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Key West Dreamin' ~ Downtown Location Near Duval Street with a Private Pool

Bedrooms 2
Property type house
Minimum Stay 3 - 7 nights


About the property

House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)

Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one that links us to our Cuban heritage back to the late 1800's. A stroll through this charming Upper Duval neighborhood is to rendezvous with an important part of our island's rich cigar and rum history.

A Little Bit of History: It is noteworthy that in 1876, one of our most prominent Cuban immigrants, Eduardo H. Gato, built a stunning marble Cigar Factory on the corner of Simonton and Catherine Streets to create the city's largest producing hand-rolled cigar factory. As the cigar industry boomed, so did the immediate need for neighborhood housing. Houses for merchants and workers alike sprang up side-by-side, right to the street, to form the Old Town Key West "Gato" neighborhood which includes Louisa, Catherine, Amelia, Virginia and Simonton Streets; indeed at one point this end of the island was once called "Gatoville."

Located just off Duval on Catherine Street, Key West Dreamin', is an important representation of how the history of our architectural culture is tied to the boom of the cigar industry in the late 1800's. Today the neighborhood is part of Key West's historic preservation district. So the front facade of the houses look very similar to how they originally looked, giving the wonderful effect of maintaining the charm of the neighborhood.

You don't have to smoke Cohibas (flagship brand of Cuban Cigars) or drink Cubra Libras (1.25 oz Rum, and fill with coke and always lime wedge), to enjoy the dynamic impact the early cigar and rum industries had on our architectural culture. Choosing to stay in this historic neighborhood will help take you back to a simpler time in history. Come and enjoy this authentic Key West house in this important part of our island. And why not have rum... And maybe even a cigar.

Interior Layout: The interior of this one-of-a-kind property has been luxuriously renovated and reconfigured to bring the joy of indoor-outdoor pool-garden living to focus. In the fall of 2014, the kitchen and bathrooms received a major renovation for the specific purpose of redesigning it as a luxury vacation rental home.

As you step into the front door, the ‘shot gun’ style hallway leads from the front all the way to the back of the house to the great-room. Eyes are immediately drawn to the back of the house since the back wall is light-filled and gorgeous. A broad bank of French doors and large transom windows span the entire width of the room and the whole effect is made even more dynamic with a soaring cathedral ceiling. The French doors adjoin the great-room to the lushly landscaped back yard and generous size swimming pool.

A beautiful renovation has created the feeling of a grand great-room with soaring open-beamed ceilings and custom transom windows that meet the ceiling. Set to one side of the room, the upscale kitchen offers bright white cabinets, state-of-the-art stainless steel appliances, cream colored granite counter tops, and glistening subway tile back splashes, creating an artistic and functional space. I love the over-sized dining island which is set in the center of everything so you can enjoy the cooking, the large screen TV and turn your gaze to the tropical back deck and swimming pool.

Since the great-room is connected to the outdoors with French doors that extend the entire width of the house, the stage for the indoor - outdoor island lifestyle is set. Whether you choose to cozy inside or lounge around the pool you're always sure to enjoy the quintessential outdoor tropical scene. Just outside the kitchen door, the back yard offers a lovely lounge room complete with an open beam ceiling and shuttered walls making this a unique open-air sitting area that is delightful to enjoy all year around.

The two large bedrooms with en-suite bathrooms are just off the hallway that joins the front to the back of the house. Both bedrooms are made to feel more spacious with open beam cathedral ceilings. Facing the front of the house the master bedroom is to the right. This bedroom offers a king size bed, and in addition to a private bath the master bedroom has a set of French doors that connect it with the back yard and swimming pool.

The second bedroom is a similar design to the master bedroom in that it also has cathedral ceilings and a private en-suite bath. This bedroom situated off the hall to the left as you face the house, offers two twin beds that can be joined to make a king size bed. Bathrooms for each bedroom suite are luxurious and similar in design, donning fabulous Key lime colored granite vanity tops, brilliant white subway tiles, and floor-to-ceiling frameless clear glass walls that create double size shower rooms. A fashion stripe of shining colored glass tiles and designer bath fixtures complete the look.

Grounds: The curb appeal is endearing with a white garden wall and wrought iron fence toppers. The symmetrical entrance is appointed with garden-basket wall statues and is gated with a charming wrought iron gate. Once inside the gate the spacious front porch invites you to pause and "sit a spell" on the porch swing. The front side and back yards are nicely landscaped and artful flagstone has been used to cover the entire grounds.

The original back yard is fully fenced with a white picket fence. A pretty garden trellis holds a showy tropical vine which flowers during different times of the year, and a wide variety of beautiful palm trees and colorful tropical foliage create privacy and a romantic tropical setting. The back yard garden was redesigned to accommodate a nice size swimming pool and flagstone pavers are set throughout the back to create a beautiful garden and sun deck.

The original back yard is fully fenced with a white picket fence. A pretty garden trellis holds a showy tropical vine which flowers during different times of the year, and a wide variety of beautiful palm trees and colorful tropical foliage create privacy and a romantic tropical setting. The back yard garden was redesigned to accommodate a nice size swimming pool and flagstone pavers are set throughout the back to create a beautiful garden and sun deck.

Sleeping configuration:

• Master bedroom - king size bed.

• Second bedroom - 2 twin beds (can be made up as a king bed)

• Queen Sleeper Sofa – in Great Room

Amenities: Swimming pool, large flagstone deck, tropical gardens, front porch with porch swing, privacy fences. Fully equipped kitchen, central a/c, telephone, large flat-screen cable TV, stereo, washer / dryer, grill. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.

Parking: Off - Street Parking for one standard or compact size car. "Big Rigs" won't fit.

Activities: Uptown Key West - Close to the Southern Most Point of the United States and Key West South Beach. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants (Camille's is just down the street), coffee and tea house, fine gift and clothing stores, Grand Vin wine tasting, flamingo Crossing homemade ice cream. Start at the top of Duval St. near the Atlantic Ocean and can take the 20 min stroll to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife.

Restrictions: Smoke free house. Smoking permitted outside only. Absolutely no pets. (Please don't ask!).

Keywords: House

More Details

Property Manager
Vacation Homes of Key West (VHKW)
Speaks: english, czech, Bulgarian
Response time:
Within a few days
Response rate:
Calendar last updated:
November 8, 2017

Guestbook comments from the manager

This place was like heaven. It had it all, everything and more than you would ever need for a week of pure luxury and relaxation. From the quite back patio to the cozy front porch with a swing the place was just full of an at home feeling. Having a private pool and a nice cook out area in Key West gives you the feeling that you are a local and that you belong right were you are. We all would have loved to just move in and live the dream the rest of our lives.
Jun 2013
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Uptown/Upper Duval House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 6
  • Min. age of primary renter: 25
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
  • Please refer to your rental agreement for Cancellation Policy for this property
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 king
    Bedroom 2 - 2 twin/ single , can be made up as a king bed
    Living Room - 1 sleep sofa /futon , Queen sleeper sofa
  • King size beds (1), Twin or Single Beds (2)
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Television
  • Deck / Patio
Pool / Spa:
  • Private Pool
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • eco tourism
  • outlet shopping
  • paddle boating
  • photography
  • shelling
  • shopping
  • shuffleboard
  • sight seeing
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • fly fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • water tubing
  • wind-surfing


5/5 -
(1 traveler reviews)

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Key West Dreamin' ~ Downtown Location Near Duval Street with a Private Pool
average rating of 5.0 based on 2 reviews

Beautiful property

  • 5 of 5

Upgraded property in a great part of town...perfect for one or two couple (s) looking for privacy. Swimming pool area is beautiful. Kitchen and bathrooms all new and very stylish...just all around a perfect little gem.

  • Submitted: Feb 24, 2015
  • Stayed: February 2015
  • Source: VRBO, from HomeAway
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Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $175 + Tax
Processing $75 + Tax
Pool Heat $150
Tax Rate 12.5%

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

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