residence in this house and was immortalized in the song by Jimmy Buffet. Then in the 1980’s, colorful artist the late Captain Outrageous moved in here and set up his art gallery right next door on the corner of Caroline Street. If you’ve been to Key West before, you’ve probably seen his at least a piece of his art in the street memorialized on cars, scooters, or bicycles.
Although the property is right downtown Key West, around the corner from main Key West features like Mallory Square and Sloppy Joe’s Bar, this house manages to be off most people’s radars. Maybe because it’s low-key presence blends so naturally into the scenery of the neighborhood. Or maybe it’s because ‘it’s been here forever.’ Either way, all this means for you is that this house is sort of an ‘insider’s secret.’
The Bohemian Design:
This two-story house has retained most of its original character by design. While over the years it has been updated with essential creature comforts, it has been deliberately kept with an undeniable Key West bohemian flare. The concept was to retain the quirky quaintness of the house, not to ‘over-renovate’ it, to celebrate its colorful past by filling it with stylistic shabby-chic and comfy furnishings, and original local art … like we used to do in the 1970’s. The result is A Key West Address vacation rental that’s as genuine as they come.
With that as our goal, in the most recent update, we paid steadfast homage to it’s endearing past by engaging the talents of international artist, Capt. David Wegman who has art studios in Key West and St. Barth’s, Virgin Islands. Best known for his Caribbean style folk-art, we commissioned him to create two artistic focal points in the house by painting two original wall murals. Downstairs, in the kitchen, he created an interpretation of a vintage Cuban Menu Board from the 1930’s we found in the Key West library. The other mural, at the top of the stairs leading to the master bedroom, he painted a blue-gray sepia tone beach scene reminiscent of a Caribbean post card from the same era.
Original architectural features have been preserved, and most rooms in the house have historic features including clear heart-pine floors and walls from floor to ceiling, and wooden doors with decorative gingerbread molding. Downstairs ceilings in the living room and kitchen, and the upstairs master bedroom and bathroom are nearly 14 feet high. Antique French doors in the living room have wood panels on the bottom and stain-glass windows on the top.
We painted the walls throughout the house in muted tones of Caribbean blue, sand tone, pale lavender, and sage green, and decorated them with an eclectic collection of art including many original pieces by Captain David Wegman. For furnishings, we went for a bohemian ‘shabby-chic’ style combining antiques with comfortable modern chairs and sleeper sofa.
Interior Layout (Downstairs):
The front entrance to the house steps directly into a short hall that leads to the living room. Your eyes will immediately be drawn to the living room where a giant oversized mirror captures your reflection as you enter the house. A beautiful antique French door is set to separate the living room from the entrance hall, but there is really no need to close it. It’s more for style and ambience.
The two downstairs bedrooms are located on either side of the hall. Referring to our slide-show of this house, as you enter the house, the bedroom to your right is the pale blue bedroom and light wicker headboard. The bedroom to your left is the khaki colored room with the painting of the beach shack above the bed and the chocolate colored wicker headboard.
The downstairs bedrooms are very cozy (some say tiny), but please don’t take this wrong. Even though they are small and intimate, there is plenty of light from double sets of sash wood frame windows. Each downstairs bedroom has loads of original style and décor, and each provides a comfortable pillow-top queen-sized bed. Both bedrooms have been thoughtfully decorated with reading lamps on both sides of the beds, hanging closets, ceiling fans, hardwood floors, and original art. We maximized the bed size in both of these bedrooms and set them with pretty linens. When you walk you, you’re enticed to jump right into bed.
Straight ahead into the spacious living room, which spans about two-thirds of the width of the house, we find a stylish space set for comfort. The high ceiling makes the space feel larger than it is. On one side of the living room, a grouping has been set with a pale blue sleeper sofa, a striped slipper chair, and a white antique wing-back chair. A 1970’s style bamboo entertainment center was chosen to hold the large flat screen TV and DVD player. At the other end of the room, a pub-style dining table and chairs have been set in one corner, complimented by an antique sideboard the owner brought from Argentina.
Directly past the dining area is the ‘spick n span’ butler style kitchen. The focal point of the kitchen is the large “Cuban Menu” mural painted by Capt. David Wegman. There’s some hidden humor here at the last gold starred menu item and we invite you to find it. The kitchen has been repainted and scrubbed to the bone, but the original layout has been left intact for the most part by the choice of the owner to retain the Bohemian feel. Hand-made solid wood cabinets go all the way to the ceiling, and the original deep porcelain kitchen sink and the blue tile counters are an endearing hold-over from the Captain Outrageous days. It does give a very authentic 1970’s feel, which I personally love.
Off the kitchen is the charming downstairs bathroom. A re-fresh of this room gave it a new bathtub in November 2011, and some new fixtures, but the original corner style porcelain sink and hardwood floors have been left in place. Lots of artistic touches in this bathroom will make you smile and think of the ‘Old Days’ in Key West.
Interior Layout (Upstairs):
The upstairs of the house can be accessed from two points: through interior French doors off the back of the living room; or from the exterior back door entrance. Either way, the original wooden staircase that goes straight up to a landing on the 2nd floor. The staircase is worth mentioning as it is rare to find this old-style of basic stairway still in tact in Key West. While there is nothing fancy about it, its hand-hewed quality lends it nostalgic charm. To enhance natural artistic quality of the stairs, we painted the risers white and the treads a chocolate brown, and had David Wegman paint the large blue-gray sepia tone mural at the top of the stairs that is described earlier.
The Caribbean mural lures you up the stairs, where to the right, is the entrance to the master suite. This could be considered the most enviable room of the whole house. Aside from being the former abode of several noteworthy Key West characters, it reminds me of an exotic bedroom in an old Bahamian manor I once stayed in.
The entire upstairs has very high ceilings and all rooms are built floor-to-ceiling of original heart pine wood. The first room at the top of the stairs is the very cool bathroom which was renovated to add a large walk-in shower and a vintage style free-standing sink. A six foot sash-window with antique lace curtains invites in sunlight that is bounced around by multiple mirrors. Neat little nooks and crannies, give a vintage feel to the bathroom. Directly past the bathroom is the doorway leading to the walk-in closet and beautiful spacious master bedroom.
Furnished with Colonial-Caribbean style mahogany furniture, the bedroom offers a four-poster king sized bed, a large dresser, TV armoire, and side table. Reading lights are placed on either side of the bed. Walls in the master bedroom are painted light lavender to contrast the mahogany furniture and an antique red striped satin chair is placed in one corner. This room is also filled with sunlight by 4 double sets of six foot sash-windows, on three of the bedroom walls. At the opposite end of the room from the entrance, original narrow-style French doors lead to a balcony off the bedroom with plenty of room to sit and lounge in privacy.
Grounds: The house is discretely set back from the street so that it’s easy to miss it when you walk by. The first thing you notice from the street is the vintage Spanish style concrete garden wall topped with original wrought iron fencing. Entrance to the property is gained through a wrought iron pedestrian gate or the gate to the carport to the left of the house. Once inside the gate an old brick patio leads to a short set of stairs and up to a wooden deck.
Wood decking, elevated about four feet from the ground, is used to cover most of the yard starting in the front and wrapping around the left side of the house to the back. The back deck provides some seating space, but the front deck gets the sun and is set up as the main lounging area. It has large sunken in-deck Jacuzzi tucked off to the left as you face the house, and a full-size patio dining table with umbrella on the right. The front and side of the property is landscaped with mature tropical trees to create some privacy from the street.
*Note: What’s in the name? Inspired by the James T. Slater’s song, Key West Address, we think it captures the spirit of this house and help express why we love this house so much. Check out the YouTube video. It even has cameo shots of David Wegman. (He’s the dude with the long white beard.)
1st Floor – 2 Queen size beds; 1 Queen Sleeper (in the living room)
2nd Floor - 1 King size bed
Amenities: Private Jacuzzi, decked yard, equipped kitchen, cable TV, C/D player and stereo. Linens and towels are provided. There is no washer / dryer at this property but pick-up laundry service is available and can be arranged for you. Off-street parking for one COMPACT car only in carport. Best to use the carport to park rented bicycles or mopeds. From this location you don’t need a car.
Activities: One block from lower Duval in the 200 block means you are off-the beaten path in a residential street, but just around the corner from Sloppy Joes Bar on block, and the Bull & Whistle Bar on the other. Don’t worry about noise – people comment on how quiet this street is for as close as it is to the action. Close to famous Key West Historic Seaport, short walk down the street to Mallory Square Sunset Celebration. There are too many great restaurants bars and eateries within close walking distance to mention them all. You’re also right around the corner from the Mel Fisher Treasure Museum and the Custom House Museum. Stroll to theaters, shopping, water sports and beaches.
Area: One block off lower Duval Street in the 200 block in downtown Old Town where Key West was founded. You’re as close as you can get to Front Street and stay in a private authentic vacation rental. Here you are just steps from Green Street which is part of the Key West Harbor Walk that goes from Mallory Square to Schooner Wharf. Walk to all Old Town features.
Restrictions: Smoke free house. This property is best for adults, but well behaved children are okay. We do not accept guests less than 25 years of age unless accompanied by an older adults or guardian. Smoking permitted outside only. Absolutely no pets. (Please don't ask!)