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  • (305) 294-7358
Key West Time
June 16th
4:50am · 84°F

On Hemingway's Rounds ~ Monthly Rental

2BR 2BA ~ Monthly Rental
Sleeps 4

Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful 2BR 2BA upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s established daily trail from home-to-bar-and-back-again, Ernest Hemingway undoubtedly passed by this house countless times. Here’s why …

On Hemingway’s Rounds monthly rental is on Whitehead Street - a short stroll from the Ernest Hemingway Home to the original Sloppy Joe’s Bar. Hemingway lived in his now museum home, at 907 Whitehead St., with his 2nd wife Pauline, from 1928 - 1938. Starting at dawn each day, he diligently wrote at his old wooden desk, which is now on display as a museum piece. But it wasn’t all mental discipline for Papa when he lived on the island. By 3:30 pm each day, he left his writing for the bar on Greene Street for his daily dose of cocktails, carousing and debating with friends - ostensibly gaining insight into island life for his next masterpiece. As Hemingway once said, “If you want to know about a culture, spend a night in its bars.”(Philip Green, Penguin Publishing Group, New York, To Have and Have Another, 2015.)

In the late 1920’s, Whitehead Street was still being built-out, green spots and vacant lots dotted along the road making it a quiet island stroll. As it turns out, this bungalow we call On Hemingway’s Rounds, was originally built before 1928, when Hemingway and Pauline moved into their home less than a block away. Since this house is less than a block away, and in a straight-shot path to the old Sloppy Joe’s Bar, this house was on his daily rounds.

An American Bungalow Gets a Re-Design:

This stylish vintage house, On Hemingway’s Rounds, is listed on the Key West National Register of Historic Places, as being originally built sometime between 1914 - 1926. Today it stands as an inspired renovation of a classic ‘American Bungalow’ redone Key West style. Perfectly redesigned inside, from top-to-bottom, to offer upscale fixtures and amenities plus luxurious outdoor living. Staying with historic guidelines, the street side and front porch remain true to the original casual craftsman form. But the interior now boasts an elegant simplicity and artful décor that meets even the most discerning of contemporary tastes. The result is a new design that includes upscale amenities inside and a spacious minimalist outdoor poolside scene in the back.


We begin our tour at the front of the house from Whitehead Street. It’s situated in a perfect little urban row of charming late 1920’s and 1930’s island bungalows. The picturesque curb appeal is both welcoming and somehow reassuring that life was and still is good. A short white picket fence anchored on an art deco concrete wall, makes the entrance to the tropical front garden. The wide front porch, with concrete columns with capital posts is genuinely charming. Furnished as a sitting room with a contemporary loveseat on one side and two matching chairs on the other, this is your perfect place to watch the world of Key West go by.  The porch sits just enough back off the street that you can sit and observe this main street in the downtown Old Town Key West neighborhood in privacy. 

Tropical landscaping and a paver-path wrap around the house to the completely fenced back of the property. Here we discover a minimalist garden paradise with a large wood composite deck, swimming pool, and select tropical plantings. Tanning chaises on the sun deck, plus a dining table and seating under an expansive covered deck, create a fabulous contemporary outdoor lounge. Grab the paper or a copy of ‘Old Man in the Sea,’ and some coffee and you just might end up staying here the entire morning.

Interior Layout:

Every room is very nicely laid out with unique and comfortable furnishings, and imaginative island-theme artwork. Multiple windows and sliding glass doors invite in the sunlight. Recessed lighting in tall ceilings and designer pendant lights over the breakfast bar, bounce around the light at night. A harmonious blue and white color pallet is used throughout the home for furnishings, wall paint and artwork. A combination of distressed and finished wood furnishings are blended with wicker and natural seagrass textural pieces to create a natural and sophisticated island ambience.

Great Room: Renovated to create an open-concept lifestyle, the spacious great room runs from the front door to the back of the house. The floor plan is staged with the living room at the front of the house. A corner furniture grouping features a coastal denim sofa and matching love seat, plus a wainscoting coffee table, large enough to put together a puzzle or play a board game. A 55” flat-screen TV is mounted on the wall opposite to sofa for easy viewing.

The kitchen encompasses the entire back of the great room. A double-level breakfast bar, towards the middle of the room creates a spatial division between the dining and living room areas, making it easy to serve snacks and drinks. Everything sparkles from top-to-bottom - from the bright-white cabinets to the white marble counter tops, to the stainless-steel appliances. For a sit-down meal, there is a round French bistro wicker and rattan dining table with a glass tabletop and four matching dining chairs. A laundry and housekeeping closet, with a stackable washer and dryer, are conveniently hidden next to the refrigerator.

Bedrooms and Bathrooms:

On Hemingway’s Rounds, provides two bedrooms and two bathrooms. A split-floor design offers maximum privacy, with one bedroom at the front of the house, and the other at the back of the house.

Front Bedroom: Standing at the front entrance of the house, the first door on the right leads to the front bedroom. This bedroom features a whimsical color-washed furniture ensemble. An extra-tall whitewashed wooden headboard is paired with a contrasting blue and whitewashed dresser. Matching swing arm lamps hung for reading on either side of the queen size bed, add an elegant touch. Beach theme artwork creates a cozy Caribbean ambience. A 50” flat screen TV is hung on the wall opposite the bed for easy viewing.

Double pane windows on the exterior wall bring in plenty of natural daylight. On the opposite wall, a door connects to a fanciful yet elegant en-suite bathroom. Whimsy is carried into the bathroom with a brightly colored sea-theme handmade pottery sink. In a softening contrast, remaining fixtures are shades of white on white. A round vanity mirror with an abalone shell frame adds a stunning touch. An elegant double size shower is finished with white faux marble tile and a pane glass shower curtain. For convenience, this bathroom also has a 2nd door connecting with the front of the great room.

Master Bedroom: Continuing to the back of the house, the last door on the right leads to the master bedroom. The décor is imaginative, handsome, and delightfully Hemingwayesque in style. A unique feature here is the exterior wall - the owners decided to preserve the original wood installed when the house was built using scrap wood and signs (look for the sign with date 1908) ! A king size bed with handwoven seagrass headboard is flanked by rustic wooden bedside tables with wrought iron handles. White ceramic reading lamps are placed as an elegant contrast to the rustic wood. A gorgeous Atlantic blue marlin is prominently displayed over the headboard. Opposite the bed, a dark-wood bureau is reminiscent of an antique writer’s credenza. A 50” flat screen TV is mounted on the wall above the bureau.

The master en-suite bathroom is elegant and refined in contrast to the rustic bedroom touches. A white marble vanity with brushed chrome fixtures tops the undermounted white porcelain sink. A round vanity mirror with a brushed chrome frame and arch vanity light are exquisite set against the blue painted wall. The double size shower is finished with a white faux marble tile and a pane glass shower curtain – same as the front bathroom.   

But the premium feature of the master suite is its seamless flow to the back deck and swimming pool garden. This visually brings the outdoors inside and keeps the view of the pool garden at eye level even when you’re relaxing in bed.

Bedding Summary:

  • Front Bedroom – Queen size bed
  • Master Bedroom – King size bed

Amenities: Private swimming pool. Completely fenced in minimalist style tropical garden. Large composite poolside deck with chaises for sunning plus a roof covered porch with dining table and easy chair seating. Front covered sitting porch with upscale outdoor furnishings. Fully equipped kitchen, central a/c, flat screen TVs in living room and each bedroom, washer / dryer, BBQ grill on the back deck. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.

Activities: There are an amazing number of things to see and do in this little Key West urban neighborhood. Less than a block away are the Ernest Hemingway House and Museum, Key West Lighthouse, and a plethora of famous Duval Street bars and restaurants. It’s close to Mallory Square Sunset Celebration, Bahama Village, and beaches and the Southernmost Point of the United States are a short walk away. Short walk to the Historic Seaport for sailing, boating, diving, and more restaurants, bars, and night life.

 Area: Whitehead Street is the island urban heart of  Key West, where we find many famous Key West museums and landmarks are located, including the Ernest Hemingway Home Museum, the Key West Light House, the historic Key West Courthouse, and the ‘End of the Road’ photo opt at Mile Marker Zero at U.S. Highway 1, and the offices of VHKW – Vacation Homes of Key West. This tiny section of Key West has many blocks of beautiful historic houses and bungalows. The original Key West City infrastructure was built in the 1800’s to create a diverse array of homes, shopping, entertainment, offices, restaurants, and churches. The 800 block of Duval Street is right around the corner. The Truman Annex entrance to Fort Zachary Taylor State Park and Beach is a 15 minute walk away.

Notes: This property is offered as a monthly or seasonal rental for persons who want to settle into the neighborhood for a month or more. This property is staged for professionals and executives who have discerning tastes looking for an upscale accommodation downtown Key West that provides luxury home amenities.

Parking: Parking for this property is on the street. You can walk everywhere and do not need a car from this location.  Take advantage of the pedestrian lifestyle in Key West and walk or ride a bike. Remember, this part of the island was developed before there were cars!

Restrictions: Smoke free house. Smoking permitted outside only.  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

2 BR 2 BA

Aug 1- Aug 31

Monthly $5900

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Dates Monthly
Jun 1, 2024 - Jun 30, 2024 $7900
Jul 1, 2024 - Jul 31, 2024 $7900
Aug 1, 2024 - Aug 31, 2024 $6500
Sep 1, 2024 - Sep 30, 2024 $6500
Oct 1, 2024 - Oct 31, 2024 $7900
Nov 1, 2024 - Nov 30, 2024 $8200
Dec 1, 2024 - Dec 31, 2024 $8900
Jan 1, 2025 - Jan 31, 2025 $14050
Feb 1, 2025 - Feb 28, 2025 $14650
Mar 1, 2025 - Mar 31, 2025 $14050
Apr 1, 2025 - Apr 30, 2025 $9900
May 1, 2025 - May 31, 2025 $7900
Jun 1, 2025 - Jun 30, 2025 $7900
Jul 1, 2025 - Jul 31, 2025 $7900
Aug 1, 2025 - Aug 31, 2025 $6500
Sep 1, 2025 - Sep 30, 2025 $6500
Oct 1, 2025 - Oct 31, 2025 $7900
Nov 1, 2025 - Nov 30, 2025 $8200
Dec 1, 2025 - Dec 31, 2025 $8900

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.

  • Front Bedroom  – Queen size bed
  • Master Bedroom – King size bed
Nov 06, 2023,
Absolutely VHKW is the best. We have used them several times and have had no problems. Highly recommend. Will definitely continue to use.

May 11, 2023,
We have rented several properties from VHKW over the last couple of years. The team there are good communicators, and respond quickly to all enquiries. Highly recommend!

Nov 08, 2022,
Great service and excellent to deal with. Highly recommend.

Jun 11, 2022,
Everything was great with our rental (811 Whitehead Street). The place was as advertised per the pictures and information on the listing for monthly rentals. The service from VHKW was excellent as well. The one suggestion would be to allow renters to schedule their mid month cleaning visit in advance vs. scheduling it during the stay.

Apr 06, 2022,
Very accommodating as always !

Apr 07, 2021,
great customer service!

Mar 08, 2021,
This is a very professional organization. They handled my recent rental house with a good contract, good information, and any repairs promptly.

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