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  • (305) 294-7358
Key West Time
May 28th
10:33am · 87°F

Little Digs Key West ~ Monthly Rental

1BR 1BA ~ Monthly Rental
Sleeps 2

Diminutive in size but huge in style, ‘Little Digs Key West,’ authenticates how ‘big things’ really do happen in small spaces.  Key West was centuries ahead of its time in the modern day ‘tiny house movement.’ Long before small living spaces became a fashionable environmental trend, living on a little 2 x 4-mile island launched a progressive movement to recraft classic Key West cottages into luxurious little dwellings.

With a gabled tin roof and board and batten window shutters, the curbside presence of this circa 1933 Key West rental cottage is charming as can be. It sits in proud harmony with other historic  cottages, on a narrow one-way lane, smack dab in the center of Old Town Key West. In 2010, a progressive designer / builder was inspired by its presence and completely transformed the interior to a luxury standard, not often bestowed on a 500 SQ FT abode.


Living / Dining Space: The interior of Little Digs Key West rental was redesigned as three spacious rooms. The main room is the open concept living room / kitchen. Soaring ceilings that are tucked up to the roof line create an uplifting feel. Soft white walls and sash windows along the front and side stream in the sunlight. Dramatic recessed ceiling lighting, hardwood flooring, and soft blue sheer curtains unify the space.

Décor throughout the cottage embodies casual modern tropical elegance. Living room walls are painted a creamy white, enhancing a calming tone. Furnishings are set for comfort and versatility. The living room grouping, staged to one side of the room, is done in relaxed linen, beach wicker, and dark wood. For entertainment, a large flat screen TV is mounted on the opposite wall. For dining and working remotely, a wooden drop leaf table and two chairs are set against the front wall.

Kitchen: Two soft glowing pendant lights placed above the breakfast counter, visually divide the kitchen from the living room. The custom designed U-Shape kitchen is built-out with nutmeg tone wood cabinets, a deep porcelain sink, shiny black granite counter tops, and a brown and white mosaic tile backsplash that pulls it all together. High-end stainless-steel appliances and a gas stove make the kitchen a pleasure to cook in. Two bar stools are thoughtfully placed at the breakfast counter for sitting during meal prep and having a snack.

Bedroom: Across the room from the breakfast counter, is bedroom. Surprisingly spacious, the bedroom it is serenely decorated with a beach inspired theme. Sea-life artwork bring an island vibe into the space. A mother and baby mermaid painting, by our favorite Caribbean artist David Wegman, is featured above the bed. The bedroom is painted in a soothing sand tone and decorated with blue and white fabrics and white wicker furniture. The bureau is placed on the wall opposite the bed, where a flat screen TV is set for easy viewing. The closet offers plenty of space to hang clothes and stow belongings above. Three sash windows along the front and side walls, bring in plenty of natural light.

Bathroom: The bathroom is conveniently located just outside the bedroom door at the back of the cottage. An oversized shower with black granite walls tiled to the ceiling, a tumbled marble tile floor, and frameless glass doors create a luxurious ambiance. A frosted transom window on the exterior shower wall brings in the natural light. Walls are painted the same soothing sand tone as the bedroom. A free-standing porcelain sink is topped with an elegant mirror and vanity lighting. An over-the-toilet cabinet bathroom cabinet provides storage for bathroom essentials.

Bedding Summary:

• 1 Queen Size bed

• 1 Queen Size sleeper sofa


Front Porch- For sitting outdoors, the front porch is set with two chairs, a corner table and privacy curtains. This is a great place to sit and sip a cup of coffee or glass of wine while enjoying a charming view of Windsor Lane. Writers and locals are your neighbors on this famous historic lane, and people watching is always interesting. While there is no yard with the cottage, there is plenty of green space to enjoy just a minute walk away in two different directions.

Nearby Green Spaces - It’s easy to get outside and relax in a green space from this cottage. Many Key West residents live in small homes with no yards and enjoy their outdoor time in pocket parks. The neighborhood pocket park near Little Digs Key West, is little known William Butler Park. This is a minute walk away down a tiny lane intersecting lane.  A cool Caribbean setting, it has playground equipment and plenty of space to sit under the shade trees and take in the island ambience.

The other green space is the Key West Cemetery, just a  one-minute walk down Windsor Lane. Established in 1849, it’s a huge landmark 19-acre space, filled with fascinating grave markers that give a glimpse into the intriguing history of Key West. Filled with gorgeous tropical trees, it’s a favorite place for both locals and visitors to walk and bicycle through.

Amenities: Beautifully furnished island modern style with nice artwork. Central A/C, flat screen TV’s in the living room and bedroom, Wi-Fi, fully equipped upscale kitchen, upscale bathroom, linens and towels provided. Washer / dryer inside yard laundry closet.

Parking: There is no off-street parking. You can generally find a parking place on one of the lanes close by. This neighborhood was built before there were any cars on the island. Walk everywhere from this location. We can help you arrange to park and leave your car in the covered  Old Town Parking Garage.

Area: Situated in the wonderful location of Solares Hill, the cottage is on Windsor Lane, at the highest point of the island – at a whopping 18 Feet. Locals snidely joke about ‘getting nose-bleed up this high.’ This is a fabulous neighborhood to wander in. A hand full of side streets intersect with little lanes with names like Love Lane, Nassau Lane, Poorhouse Lane, and Catholic Lane - each a reflection of a more innocent yesteryear. Streets and lanes are lined with wooden cottages and Victorian homes built by early ship builders and island settlers.

Activities: Besides the little-known William Butler Pocket Park in one direction, and the famous Key West Cemetery in the other, from here you can walk to downtown shopping in 5 minutes. Easy stroll to art galleries, internationally famous fine restaurants, sailing, boating, diving, museums, nightlife, Mallory Square. Simonton Beach is an easy walk away. Be sure to check out Little Pearl, an acclaimed neighborhood restaurant only two blocks away, and The Funky Rooster Coffeehouse and Wine Bar, just a few blocks in the opposite direction.

Restrictions: Smoke free house. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.


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special rates available


May 30- June 30

Monthly $4,100

view all specials

Dates Monthly
May 1, 2024 - May 31, 2024 $4250
Jun 1, 2024 - Jun 30, 2024 $4250
Jul 1, 2024 - Jul 31, 2024 $4250
Aug 1, 2024 - Aug 31, 2024 $3750
Sep 1, 2024 - Sep 30, 2024 $3750
Oct 1, 2024 - Oct 31, 2024 $4250
Nov 1, 2024 - Nov 30, 2024 $4250
Dec 1, 2024 - Dec 31, 2024 $4600
Jan 1, 2025 - Jan 31, 2025 $6000
Feb 1, 2025 - Feb 28, 2025 $6000
Mar 1, 2025 - Mar 31, 2025 $6000
Apr 1, 2025 - Apr 30, 2025 $4775
May 1, 2025 - May 31, 2025 $4250
Jun 1, 2025 - Jun 30, 2025 $4250
Jul 1, 2025 - Jul 31, 2025 $4250
Aug 1, 2025 - Aug 31, 2025 $3750
Sep 1, 2025 - Sep 30, 2025 $3750
Oct 1, 2025 - Oct 31, 2025 $4250
Nov 1, 2025 - Nov 30, 2025 $4250
Dec 1, 2025 - Dec 31, 2025 $4600

Additional Notes:

  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter.
  • Future Dates not listed, please call 305-294-7358 for pricing.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

Bedding Summary:

• 1 Queen Size bed

• 1 Queen Size sleeper sofa

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