A Key West Address - Wonderfully Off-Beat Old Town House
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- Minimum stay:Contact manager
- Pets considered:No
- Wheel chair accessible:No
Private Homes, DownTown villa description
If only this old house could talk, as they say, what stories it could tell. Wonderfully off-beat, 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.
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.
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.
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.
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. 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. Most ceilings in the house are nearly 14 feet high.
Interior Layout (Downstairs):
The front entrance to the house steps directly into a short hall that leads to the living room. A beautiful antique French door is set to separate the living room from the entrance hall. The two downstairs bedrooms are located on either side of the hall.
These bedrooms are very cozy but even though they are intimate, there is plenty of light and each bedroom has loads of original style and décor, and each provides a comfortable pillow-top queen-sized 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. 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.
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.
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.
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. 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.
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 It reminds me of an exotic bedroom in an old Bahamian manor I once stayed in.
The first room at the top of the stairs is the bathroom which was renovated to add a large walk-in shower and a vintage style free-standing sink. A six foot sash-window invites in sunlight that is bounced around by multiple mirrors. 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. 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. At the opposite end of the room from the entrance, original French doors lead to a balcony off the bedroom.
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.
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 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.
• 1st Floor – 2 Queen size beds; 1 Queen Sleeper (in the living room)
• 2nd Floor - 1 King size bed
Keywords: Key West rental, Key West house rental, Key West vacation rental, Old Town Key West rental
- Vacation Rental
- Pets Not Allowed
- Minimum Age Limit For Renters
- Non Smoking Only
Bedrooms: 3 Bedrooms, Sleeps 8, Beds for 6-8
- King size beds (1), Queen size Beds (1), Sleep Sofa or Futons (1)
Bathrooms: 2 Bathrooms
Kitchen & Dining
- Catering Available
- Cooking Utensils
- Parking Off Street
- Air Conditioning
- Linens Provided
- Satellite / Cable
- Broadband Access
Pool & Spa
- Hot Tub
- Deck / Patio
- Outdoor Grill
- Jet Skiing
- Health/Beauty Spa
- Live Theater
- Wildlife Viewing
- Sight Seeing
- 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. ...moreless
ReviewsWrite a review
Location, location, location
Location, location, location
This property is adorable, quirky, & best of all right where you wanna be in Key West! It's VERY close to Duval st. & all it's nightlife, as well as many restaurants & shops; yet it's secluded enough away to get away from the commotion when it's time to head home. Property had 1 small parking space, which is a HUGE plus since parking in Key West is always hard to come by. We enjoyed our stay very much.
- Guest al (melbourne, fl )
- Date of stay 05/06/12
- Review Submitted 07/03/12
Recommended for: Sightseeing, tourists without a car, girls getaway, romantic getaway.
Winter: Dec. 15th - Apr 30th .. $3000/week ..$525/ night - Generally requires 7 night minimum Shoulder: May 1st to Aug 15th & Dec. 1st to Dec. 14th .. $2700/week .. $465./night 3 night min. stay available on reservations made within 60 days of arrival Summer: Aug 15th - Dec 1st .. $2500/week .. $425/night - 3 night min. stay available anytime. Holiday, Festival, & Event rates are 20% to 25% higher than published rates.
Note: Until confirmed, rates are subject to change without notice.
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Great room looking from living room to dining area and kitchen
Dining table set in corner conveniently off the kitchen
Kitchen looking at David Wegman art mural.
Master bedroom on 2nd floor look towards private balcony.
Large walk-in closet and dressing room in master bedroom
Downstairs bedroom #1 has a queen size bed.
Downstairs bathroom has a bathtub.
Front of the house. Note the off-street parking for one small car or bikes.
Great room looking from kitchen past dining room to living room area.
Looking into living room from stairway entrance hall.
Stairs leading to the master bedroom with en-suite bathroom.
Master bedroom standing at balcony looking toward door leading to en-suite bath.
Master bathroom upstairs on 2nd floor.
Downstairs bedroom #2 has a queen size bed.
Deck with in-deck Jacuzzi is private for the house.
Sloppy Joe's Bar, a Key West legend, is down the street and around the corner.
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This listing was first published here in 2012.
Date last modified - Saturday, November 23, 2013