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  • (305) 294-7358
Key West Time
December 17th
10:42am · 64°F

Key West Dreamin' ~ Weekly Rental

2BR 2BA ~ Weekly Rental
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.

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 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 home made 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. 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.


special rates available

Dec 12- Dec 15
Nightly $450

Jan 27- Feb 2
Weekly $3800

view all specials

Dates Weekly Nightly Terms
Nov 24, 2018 - Dec 19, 2018 $2300$5504 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2018 - Dec 28, 2018 $4100$7007 night minimum
Dec 29, 2018 - Jan 4, 2019 $4800$8007 night minimum
Jan 5, 2019 - Jan 11, 2019 $3825$7004 night min. or 3 night min. 60 days prior to arrival.
Jan 12, 2019 - Jan 18, 2019 $3925$7004 night min. or 3 night min. 60 days prior to arrival.
Jan 19, 2019 - Jan 25, 2019 $3925$7004 night min. or 3 night min. 60 days prior to arrival.
Jan 26, 2019 - Feb 1, 2019 $3925$7005 night minimum - 'within' Sat/Sat Only
Feb 2, 2019 - Feb 15, 2019 $4025$7007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 16, 2019 - Feb 22, 2019 $4325$7007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 23, 2019 - Apr 19, 2019 $4025$7007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 20, 2019 - May 26, 2019 $3300$6004 night min. or 3 night min. 60 days prior to arrival.
May 27, 2019 - Jun 14, 2019 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Jun 15, 2019 - Aug 8, 2019 $3300$6005 night min, but 3-4 nights within 60 days
Aug 9, 2019 - Oct 19, 2019 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Oct 20, 2019 - Oct 26, 2019 $4300$8007 night minimum
Oct 27, 2019 - Nov 3, 2019 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2019 - Nov 10, 2019 $3300$6007 night minimum
Nov 11, 2019 - Nov 22, 2019 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Nov 23, 2019 - Nov 29, 2019 $3300$6007 night minimum
Nov 30, 2019 - Dec 20, 2019 $2350$5504 night min. or 3 night min. 60 days prior to arrival.
Dec 21, 2019 - Dec 27, 2019 $4175$7007 night minimum
Dec 28, 2019 - Jan 3, 2020 $4875$8007 night minimum
Jan 4, 2020 - Jan 10, 2020 $3875$7004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2020 - Jan 17, 2020 $3975$7004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2020 - Jan 24, 2020 $3975$7004 night min. or 3 night min. 60 days prior to arrival.
Jan 25, 2020 - Jan 31, 2020 $3975$7005 night minimum - 'within' Sat/Sat Only
Feb 1, 2020 - Feb 14, 2020 $4075$7007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 15, 2020 - Feb 21, 2020 $4375$7007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 22, 2020 - Apr 18, 2020 $4075$7007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 19, 2020 - May 25, 2020 $3300$6004 night min. or 3 night min. 60 days prior to arrival.
May 26, 2020 - Jun 13, 2020 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Jun 14, 2020 - Aug 7, 2020 $3300$6005 night min, but 3-4 nights within 60 days
Aug 8, 2020 - Oct 18, 2020 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Oct 19, 2020 - Oct 25, 2020 $4350$8007 night minimum
Oct 26, 2020 - Nov 2, 2020 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2020 - Nov 9, 2020 $3300$6007 night minimum
Nov 10, 2020 - Nov 21, 2020 $2950$5504 night min. or 3 night min. 60 days prior to arrival.
Nov 22, 2020 - Nov 28, 2020 $3300$6007 night minimum
Nov 29, 2020 - Dec 19, 2020 $2350$5504 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2020 - Dec 26, 2020 $4225$7007 night minimum
Dec 27, 2020 - Jan 2, 2021 $4925$8007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, New Years, Key West Yacht Race Week, Thanksgiving, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, Biker's Poker Run, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

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.

  • Master bedroom - King size bed
  • Second bedroom - 2 twin beds (can be made up as a king bed)
  • Living Room - Queen sleeper sofa
Nov 28, 2018,
Perfect in every way!!!

Nov 26, 2018,
Vacationed with our sons (25 & 28} ...loved every minute of it! The home is beautiful and very convenient to everything. We enjoyed the outdoor space as much as the inside. We will defiantly visit again!!

Oct 11, 2018,
We enjoyed our time at Key West Dreaming . Although it was very near the Duval Street action, it seemed like a quiet oasis. The kitchen was well equipped, the beds were comfortable. We especially enjoyed sitting by the pool for cocktails and meals. KWD is a charming and comfortable retreat in Key West.

Sep 21, 2018,
The customer service was excellent. Each time I called I reached someone and any questions I had prior to arriving were answered. The house was perfect- clean, cozy. It was great not to have to stop by anywhere and check in first. It was easy to get ready to leave and check out. The VHKW staff even assisted with a baggage issue that we had before leaving.

Aug 28, 2018,
My third time staying with VHKW and I must say the team is simply amazing from reservation to check in to check out. The property was amazing with all the highest quality amenities, ultra clean and supremely comfortable. I honestly wouldn't consider staying anywhere else. Thanks to Finlay and Ginnette for making my trip to my favorite place amazing as usual. Already trying to plan on coming back.

Jul 31, 2018,
Key West Dreamin’ was the best part of our trip! The location is perfect and the outdoor space is nicely shaded with a pool that is larger than appears in the pictures. The house is well stocked and the beds are comfortable. My only constructive feedback is that the pull-out sofa mattress has seen better days and should be replaced, as well as the two chairs in the living room (the leather upholstery is wearing off). We had 5 adult women in the house and it was comfortable, however 6 may seem crowded. All-in-all a great house, cold A/C, awesome pool and outdoor space and modern kitchen/bathrooms. I’d stay here again!

Jul 09, 2018,
Could not have been a better place to stay. Great house and outdoor area with pool. Perfect location. 100 our of 100!

Jun 18, 2018,
We loved this beautiful home! It was roomy and comfortable. It's more southern location made it quiet, yet still a short walk to the buzz of Duval Street. There was plenty of closet space and also a very comfortable bed! I really appreciated that the rooms had shutters so would stay dark in the morning (this is often lacking in KW homes). The outdoor space was equally phenomenal. There is a covered seating area with comfortable furniture and a fan, and the pool is a good size. The backyard and pool area were very private, with privacy fences and lush green landscaping. The house was in very nice shape but time to replace the living room chairs. A/C worked well. An increasing number of good places to eat and drink in the immediate vicinity. Definitely recommend the comedy club at the end of the block - we saw a great show! THIS IS HANDS DOWN OUR FAVORITE HOUSE SO FAR IN 10 YEARS OF VACATIONING IN KEY WEST! We had excellent customer service from VHKW. The only constructive comment is to re-stock kitchen items over time things break or go missing of course eg lids for pots/pans, dinner plates, pitchers, there's a base but no pitcher for the blender. THANK YOU FOR A WONDERFUL VACATION!

Jun 02, 2018,
We loved this cute little cottage. Very clean and well kept. The modern appliances and updated style left us without a want or care in the world. We had everything we needed. It felt like home. The pool was amazing! I would highly recommend this place! We will definitely be coming back to our little Honeymoon Oasis!!

May 01, 2018,
Key West Dreamin' met all of our expectations and then some. The house was spotlessly clean and well supplied with towels, paper products, laundry detergent, etc. The king bed in the master bedroom was incredibly comfortable, and the bathrooms were well-designed with plenty of shelf space. The living area and kitchen were light-filled and lovely, but what we liked most of all was the outdoor pool area. It was lushly landscaped with tropical plants and palm trees, and there were many shady spots for dining, reading, and relaxing. The outdoor furniture was very nice, and the pool was the perfect size, i.e., not too small. We paid extra for the pool to be heated, which made it quite comfortable for early morning or evening swimming. The location was great, too, with the wonderful French bakery, La Grignote, just around the corner. Easy walking to everything, iguanas in the palm trees, and rum drinks by the pool made it an ideal getaway!

Apr 04, 2018,
Four of us have rented Key West Dreamin' for a week in March for 7 years now. The house is perfect for 2 couples. Bedrooms and ensuite are practically identical. The outdoor space with the pool is just the perfect get away from Pensylvania winter. Old town is the quiet end of Key West, but you can still walk or ride to get to any of the action! VHKW makes it very easy to rent. They give you a detailed information package for first-timers and communication is very easy. This year we had lovely flowers awaiting us at the house. Nice touch!

Mar 22, 2018,
We loved our stay in Key West: the location was perfect (near Duval but on the quieter end), and the home was perfect for 2 couples! Both bedrooms with their own bathrooms and the living room and kitchen were open and just enough room, but not too big. the pool and outside grounds were in excellent shape!

Oct 27, 2017,
Not sure how to begin this review. The staff during a terrible time in their lives they were there for the people who had purchased a vacation home. What a tribute!! As for “key West Dreaming “ it was a dream! Perfect and clean in so many ways. 10 days after opening the city, you never knew a hurricane had tried to do the worst. It was like it was never there!! If your looking for a vacation home to rent look no further than VHKW. It’s not our first time with them but it’s definitely not the last. See you next year!

Jul 24, 2017,
The house that we rented in Key West was absolutely perfect! It was spacious enough for 6 adults. Everything is updated and beautifully decorated. Everything and anything we needed was supplied to us in the kitchen. The pool area was wonderful and relaxing especially after a long hot summer Key West day. Location is always important in KW and this little perfect house was located just 1/2 block from Duval. Cold A/C, plenty of parking, location... could not of asked for anything better!

Feb 26, 2017,
very nice place in an excellent location in Key West, will do it again

Feb 22, 2017,
Key west dreaming is a stunning villa in upper Duval area. The service provided by vacation homes key west is outstanding

Feb 13, 2017,
Wonderful time in Key West! Our home was clean,updated, private backyard with a pool, and provided my wife and I memorable time. I would highly recommend the home we rented to anyone. Paige, our representative from VHKW helped to arrange a wonderful sunset cruise. Just a great time!

Jan 16, 2017,
We definitely hope to come back. Bedrooms spacious and great for 4 adults. Kitchen and living area larger than in photos. Grounds and pool well maintained. Concise direction from maintenance when breaker tripped - panel behind bedroom door. Area quiet even though only 1/2 block walk to Duvall Street. Room to have Christmas eve dinner for 9 adults on patio. Also fit Jeep Renegade in parking space behind gate, nothing larger would fit. Turned out to be a most relaxing vacation. Thank you and your staff for a very enjoyable and memorable experience.

Dec 13, 2016,
Beautiful Place! Great location! We would definitely stay here again!

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