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About

Monthly Rentals Only
History buffs love to immerse themselves in the centuries old legends of Key West – and if they’re lucky, they’ll find room in Smuggler’s Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the island.

Smuggler’s Den, a delightfully updated, historic, two-bedroom, two-bath Conch cottage is a sweet combination of modern amenities, beautifully landscaped – and private – outdoor space and tall tales of smugglers and outlaws who once roamed the streets of Old Town.

Located on one of Key West’s best streets and in one of its celebrated Old Town neighborhoods, Smuggler’s Den boasts a street-side front porch from which you can watch the neighbors, wondering which of them might be a modern pirate. Its spacious outdoor living areas in the rear of the cottage are perfect for an evening supper with friends or a moonlight dip in the warm, swirling waters of the in-ground spa.

Inside, the light-filled living areas with hardwood floors and welcoming bedrooms and baths flow into an eat-in kitchen. Head out the kitchen door into the walled and landscaped privacy of the outdoor areas. Don’t forget to take your cup of coffee and a book; there are lots of places to curl up and enjoy the sun and dappled shade.

If you’re feeling energetic, grab your bike or walking shoes and head for the beaches at Fort Zachary Taylor State Park, just a few minutes away. Or wander the Historic Seaport, which is equally close. Just a block down the street, you’ll find two of Key West’s best neighborhood restaurants and Fausto’s food market is only a couple blocks away, if you’d prefer cooking in for the evening.

Smuggler’s Den is a perfect home for two with a large second bedroom and bath for visiting family and friends. You may find you’ll never want to leave. As for the smugglers, outlaws and pirates? we won’t promise you’ll meet even their ghosts, but then who knows? Key West is a place where dreams are made.

***Managed by Historic Key West Vacation Rentals***

Features

Amenities

  • Satellite / Cable
  • Television
  • Hot Tub
  • Full Kitchen
  • Coffee Maker
  • Dishwasher
  • Microwave
  • Toaster
  • Cookware
  • Dinnerware
  • Central Air
  • Air Conditioning
  • Ceiling Fans
  • Linens
  • Washer & Dryer
  • Ironing Board
  • WiFi High Speed Internet
  • Iron
  • Hairdryer
  • Private Balcony
  • Private Yard
  • Gas Grill
  • Cable TV
  • WiFi High Speed Internet

Location

  • Historic Old Town

Type

  • House

Length of Stay

  • Monthly

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
June 2018
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July 2018
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August 2018
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October 2018
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January 2019
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Rates

DatesWeeklyMonthly
10/01/18 - 12/31/18$5,572$5,970
01/01/19 - 03/31/19$9,324$9,990

Map

Reviews

Leave a Review

A great vacation place.

Reviewed on2018-01-06 by from Huntington, WV United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The property has a great location, just three blocks from Duval Street. The house was very clean and well appointed. I would recommend this property to other travelers.

A great vacation place.

Reviewed on2018-01-06 by from Huntington, WV United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The property has a great location, just three blocks from Duval Street. The house was very clean and well appointed. I would recommend this property to other travelers.

Managers Response

Thanks Mr. Scott for joining us. We appreciate the feedback and the top score across the board. We look forward to having back as soon as possible.

A Month in Key West

Reviewed on2017-03-15 by from Elkhart, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
We had a great time. Great restaurants. Weather was terrific this year so we spent at least a few hours every day at a beach. We took in some local theater a couple of times which was very good. The great thing about Key West is that there is always something going on somewhere. From this location all you have to do is walk there or ride your bike. It was our second time renting for a month in Key West. It was our first time at Smugglers Cove. The best thing about this property was it's proximity to downtown as well as the Harbor/Marina. It is fairly roomy. We had weekend guests a couple times. It worked out very well. It is fairly well appointed. However, after a month there were a few minor details which would have made our stay more pleasurable. We spent most mornings and early evenings on the front porch. Some landscaping and flowers in the front of the house similar to what is pictured would be nice. Although the kitchen is appointed with new appliances, the washer and dryer in the outdoor storage could be replaced. The gates in front of the property could use some maintenance. These aren't deal breakers, just some suggestions. I can't say enough about how responsive HKWVR was to all of our needs and requests. They were great to work with.

A Month in Key West

Reviewed on2017-03-15 by from Elkhart, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
We had a great time. Great restaurants. Weather was terrific this year so we spent at least a few hours every day at a beach. We took in some local theater a couple of times which was very good. The great thing about Key West is that there is always something going on somewhere. From this location all you have to do is walk there or ride your bike. It was our second time renting for a month in Key West. It was our first time at Smugglers Cove. The best thing about this property was it's proximity to downtown as well as the Harbor/Marina. It is fairly roomy. We had weekend guests a couple times. It worked out very well. It is fairly well appointed. However, after a month there were a few minor details which would have made our stay more pleasurable. We spent most mornings and early evenings on the front porch. Some landscaping and flowers in the front of the house similar to what is pictured would be nice. Although the kitchen is appointed with new appliances, the washer and dryer in the outdoor storage could be replaced. The gates in front of the property could use some maintenance. These aren't deal breakers, just some suggestions. I can't say enough about how responsive HKWVR was to all of our needs and requests. They were great to work with.