pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
Key West Time
September 16th
9:57pm · 83°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.


Book Direct For The Best Price Guaranteed

special rates available

Oct 22 - Oct 25

Nightly $500

view all specials

Dates Weekly Nightly Terms
Aug 9, 2021 - Oct 1, 2021 $2710$600.254 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2021 - Oct 21, 2021 $3230$623.004 night min. or 3 night min. 60 days prior to arrival.
Oct 22, 2021 - Oct 31, 2021 $4715$808.507 night minimum
Nov 1, 2021 - Nov 6, 2021 $3230$623.004 night min. or 3 night min. 60 days prior to arrival.
Nov 7, 2021 - Nov 14, 2021 $3600$643.007 night minimum
Nov 15, 2021 - Nov 19, 2021 $3230$623.003 night minimum
Nov 20, 2021 - Nov 28, 2021 $3600$643.007 night min. or 3 night min. 60 days prior to arrival.
Nov 29, 2021 - Dec 17, 2021 $2600$575.754 night min. or 3 night min. 60 days prior to arrival.
Dec 18, 2021 - Dec 25, 2021 $5005$893.757 night minimum
Dec 26, 2021 - Jan 2, 2022 $5885$1009.007 night minimum
Jan 3, 2022 - Jan 14, 2022 $4815$963.004 night min. or 3 night min. 60 days prior to arrival.
Jan 15, 2022 - Jan 21, 2022 $4815$928.754 night min. or 3 night min. 60 days prior to arrival.
Jan 22, 2022 - Jan 28, 2022 $4815$928.755 night minimum - 'within' Sat/Sat Only
Jan 29, 2022 - Feb 18, 2022 $6170$1102.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 19, 2022 - Feb 25, 2022 $6640$1138.507 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 26, 2022 - Apr 17, 2022 $6170$1102.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 18, 2022 - May 29, 2022 $4430$791.254 night min. or 3 night min. 60 days prior to arrival.
May 30, 2022 - Jun 10, 2022 $4220$814.004 night min. or 3 night min. 60 days prior to arrival.
Jun 11, 2022 - Aug 7, 2022 $4700$839.505 night min, but 3-4 nights within 60 days
Aug 8, 2022 - Sep 30, 2022 $3540$784.004 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2022 - Oct 20, 2022 $4220$814.004 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2022 - Oct 30, 2022 $6150$1054.507 night minimum
Oct 31, 2022 - Nov 5, 2022 $4220$814.004 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2022 - Nov 13, 2022 $4700$839.507 night minimum
Nov 14, 2022 - Nov 18, 2022 $4220$814.003 night minimum
Nov 19, 2022 - Nov 26, 2022 $4700$839.507 night min. or 3 night min. 60 days prior to arrival.
Nov 27, 2022 - Dec 16, 2022 $3390$750.754 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2022 - Dec 25, 2022 $6530$1166.257 night minimum
Dec 26, 2022 - Jan 2, 2023 $9595$1645.007 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, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 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
Sep 14, 2021,
Lovely home in Key West right off the main drag. Everything is within walking distance, but rent a golf cart or bicycles if you like. The pool in the back was so nice to relax in at night. The kitchen had everything we needed if we wanted to cook. The beds were very comfortable and the air conditioning was a great escape from the hot 90 degree days. I would love to book Key West Dreaming anytime I visit the Keys.

Aug 23, 2021,
What an awesome place. Everything was perfect!

Jul 28, 2021,
This hour is located just off Duval Street toward the Southern end. It was perfect for our group of four. Well equipped kitchen (not there we cooked with all the restaurant choices on Key West :-). Two bedroom two bath. The pool was the perfect size for us to take a daily dip or two out of the sun. We enjoyed the backyard scenery especially the Iguanas that hang around. The house was very clean. Beds very comfy. Highly recommend this house. We would definitely rent again

Jul 13, 2021,
The house was perfect for our vacation! The house was clean, beds were comfortable, and had everything we needed so we didn't have to eat out everyday. Pool was a perfect size for us and the kids to enjoy before or after our fun on the town. The location was also extremely convenient. We were able to walk to almost everything we wanted to, but had a parking spot if we needed to drive somewhere further away.

Jul 12, 2021,
Enjoyed our stay, cute house with a pool. Communication was great!

Jun 19, 2021,
We had a wonderful time!

Jun 15, 2021,
Great location, loved pool, but was surprised by the green iguana's sunning them self's around the pool. No big deal, they weren't there last time I wend to the keys (long time ago). Everything was nice and clean, and as I said location!

Apr 18, 2021,
We have been going to Key West since 2012 and for all but one year, we have rented through VHKW. They are great to deal with. The place we have stayed almost every year is wonderful.

Apr 12, 2021,
Great rental! This is our 4th rental we've stayed at in Key West and the best one yet. My husband, 12 y/o son and I stayed for a week in March 2021. The house was clean, well equipped with a large outdoor space. Beds were very comfortable which is SO important to us. The pool was fantastic - we had an issue with the pool light but they sent a maintenance man to fix right away after I contacted the management team. Great location - close to Duval but on the quieter south end (which we really liked). Keypad entry so no need to carry keys. My only comment would be to add a hot tub (lol) and this place would be perfect!.

Feb 18, 2021,
We had an incredible time. The house was clean and very warm. The yard was very peaceful and beautiful. Location was second to none. We will be back for sure. Already planning for return next year!!

Jan 02, 2021,
We love this cottage!!! Always immaculate!!! We will stay here again!! Right off Duval but quiet... walking distance to everything!!!

Dec 21, 2020,
We absolutely loved the house and the pool!!! The layout was great with each bedroom having its own bathroom. The weather helped a lot but we will definitely be renting this house again!

Nov 30, 2020,
This is the fourth time we have used Vacation Homes of Key West. The properties are always as advertised. They make booking, check-in and check-out very straightforward and easy. We will definitely use them again when visiting Key West.

Nov 30, 2020,
Such a beautiful home! Perfect location, well appointed, and great customer service from VHKW.

Nov 19, 2020,
522 was lovely and perfectly located. The pool light and other outside lights are on a timer and come on at 7pm until the wee hours of the morning. We left a Keurig behind for the next tenants.

Mar 23, 2020,
This place fit us perfectly Great location, everything in the house was in great shape The pool was heated to our requirements Great place overall!!!

Feb 24, 2020,
An outstanding rental. Vacation Home Key West staff are the best. They make the whole process very easy and pleasant. This was my 10th year back with them. Already looking forward for next year.

Dec 10, 2019,
The Key West Dreamin cottage was just that a dream!!! The cottage was immaculate!!! The kitchen was well stocked with any utensil, pot or pan.The outside was an oasis we even had an iguana visit daily! The past 3 years we’ve stayed in a hotel... Never Again!!! So quiet, private and a few feet from Duval. We will be back Dreamin next year!!!

Dec 03, 2019,
Thank you so much for a perfect vacation spot. Key West Dreamin' was exactly as expected from pics and description online. We could not have found a nicer home to enjoy our wedding / honeymoon week at. Beautifully decorated, great kitchen, huge master with doors to the pool....just idyllic! The parking spot is definitely very small. Only the smallest of compacts would fit, but with options available to park elsewhere, it was not a concern. And VHKW was helpful with all our questions. Looking forward to a return visit!

Aug 03, 2019,
Fourth time staying at Key West Dreaming and it only gets better. The property is immaculate, pool ultra clean, linens, towels, furniture and appliances all top shelf. The team at VHKW are very available for any and all concerns before during and after the stay. I cannot give a higher rating. It's amazing and I will be back!

Jul 19, 2019,
We had a wonderful stay in Key West. Our rental home was beautiful, well-kept and exactly as shown on the website. The staff at VHKW was wonderful to work with and made our stay a breeze. I would highly recommend working with Cindy and her team for your next trip to Key West.

Jun 22, 2019,
Would like to give more stars but 5 is the limit! This home was perfect in every way. First and foremost, it was spotlessly clean! Every cupboard and every corner passed our critical inspection. Kudos to your cleaning staff! The home was conveniently located and walking distance to all the highlights of Duval yet still quiet. Even tho the lots are small and neighbors are close, the beautiful backyard tropical garden afforded pleasant privacy. So that being said, if we had to make a suggestion, it would be to add some hooks or places to hang wet bathing suits and towels either outside or in the bathrooms. In closing.....this place is a jewel!!!

Jun 06, 2019,
We have stayed at the same location for multiple times now and always have the most AMAZING time!! The house is located in a prime area. It's quiet but only walking distances from Duval and tons of exciting entertainment. We absolutely LOVE this house and will definitely be coming back again in the near future! :)

May 20, 2019,
Perfect, private retreat in Key West. There were 4 people in our party and this property fit us perfectly. The pool is bigger than it looks in the pictures and we enjoyed using it every day! The property is in good condition and there were no surprises during our stay. There is even a small, gated area to park rented scooters or a golf cart (which we did). I would not hesitate to recommend this property!

Apr 07, 2019,
Very comfortable home. Relaxing backyard. Great location

Mar 26, 2019,
Beautiful house and backyard space

Feb 25, 2019,
A+++++. outstanding service, and superb staff to work with.

Jan 04, 2019,
We stayed in 'Key West Dreamin' Christmas week this (2018) year. It is a great two bedroom, two bath cottage with a beautiful court yard and medium sized pool. The property is charming and meticulously maintained. It was larger than we needed as a couple but we knew the area and think it is very desirable. You're about a 15 minute walk from Malllory Pier for example . The neighborhood is residential, meaning pretty quiet. The folks at VHKW are pleasant and eager to be of assistance. If you are thinking of renting this one pay attention to the warning about size restrictions on parking. We rented a compact and it was fine but any larger would not fit the drive. Anyway you walk almost everywhere. We had another wonderful week in Key West.

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!!

Inquire Availability for this property
* all fields are required.

Thank you for your inquiry. We will get back to you as soon as possible.

Sort Properties

Rental Period

Availability Calendar

* This property may not be available for the dates above due to other inquires and pending reservation.

Vacation Rentals

Rentals For
Social Distancing

rentals for social distancing

Sunset Key

sunset key






town houses and condos







Truman Annex

truman annex

Golf Club Vacation Rentals

key west golf club