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  • (305) 294-7358
Key West Time
June 16th
5:47am · 85°F

Twice as Nice on Duval Street ~ Weekly Rental

4BR 4BA ~ Weekly Rental
Sleeps 8

In this case... "Two is definitely better than One"! A rare set of early 1900's "twin-cigar maker's cottages" perched on the southern end of famous Duval Street. The Twice As Nice vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge together in luxury and yet require the maximum privacy offered with four separate upscale suites. The exterior beauty of this charming property is undeniably in its historic simplicity. Inside the beauty is not only reflected in the subtle color palette and elegant furnishings, but also through the thoughtfulness of the designer-builders when they transformed the lay-out to meet today's standards for a first-class resort accommodation.

Early Key West Combo: Twice As Nice is a rare combination of an historic "twin-set" of cigar maker's cottages that were originally built to match each other in the early 1900's. This type of "double design" is infrequently found around Key West within the prolific collection of turn-of-the-century wooden cottages built on the island by early ship builders. Located within a neighborhood close in proximity to the gloriously restored historic 8000 square foot building, originally constructed as Gato Cuban Cigar factory, the twin-cottages were first built in the early 1900's as part of hand-made housing for workers of the former factory. Today both the twin-cottages and the Gato building are completely gentrified, but their historic facades and location stand true as testimonies to the colorful economic Caribbean past of Key West.

Modern Transformation: The most recent transformation of the twin cottages to make them Twice As Nice was completed in 2008 and was designed so that they function either separately, or together as one - equally as well. Separately they are known as Havana Moon and Cockadoodle Cottage. When rented together as one accommodation, we call it "Twice As Nice" because indeed it is just that...providing four spacious bedroom suites (each has a custom designer en-suite bath), two gourmet quality kitchens, one private swimming pool with fenced back yard, two connected front sitting porches with a view of the ocean near the southernmost point of the United States, and private off-street parking! I also enjoy the convenience of a local's favorite coffee and tea house in a charming old house across the street - a bit like having a gourmet espresso and pastry "lobby breakfast service."

Interior Layout: In its new look the interior design and decorum of the twin-cottages bespeak the contemporary island romantic minimalist look, i.e. understated and elegant with a tropical feel. Appointed with classy furnishings, subtle colors and quiet artwork to set a tone of calmness and relaxation, floors are an intermixed use of wood and tile, and high ceilings with recessed lighting that give the rooms a more spacious feeling. Even though the interior is completely re-mastered to make four luxurious bedroom suites, two full kitchens, and two master bathrooms (one with double size handicap accessible shower and one with Jacuzzi tub), the owners were true enough to the original interior structure so that you can still enjoy the authentic flavor of the single "shot-gun" design. The classic layout of each cottage essentially mirrors its twin.

Let's begin our "walk-through" of Twice As Nice at the entrances located on the connected front porches. Facing the property, the Havana Moon cottage is the one on the left and the Cockadoodle Cottage is on the right, and front doors are on the left side of each building. Interiors of each cottage pretty much mirror each other in the sense that the basic layout stays true to the original "shot-gun" style.

Upon entering the front door of each cottage you step immediately into the common "hall room" that heads straight-away to the back door. Off this main "common room", on the side of each house, a symmetrical row of interior rooms proceed from the front to the back.

Starting at the front, the first door off the hall of each cottage leads to a front bedroom with custom en-suite bathroom. The front bedroom in the Havana Moon cottage offers a queen size bed and the front bedroom in the Cockadoodle Cottage provides a king size bed. Furnishings are tasteful and elegant in each cottage and compliment one another.* (see notes)

The next room in each cottage is a brand-new modern "U-shaped kitchen," complete with top-of-the-line appliances and recessed lighting. Kitchens in each cottage are open to a wide "sitting hall" which at this point opens to be a small interior gathering and common seating space for each house and makes a natural place for entertaining.

The last rooms down the hall of each cottage we find a spacious back bedroom and custom luxurious en-suite bathroom. Each back bathroom offers a unique feature with Havana Moon providing an oversized and double wide handicap accessible shower while the Cockadoodle Cottage provides a 2 person Jacuzzi bath tub. Finally, at the end of the hall of each cottage are the back doors where it's time to check out the fenced back yard.

Outside Layout: To meet modern luxury vacation standards, the original back yard on the Havana Moon side of the property has been remade to a accommodate a nice size swimming pool and large concrete sun deck for pool-side sunning. The other side of the yard has a small back porch. Back around to the front of the property, is the long covered front sitting porch where you can catch a view of the ocean and the soft salt southern breeze. Pretty wicker furnishings have been placed for guests to sit and watch the world of Key West go by.

Bedding Summary:

  • 3 queen size beds, 1 king size bed
  • Each bedroom is a suite with its own en-suite luxury bath

Amenities: Upscale renovation and luxury furnishings. Swimming pool, large deck, tropical plantings, completely fenced. Two fully equipped kitchens, central a/c, smart TV, washer / dryer. Linens and towels are provided. Off Street parking for 2 cars!

Activities: Elegant Upper Duval St. - Close to the Southern Most Point of the United States. The beach is just down the street to your left, so when you've had enough pool and porch time you can head for South Beach for some sun and good food. There is a great open air beach side restaurant there with a full bar and excellent beach side menu. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee house, fine gift and clothing stores, Grand Vin wine tasting, home made ice cream. Here you 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.

Area: Upper Duval or ‘Uptown Key West’ has evolved into the “elegant end of Duval” and offers an exceptional variety of restaurants, beautiful boutiques, and art galleries.  Close enough to South Beach that you can see it from the porch, and the Southernmost Point of the United States is just around the corner.  Walk to the Mallory Square Sunset Celebration in 15 to 20 minutes.

Restrictions: Smoke free house. Smoking permitted outside only. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. This property is not appropriate to stage loud parties. As with all private vacation homes, occupants of this property must adhere to the Sound Control / Noise Ordinance of Key West - ARTICLE IV Sec. 26-191. No pets please.

*Notes: This property is ideal for couples, professionals, executives, and families who have discerning tastes looking for a luxurious accommodation. One of the cottages in this group, the Havana Moon cottage may not be appropriate for children due to its location. Please contact us for more information.

Payment by credit card will be subject to 3.85% surcharge.




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June 30 - July 15
Nightly $925

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Dates Weekly Nightly Terms
Jun 10, 2024 - Aug 11, 2024 $5815$1100.004 night min. or 3 night min. 60 days prior to arrival.
Aug 12, 2024 - Oct 2, 2024 $5245$915.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $5645$915.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $9200$1575.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $5815$1120.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $6385$1150.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $5815$1120.003 night minimum
Nov 22, 2024 - Nov 30, 2024 $6385$1150.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Dec 1, 2024 - Dec 18, 2024 $5255$950.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $8690$1600.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $10150$1960.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $7320$1400.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $7320$1400.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $7710$1475.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $8575$1550.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $9090$1625.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $8575$1550.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $6385$1140.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $5815$1100.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $5815$1100.004 night min. or 3 night min. 60 days prior to arrival.
Aug 11, 2025 - Oct 1, 2025 $5815$1100.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $5245$915.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $9200$1575.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $5815$1120.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $6385$1150.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $5815$1120.003 night minimum
Nov 21, 2025 - Nov 29, 2025 $6385$1150.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $5255$950.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $9040$1650.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $10500$2000.007 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.

  • 3 queen size beds
  • 1 king size bed
  • Each bedroom is a suite with its own en-suite luxury bath
Apr 17, 2023,
This is our second time staying at this house and we love the location, the pool and the responsiveness of VHKW when needed. We will definitely be returning!

Jul 13, 2022,
The twin cottages were perfect for our group! They were in a fantastic location- walking distance to everything! The pool was a much needed bonus during the hot days.Sent by: Info ( on 20-Jul-22 1:46 PM Opened Thank you so much! We are happy you enjoyed your stay.

Feb 07, 2022,
We stayed at Twice as nice, it was perfect for us. The checkin process was seamless. We loved the location. The property is kept up.

Jan 09, 2022,
Great time and the house was exactly what we expecting! VHKW is a wonderful company to work with.

Nov 08, 2021,
Easy and straightforward to work with! Place was clean and any issues we had were taken care of quickly!

Aug 23, 2021,
I rented Twice as Nice. The location was perfect, both homes were clean, having the pool was awesome, and vhkw was so helpful. Our family had a great vacation. Thanks so much!

Jul 12, 2021,
The rental properties were clean, comfortable and conveniently located on Duval street. The pool was a big hit and an added bonus. I highly recommend this rental property and would gladly stay again.

Feb 16, 2021,
I love the updates that have been made to the Havana Moon. Fresh paint and updated linens made a big difference. Pool was great. We really enjoyed our stay. Thank you all!

Nov 21, 2020,
Everyone I spoke with at VHKW was fantastic! Willing to work with me to get the reservations complete, while I was working with my group on the final details. VHKW provided excellent maintenance when we called for minor issue with AC in the unit. Also appreciated the email we received from VHKW while on property when a hurricane warning was issued, giving us some tips on how to prepare, etc. Regarding the property itself, we stayed at Twice as Nice on Duval. It was perfect for our group of 7 adults. Units were very clean inside and out. Appreciated having a private pool. We loved the porch for people watching!

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