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  • (305) 294-7358
Key West Time
May 28th
11:01am · 87°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 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.


Book Direct For The Best Price Guaranteed

special rates available


June 17 - June 20
June 25 - July 7

Nightly $650
Weekly $3100

view all specials

Dates Weekly Nightly Terms
Apr 13, 2024 - May 29, 2024 $4390$784.004 night min. or 3 night min. 60 days prior to arrival.
May 30, 2024 - Jun 9, 2024 $3925$757.004 night min. or 3 night min. 60 days prior to arrival.
Jun 10, 2024 - Aug 11, 2024 $4390$784.005 night min, but 3-4 nights within 60 days
Aug 12, 2024 - Oct 2, 2024 $3035$625.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $3400$675.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $5785$990.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $3925$755.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $4390$785.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $3925$755.003 night minimum
Nov 22, 2024 - Nov 30, 2024 $4390$785.007 night min. or 3 night min. 60 days prior to arrival.
Dec 1, 2024 - Dec 18, 2024 $3130$675.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $5920$1140.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $6900$1300.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $5790$1050.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $5790$1050.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $5790$1050.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $5930$1090.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $6300$1130.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $5930$1090.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $4390$784.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $3925$757.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $4390$784.004 night min. or 3 night min. 60 days prior to arrival.
Aug 11, 2025 - Oct 1, 2025 $3035$625.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $3400$675.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $5785$990.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $3925$755.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $4390$785.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Nov 11, 2025 - Nov 20, 2025 $3925$755.004 night min. or 3 night min. 60 days prior to arrival.
Nov 21, 2025 - Nov 29, 2025 $4390$785.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $3130$675.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $6150$1180.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $7170$1350.007 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
Dec 06, 2023,
Easy communication. Accurate information

Nov 28, 2023,
Everything was perfect about this cottage! Enjoyed our stay.

Aug 28, 2023,
Eighth time tending the same property. VHKW keeps the house and grounds looking great and ultra clean. Staff provides great communication and are friendly. Already looking forward to next trip as we had to leave early this time.

Aug 14, 2023,
VHKW was a pleasure to work with. Very responsive and offered many suggestions to make our trip the best it could be

Jul 04, 2023,
Great communication, easy check in and check out, fantastic house! Highly recommended.

May 15, 2023,
Love this place

Apr 25, 2023,
We loved the house and enjoyed our stay immensely. VHKW staff was extremely professional and responsive. A couple of suggestions that would enhance the next guest(s) stay. The landscaping/trees could use a good trim and cleanup. Also could use a couple of new frying pans.

Feb 28, 2023,
As always, Key West Dreaming is an amazing place to stay. VHKW staff are the best. Will return for our 14th year!

Dec 26, 2022,
Perfect location! The home was clean, and the pool was fantastic. We would definitely stay here again!

Dec 13, 2022,
We’ve stayed at this house for years & always have had the best time!!! Counting down the days until our next trip!!

Dec 05, 2022,
House and grounds were very nice. House was clean. One improvement opportunity is better pillows.

Nov 15, 2022,
Place was great. Service perfect other than me forgetting items and paying the surcharge. (totally my fault but hefty non the less) it was a fantastic week!

Aug 02, 2022,
Great Stay at Key West Dreamin’ ! Great house and great communication with the staff. Easy check-in also. Hope to use them again in the future.

May 07, 2022,
House was in great shape. Everything was clean and as described. I don’t know that the pool heater worked because the water never got warmer than 82 so I would probably save that $150 next time. Other than that everything was perfect

Mar 11, 2022,
Very nice big & roomy lots of drawers & closets for clothes.

Mar 01, 2022,
As always not enough stars to compliment you all

Jan 27, 2022,
Every thing was fine.

Dec 22, 2021,
We had a few issues at the house we rented but Vacasa was quick to respond

Nov 08, 2021,
Wonderful staff, very helpful and responsive. The house was in great condition and we had a great stress free vacation.

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!Sent by: Teo ( on 16-Jun-21 11:46 AM Delivered Hi Michael, Thank you for your comments! You gotta love the Key West wildlife - between chickens, iguanas and geckos ...they sure are entertaining! :) Glad to hear you enjoyed your stay and the location! We look forward to your next visit!  VHKW Team

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.

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