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  • (305) 294-7358
Key West Time
April 23rd
8:12am · 74°F

The Grand Marshall ~ Monthly Rental

5BR 4.5BA ~ Monthly Rental
Sleeps 10

I have a true confession - My husband and I love going on extended vacations with our grown children and grandkids. But we also treasure our own space - if you know what I mean. The combination of this 5BR 4.5 BA Grand Marshall monthly rental is exactly what we look for when we book an upscale, beautifully decorated vacation rental for all of us.

This perfect combo of two upscale renovated homes, On Hemingway’s Rounds, and Governor’s Retreat, are ideally situated on separate lots with fenced backyards that border with each other. When you rent both, you get twice the space, double the privacy, two master suites, two swimming pools, two spacious sundecks, multiple covered sitting porches (with views), two kitchens, plus two off-street parking spaces, and will undoubtedly double the relaxation, and fun!

On Hemingway’s Rounds, is a perfectly redesigned 1-story 2BR 2BA American Bungalow circa 1920. Here you enjoy a Key West cottage which provides an open-concept living room / dining / full kitchen, a master bedroom with en-suite bathroom, and 2nd bedroom with en-suite bathroom. The master suite is at the back of the house, and has the winning feature of sliding glass doors that leads to the pool deck. Outside, in the front of the house, there's a covered sitting porch that runs the width of the house. In the fenced back yard, there’s a sundeck and swimming pool. On the other side of the back fence, we find the 2-story 3BR 2.5 bath, Governor’s Retreat.

Situated back off the street, on a small-picturesque lane, Governor’s Retreat is a 2-story house, and offers 1st and 2nd floor front covered porches with charming views of the neighborhood. When you stay here, you’ll have the spacious 1st floor great room with equipped kitchen, dining area, and comfy living room at the back, adjoining the poolside deck.  When it’s time for bed, the 3 bedrooms and 2 bathrooms are upstairs. You may have to flip a coin for the master bedroom suite on the 2nd floor, as it has an en-suite bath. Plus - the master suite also harbors a closed-in private porch room, with a fabulous view of the swimming pool below.

The focal point of this combined property of 2 homes, is the remarkable indoor / outdoor island living space made possible by combining the back yards with 2 unique swimming pools, spacious back decks, and multiple covered porches. Another fabulous feature is that one house places you on famous Whitehead Street, where you can people watch from the front porch; the other house stations you on a quiet less traveled lane. Where they meet in the back, you can create an outdoor world all your own.

Bedding Summary:

On Hemingway’s Rounds

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

Governor’s Retreat

  • Master Bedroom – King size bed
  • Bedroom Two – Queen size bed
  • Bedroom Three – Queen Size bed

Amenities: 2 private swimming pools, 2 fenced tropical landscaped yards, 2 sundecks, multiple covered porches with views, 2 master bedroom suites, 2 kitchens/ living rooms/ dining areas. Flat screen TV’s in each living room and each bedroom, 2 washer / dryer units. 2 BBQ grills on the back decks, Linens and towels are provided, Catering can be arranged. Periodic maid service is scheduled.

Activities: Here you’re in the Whitehead St. corridor area, where downtown Old Town meets Bahama Village. There are countless 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 famous bars and restaurants. Here you’re close to famous Olivia Street in Bahama Village, Mallory Square Sunset Celebration, the Southernmost Point of the United States. Fort Zachary Taylor Beach is a short walk away. Short walk to the Historic Seaport for sailing, boating, diving, and more restaurants, bars, shopping and night life.

 Area: Located where the downtown Old Town Key West and Bahama Village neighborhoods meet, here you’ll stay less than a block from the Hemingway House and Museum, where Papa lived and wrote in the 1920’s. Only a few-minute walk to famous hip eateries like the Moon Dog Café’ and Blue Heaven, famous bars like The Green Parrot Bar and Sloppy Joe’s, from here you can easily stroll to all the numerous downtown features Key West has to offer. You’re also not far from the Mallory Square dock, Fort Zachary Taylor State Park Beach and the Truman Waterfront Park, featuring the Key West Amphitheater, a Splash Pad for the kids and the Florida Keys Eco-Discovery Center for the whole family.

Notes: This combined 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: There is off-street parking for two cars in the bricked driveway of Governor’s Retreat. You could fit a compact and a large car. However, at this location you will not need a car unless you want to drive to New Town to buy groceries or drive up the Florida Keys. You can have groceries delivered, and you can easily get an Uber or a Cab – park your car, lock it, and forget about it. Enjoy walking or bicycling around Key West. It’s a tiny island, and this neighborhood was built for pedestrians.

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.

Book Direct For The Best Price Guaranteed

Dates Monthly
Apr 1, 2024 - Apr 30, 2024 $21400
May 1, 2024 - May 31, 2024 $16400
Jun 1, 2024 - Jun 30, 2024 $16400
Jul 1, 2024 - Jul 31, 2024 $16400
Aug 1, 2024 - Aug 31, 2024 $13500
Sep 1, 2024 - Sep 30, 2024 $13500
Oct 1, 2024 - Oct 31, 2024 $16400
Nov 1, 2024 - Nov 30, 2024 $16700
Dec 1, 2024 - Dec 31, 2024 $18750
Jan 1, 2025 - Jan 31, 2025 $33550
Feb 1, 2025 - Feb 28, 2025 $34850
Mar 1, 2025 - Mar 31, 2025 $33550
Apr 1, 2025 - Apr 30, 2025 $21400
May 1, 2025 - May 31, 2025 $16400
Jun 1, 2025 - Jun 30, 2025 $16400
Jul 1, 2025 - Jul 31, 2025 $16400
Aug 1, 2025 - Aug 31, 2025 $13500
Sep 1, 2025 - Sep 30, 2025 $13500
Oct 1, 2025 - Oct 31, 2025 $16400
Nov 1, 2025 - Nov 30, 2025 $16700
Dec 1, 2025 - Dec 31, 2025 $18750

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.

On Hemingway’s Rounds

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

Governor’s Retreat

  • Master Bedroom – King size bed
  • Bedroom Two –  Queen size bed
  • Bedroom Three – Queen Size bed
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