Key West Dreamin` - Private Pool Steps Off Duval

Key West, Florida
$748 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

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.

Bedding Summary:

Master bedroom - King size bed
Second bedroom - 2 twin beds (can be made up as a king bed)
Living Room - Queen sleeper sofa
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 TV, stereo, washer / dryer, grill. Linens and towels are provided.

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 and the delightful Key West Butterfly Conservatory. This Uptown neighborhood features art galleries and boutiques, wonderful eateries and internationally famous fine restaurants (Martin`s is just down the street), coffee and tea house, fine gift and clothing stores, Grand Vin wine tasting, Flamingo Crossing home made tropical 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. South Beach and the Southernmost Point are just a 6-minute stroll away from Key West Dreamin`.

Restrictions: Smoke free house. Smoking permitted outside only. No pets. (Please don`t ask!). We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

PAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1066 Sq Ft (99 Sq M)
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Fenced Yard Garden Patio
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    2 Bathrooms Hair Dryer Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Marina Nearby Power Boating Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Jane N.

    Submitted Feb 5, 2026

    Stayed Jan 24, 2026

    Perfect location and well appointed. Very relaxing stay as we escaped the storm in the Northeast. The pool was a lovely backdrop.

  • David B.

    Submitted Jan 25, 2026

    Stayed Jan 17, 2026

    Very comfortable for 4, and great location.

  • Submitted Jan 1, 2026

    Stayed Dec 28, 2025

    Great location! Clear communication and house was clean and cozy. Would rexommendz

  • Kathy R.

    Submitted Dec 19, 2025

    Stayed Dec 14, 2025

    All the above everything was very nice, and clean.the host was very prompt in answering questions..

  • Amanda H.

    Submitted Nov 30, 2025

    Stayed Nov 22, 2025

    Beautiful home and backyard, wonderful location

  • Jason H.

    Submitted Oct 27, 2025

    Stayed Oct 18, 2025

    Great Location.

  • Cheryl L.

    Submitted Oct 20, 2025

    Stayed Sep 25, 2025

    Great house, unfortunately the road was closed everyday of our stay so that was very inconvenient. The house however was great half block off Duval close to amazing restaurants and entertainment. Chickens came right up onto the porch and iguanas by the pool, never a dull moment in Key West!

  • Laura F.

    Submitted Apr 1, 2025

    Stayed Mar 28, 2025

    My friends and I loved our stay at this property and took full advantage of the living space and pool while catching up on our lives. The location couldn’t have been more convenient to shops, bars, and restaurants.Our car did not fit in the one parking space, but we were prepared for that possibility since the listing clearly explains that the space would only fit a compact car (we had a Subaru Outback). Luckily, we were able to grab one of the very few street parking spots near the property upon arrival.

  • Tracy C.

    Submitted Mar 29, 2025

    Stayed Mar 22, 2025

    We loved our time at this property. The house was clean and charming. The location was excellent! We walked everywhere. It was a convenient spot - close to areas of interest, yet a quiet spot to relax and unwind!

  • Kevin R.

    Submitted Mar 14, 2025

    Stayed Mar 10, 2025

    The property was very nice. The location was very close to everything. It’s Not a place to drive to and from venues. However you can uber from the home to further away events. The town is cruise port so on days you may have wait times as thousands of extra people are in town. It’s a beautiful island. The home is very nice for two couples or family’s up to 6 as the couch turns into a bed as well. The pool is nice if you want to get sun on the trip. I recommend going to a beach. The back yard is well shaded. So getting sun doesn’t fit this set up just a few hrs a day. The home was very clean and tidy. Parking is limited to a 15x9 space so if you have a compact or jeep it will fit. Otherwise you will need to find a pay lot to park. On our stay the pool area needed cleaning Powerwashing as it was pretty weathered. Iguanas come and go frequently in the pool area. So be prepared to be startled often. The back fence was falling over and needs repair. the hammock was pretty dirty and we didn’t feel comfortable using it. Yes we would stay here again. It’s a great place and location.

  • Rebecca B.

    Submitted Mar 8, 2025

    Stayed Mar 1, 2025

    Beautiful property, great pool, great location! Well appointed. Weather cooperated which was a plus. Definitely recommend and will stay here again!

  • Ashley E.

    Submitted Jul 15, 2024

    Stayed Jul 7, 2024

    It was a great location, very clean and the rental company was amazing.

  • Mark H.

    Submitted Jun 5, 2024

    Stayed May 29, 2024

    We had a great time and really enjoyed our stay here. Everything was super clean and the location is perfect.

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Total

Includes taxes and fees
$748+
View details