Twice as Nice on Duval Street ~ Weekly rental

Standard Rates: $5100 - $10150 per week
4BR 4BA Sleeps up to8
Private Pool

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, telephone, color cable TV, stereo, 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.






Dates Weekly Nightly Terms
Nov 28, 2023 - Dec 16, 2023 $5255 $1015.00 4 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2023 - Dec 25, 2023 $8275 $1477.75 7 night min. or 3 night min. 60 days prior to arrival.
Dec 26, 2023 - Jan 2, 2024 $9705 $1663.75 7 night minimum
Jan 3, 2024 - Jan 12, 2024 $7040 $1355.00 4 night min. or 3 night min. 60 days prior to arrival.
Jan 13, 2024 - Jan 19, 2024 $7040 $1355.00 4 night min. or 3 night min. 60 days prior to arrival.
Jan 20, 2024 - Feb 2, 2024 $7430 $1425.00 4 night min. or 3 night min. 60 days prior to arrival.
Feb 3, 2024 - Feb 16, 2024 $8275 $1500.00 5 night min, but 3-4 nights within 60 days
Feb 17, 2024 - Feb 23, 2024 $8790 $1575.00 5 night min, but 3-4 nights within 60 days
Feb 24, 2024 - Apr 12, 2024 $8275 $1500.00 5 night min, but 3-4 nights within 60 days
Apr 13, 2024 - May 29, 2024 $6385 $1140.00 4 night min. or 3 night min. 60 days prior to arrival.
May 30, 2024 - Jun 9, 2024 $5815 $1100.00 4 night min. or 3 night min. 60 days prior to arrival.
Jun 10, 2024 - Aug 11, 2024 $6385 $1140.00 5 night min, but 3-4 nights within 60 days
Aug 12, 2024 - Oct 2, 2024 $5245 $915.00 4 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $5645 $915.00 4 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $9200 $1575.00 7 night minimum
Oct 28, 2024 - Nov 3, 2024 $5815 $1120.00 4 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $6385 $1150.00 7 night minimum
Nov 12, 2024 - Nov 21, 2024 $5815 $1120.00 3 night minimum
Nov 22, 2024 - Nov 30, 2024 $6385 $1150.00 7 night min Sat/Sat Only, but 3-5 nights within 60 days
Dec 1, 2024 - Dec 16, 2024 $5255 $950.00 4 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2024 - Dec 25, 2024 $8690 $1600.00 7 night minimum
Dec 26, 2024 - Jan 2, 2025 $10150 $1960.00 7 night minimum
Jan 3, 2025 - Jan 10, 2025 $0 $0.00
Jan 11, 2025 - Jan 17, 2025 $0 $0.00
Jan 18, 2025 - Jan 31, 2025 $0 $0.00
Feb 1, 2025 - Feb 14, 2025 $0 $0.00
Feb 15, 2025 - Feb 21, 2025 $0 $0.00
Feb 22, 2025 - Apr 11, 2025 $0 $0.00
Apr 12, 2025 - May 28, 2025 $0 $0.00
May 29, 2025 - Jun 8, 2025 $0 $0.00
Jun 9, 2025 - Aug 10, 2025 $0 $0.00
Aug 11, 2025 - Oct 1, 2025 $0 $0.00
Oct 2, 2025 - Oct 16, 2025 $0 $0.00
Oct 17, 2025 - Oct 25, 2025 $0 $0.00
Oct 26, 2025 - Nov 2, 2025 $0 $0.00
Nov 3, 2025 - Nov 10, 2025 $0 $0.00
Nov 11, 2025 - Nov 20, 2025 $0 $0.00
Nov 21, 2025 - Nov 28, 2025 $0 $0.00
Nov 29, 2025 - Dec 16, 2025 $0 $0.00
Dec 17, 2025 - Dec 25, 2025 $0 $0.00
Dec 26, 2025 - Jan 2, 2025 $0 $0.00
  • 3 queen size beds
  • 1 king size bed
  • Each bedroom is a suite with its own en-suite luxury bath
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