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~ SMUGGLER'S DEN ~ Tropical Home w/ Pvt Hot Tub In Heart of 'Old Town' KW

Bedrooms 2
Property type house
Minimum Stay 28 nights


About the property

2 Bedrooms, 2 Baths, Sleeps 4

28 Night Minimum - 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***

More Details

Property Manager
Historic Key West Vacation Rentals
Speaks: english
Manager indicates their response time is:
Within a few hours
Calendar last updated:
January 17, 2018

About Historic Key West Vacation Rentals

Historic Key West Vacation Rentals offers luxury historic vacation rental homes in Key West Florida. Well-trained vacation specialists will guide you through the important process of selecting just the right property for your stay. Whether your party is one of friends or family, or a group celebrating a special occasion, we are eager to help you find the ideal property among our exceptional selection of beautiful accommodations.

Our staff is committed to offering a uniquely personal touch in helping plan ideal independent travel vacations. We are proud of our commitment to first-rate personal service and believe it sets us apart from the rest.

Why Historic Key West Vacation Rentals chose Old Town

Newly Renovated, Great Location, Great outdoor space too!

What makes this house unique

Porch, hot tub, location, immaculate, outdoor space


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Catering available
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 4
  • Min. age of primary renter: 0
  • Parties/events not allowed
  • Non smoking only
Location Type:
  • Downtown
  • Village
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • 2 Bathrooms
  • 2 Bedrooms, Sleeps 4
  • 1 King bed, 1 Queen bed
  • Satellite / Cable
  • Television
  • Deck / Patio
  • Golf
  • Outdoor Grill
  • Tennis
  • Long-term Renters Welcome
Pool / Spa:
  • Hot Tub
  • botanical garden
  • churches
  • cinemas
  • library
  • live theater
  • marina
  • museums
  • restaurants
  • ruins
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • scenic drives
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • rafting
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing


5/5 -
(2 traveler reviews)

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~ SMUGGLER'S DEN ~ Tropical Home w/ Pvt Hot Tub In Heart of 'Old Town' KW
average rating of 5.0 based on 2 reviews
Huntington, WV

A great vacation place.

  • 5 of 5

Rating Details:

The property manager was very helpful.

The vacation rental was spotless.

I was very happy with the location.

I was very satisfied with the condition of the vacation rental.

Overall, I recommend this vacation rental.

Reviewer Comments:

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.

  • Submitted: Jan 7, 2018
  • Stayed: December 2017
  • Source: Historic Key West Vacation Rentals
Owner's 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.
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Elkhart, Indiana / Stevensville, Michigan

A Month in Key West

  • 5 of 5

Rating Details:

The property manager was very helpful.

The vacation rental was spotless.

I was very happy with the location.

I was more than satisfied with the condition of the vacation rental.

Overall, I recommend this vacation rental.

Reviewer Comments:

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.

  • Submitted: Mar 15, 2017
  • Stayed: February 2017
  • Source: HomeAway
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Located in the heart of historic old town Key West


Rates & Availability

Taxes and fees are additional


  • * Please note that this web site may add additional charges to your quote that are not collected by our company.
    * To eliminate the 3% credit card fee call our office and arrange for payment by check
    * International customers may pay with a wire transfer call our office to make arrangements
    * Rates subject to change until reservation is confirmed
    * Higher rates apply to holidays and special events
    * Minimum age requirement of 25
    * No Pets unless specified, No Smoking
    * If you do not select the $45 damage insurance, a $3000 refundable security deposit will be required
    * Call or email our office if your dates do not meet the required minimum, we may be able to honor a shorter stay
    * If your requested dates are not available or the price quote function fails - email or call us, we may have another property for you

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