pinterest facebook twitter youtube google my business
  • (305) 294-7358
Key West Time
September 18th
5:39am · 84°F

Penthouse On Duval ~ Weekly Rental

4BR 4BA ~ Weekly Rental
Sleeps 8

Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic of the 700 block of Duval Street below, you're sure to capture the 'urban life' that stirs this tiny tropical island.

The Way It Was: If you've ever strolled up bustling Duval Street in downtown Key West, then you've also been touched by the timeless charm of historic Key West-Victorian structures that house the local establishments. Peaked tin roofs, horizontal wood siding and enchanting gingerbread trim were classic trade marks when these early 1900's downtown buildings were first built. And one popular property design embodied a mercantile space below with a residential home 'up top', complete with wide covered sitting porches designed for gazing below at the 'comings and goings' of island life. Nowadays, while most of the 2nd floor spaces on Duval Street have turned completely mercantile, an exceptional few have kept their 'up top' residential spaces. If you set your gaze to the upstairs sitting porches, you can't help but imagine what it must be like to live up there with a 'bird's eye view' of the street. And in the case of this "Penthouse On Duval" its pure dream-worthy pleasure inside... and now you have the opportunity to stay here and experience it for yourself!

The Way It Is: Two things became clear to the owner-designer when she first caught glimpse of this 2nd floor centurion space. One was that this remnant of a 19th century abode was right in the center of Duval Street and would make an absolute ideal Key West vacation rental; while the other was that it had been through too many years of wear and neglect and would require a complete and total make-over. But the Alabama based artist-owner (who has re-designed several properties she owns with her husband) is no stranger to creative challenges. They both love the Caribbean ambience of Key West and it's historic architecture, and after several years of diligent planning and undying tenacity through a myriad of 'renovation wars' they've completed the daunting challenge of turning an 'old sows ear into a stylish silk purse'!

When you walk through the newly designed interior space the rooms artistically unfold before you with a colorful spirit that is at once playful and downright deluxe. Each and every room is unique in design and each is set with beautiful furnishings, custom wall colorings and floors, and unique and colorful island art work. Even the powder rooms in this property stand as gorgeous little 'art alcoves' that reflect the artist-owners commitment to bringing art into everyday life activities.

Layout: Since the exterior of this Old Town building is under the protective eye of the Key West Historic Architectural Review Committee (HARC), the Duval Street facade must always retain its historic persona to help preserve the original character of the island. In order to re-design the upstairs to become luxurious and spacious, permission was obtained to increase the height at the back of the building to create two floors of living inside plus a private back deck outside, with parking beneath. The main entrance to the penthouse is from the back of the building. A traditional wooden staircase takes you to the second floor where you will find your colorful hidden haven. 

With a commitment to historic preservation and modern day comfort, the Key West rental was thoughtfully reconfigured so that it can be rented as one larger 4 bedroom unit or as two separate 2 bedroom units. When rented separately, an inconspicuous 'lock out' door in the central hall works to securely divide the property.

City Island View - Situated on the Duval Street side of the building, this festive Key West rental unit features the original front porch that spans the width of the building with a commanding 'front and center' view of the 700 block of Duval Street below. The porch connects to the stunning great room which has soaring open beam ceilings with designer lighting and tan wicker paddle fans. The owner-artist hand selected a wonderful selection of eclectic furnishings to pull the entire presentation together. Custom colors and unique artwork take their cue from the Caribbean Sea with vivid turquoise walls and oversized diagonally placed sand colored floor tile. I love how the owner has paired the oversized curvaceous cream colored sectional with the round dark wood accent tables, and how a playfully painted artisan dining table is set off with traditional white wicker dining chairs. A collection of unique lamps and carefully chosen artwork complete the perfect great room picture.

The fully equipped designer kitchen flows easily from the dining area with a tiled breakfast bar and two chair back stools. Gorgeous mahogany cabinets and shiny stainless steel appliances have been tastefully placed to add a modern interpretation of tradition of the L-shaped kitchen. From this point of view, the cook can entertain while enjoying a complete view of the porch and Duval Street below.

The master bedroom, with king size bed, is situated just off the back of the living room. Dark mahogany furniture set against cream colored walls and a sky blue ceiling give a West Indies feel to the space. The entire master bath is an art piece in and of itself with rounded counters tiled in mini aqua tiles and a brilliant smattering of sea shells that covers one entire wall and frames the Jacuzzi bath tub. The 'sea shell wall' has become a signature of this owner-artist in her renovation and design work. The precious powder room on the first floor is like a little monument to the islands with a shutter framed mirror, a hand made pedestal counted 'tiled' in sea shells and glass. Even the wash basin in reminiscent of green colored sea glass and an electric photograph of a deserted island takes the decor over the top.

The 2nd bedroom and bathroom are located upstairs just off the hall. Elegant island decor was chosen for this bedroom. White cottage furniture, light wood floors, and a wicker paddle fan are set off with a colorful painting of an inquisitive pelican like the ones we find on the fishing docks all over the Florida Keys. Two twin beds have been arranged in this room so they can be pushed together to make a king size bed.

Starlight Siesta - Secretly situated at the end of a little lane that runs along the right side of the building, this Key West rental features a brand new back lounging deck that nearly spans the width of the building and provides a hidden space for stargazing in the city. The deck connects to a spacious great room which is elegantly furnished with West Indies style linen and woven grass furnishings. As with the front unit, a unique collection of lamps, accessories, and carefully chosen artwork complete this 'picture perfect' great room. In a beautiful contrast to the front unit, soft and relaxing colors were chosen for the back. I love the use of sky blue paint on the ceiling of the great room which helps to bring the outdoors inside. This practice is common for outside porches in Key West and its use inside is inventive and uplifting. The artistic powder room puts the great room over-the-top with rich gold toned walls, designer podium style vanity topped with a clear glass bowl sink, and unique lighting. A metal sculpture of sea creatures frames the vanity mirror creating yet another art space to enjoy.

The elegant kitchen connects flawlessly to the great room via an artistic island dining counter. Tiny sand-stone tiles set in the counter top are artistically placed on the diagonal and offer a refreshing change from overused granite that we see so much of these days. Shiny stainless steel appliances are set off with custom mahogany cabinets, designer lighting, and a grand size gold-framed decorator mirror that is set above the stove.

Both bedrooms with en suite bathrooms are just up the stairs on the 2nd level. The master bedroom, with king size bed, shows an eclectic collection of white wicker and golden bamboo furnishings set against sky blue walls and light hard wood floors. Custom lamps and unique ocean theme art and rugs accessorize the room. The bright white master bath is kept simple and elegant.

The 2nd bedroom and bathroom are also located upstairs just off the hall. Island decor with a nautical theme was chosen for this bedroom that has two twin beds that can be pushed together to make a king size bed. White cottage furniture mixed with rattan, light wood floors, and a wicker paddle fan create and inviting room which is artfully accessorized with a large scale model of a wooden sail boat.

NOTES: In the redesign of this property, all four bedrooms are situated back away from the street to obtain maximum quiet possible. Despite the prime Duval Street location we have noted how quiet the space is whenever we have been inside. You would never guess this gorgeous private Key West rental is here, given its central location in the 700 block of Duval Street. We congratulate the owners on such a remarkable transformation of a historic Key West building to become a spectacular Key West rental. Job well done!

Bedding Summary:

  • Front Unit - Downstairs: 1 King size bed
  • Front Unit - Upstairs: 2 twin size beds (can be made up as a King bed)
  • Back Unit - Upstairs: 1 King size bed, 2 twin size beds (can be made up as a King bed)

Amenities: Wide porch overlooking the 700 block of Duval Street. Large back deck. Brand new artistic renovation. Two fully equipped kitchens, a/c, two washer/dryer units, telephone, and color cable TVs. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.

Parking: Private off - street covered parking for 1 compact car maximum located at the end of the lane underneath the deck. If you arrive by car, please plan to park it in your private parking space and forget about it. Enjoy walking or biking around the island.

Activities: Downtown Old Town Key West on Duval Street in the 700 block. If you are looking for the best place on the island to view the Fantasy Fest Parade - well this is it! Just a few short blocks from Mallory Square, Fausto's Fine Foods for grocery shopping, excellent downtown restaurants, night life, popular clubs, the Historic Seaport, and tropical shops. Sailing, boating, diving, museums.

Restrictions: Smoke free property. Smoking permitted outside only. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. This home is offered as an exclusive vacation rental in the most requested location in Key West.

Area: Walk out your door and down the lane to all you want to see in Historic Key West. Best restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, aquarium, Ship Wreck Museum, Southern Most Point of the U.S., close to beaches. Walk everywhere from here.

Depending on availability - can be rented as 2 Separate Suite Units, "City Island View", and “Starlight Siesta.”

Notes: This is upscale property is ideal for professionals and executives who have discerning tastes looking for a spacious, and luxurious accommodation on Duval Street.

Book Direct For The Best Price Guaranteed

special rates available

Sept 19- Oct 9
Oct 13 - Oct 27
Weekly $2900
Nightly $625

view all specials

Dates Weekly Nightly Terms

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.

  • Front Unit - Downstairs: 1 King size bed
  • Front Unit - Upstairs: 2 twin size beds (can be made up as a King bed)
  • Back Unit - Upstairs: 1 King size bed, 2 twin size beds (can be made up as a King bed)
Sep 15, 2020,
Perfect place!! Excellent view and plenty of space. Small problem with parking but we worked it out. Thanks!!

Mar 20, 2020,
Amazing service, amazing people, amazing place. We felt so welcomed from the moment we stepped onto the property and from all their advice on good food and nightlife we had an unforgettable vacation. Thank you VHKW!

Nov 06, 2019,
Easy check in and check out. Answers all questions promptly.

Aug 10, 2019,
The home was located in the perfect spot on Duval Street. The house itself was great and very clean. Also the sheets on the bed were very soft. The only thing I would say was there could be more lights or different lights in the master bath.

Jun 06, 2019,
This place was perfect for a variety of wedding events! I highly recommend this place. It was more than worth the price!

Dec 18, 2018,
I just returned from two fabulous weeks (12/1-12/15) in Key West celebrating my birthday with friends. We stayed at the Penthouse House on Duval and had both units. What can I say, the property was everything we could have asked for and more....spacious, great location, comfortable beds, plenty of bathrooms. Not to mention a front row seat to all the happenings on Duval, including the Christmas parade. I consider this house a gem. Items to note: If you are a light sleeper, late night music from surrounding bars can be heard in the back bedrooms - it was good music, so it didn't bother me. If stairs are any issue, this might not be the property for you. There is a moderately steep wooden staircase leading up to the property, and all but one bedroom must be accessed via stairs. The stairs leading up to the house can be pretty dark at night. There may have been a switch to an outside light, but couldn't find it. All that being said, I still give it 5 stars. I also have to mention that Paige at KHKW was awesome to work with during the process. She was always pleasant and helpful. I would not hesitate to rent this property or work with the folks at KHKW again.

Nov 29, 2018,
We had a wonderful time! The penthouse was lovely, although, Duval Street is a bit loud sometimes. Your staff made our stay easy. Thank you so much. We will call you again and recommend you to friends.

Nov 07, 2018,
This was our second year to rent this property and Finlay and the entire office team went above and beyond to make our trip fantastic!! Check in and out is super easy and we have already booked again for oct 2019!!

Oct 13, 2018,
Everything in description of property was accurate! Great experience. Just a FYI, as we pulled into parking space when we arrived and got out of my car, a contractor for the property behind the Penthouse on Duval approached us and said, “I can’t believe you assholes pay so much for this property” (in reference to Penthouse on Duval).

Sep 11, 2018,
Extremely pleased with the house!

Aug 29, 2018,
The penthouse on Duval was perfect for our event and we loved the location. It’s a unique house, but we had eight people fit with plenty of room. I would definitely rent again!

Aug 02, 2018,
We enjoyed our stay. There was plenty of space for our party of 11. Parking was a little tight, but we made it work. House was clean and well maintained. I will certainly rent from Vacation Homes of Key West in the future. They were professional and accommodating to my every request.

Jul 21, 2018,
Excellent place. Will book every year.

Jun 24, 2018,
Booking a place through VHKW was easy and they provide great options. They were able to answer any questions beforehand and everything was as described when we got to the rental. Would definitely reccommend them.

Jun 18, 2018,
We loved the Penthouse on Duval! Perfect location and the house itself was great - we had everything we needed and more!

May 07, 2018,
Beautiful home! Easy to reserve, pay and get all the info you need prior to check in and during our stay. Excellent location.

Apr 18, 2018,
The house was beautiful, exactly as pictured. All kitchen utensils you could ever need. I had requested the bedrooms to be made up in king beds, but when I got there some of them weren’t. A quick phone call and it was fixed when we got back from dinner. Great communication. I would definitely stay here or other homes with this company again. Everyone’s favorite feature of this home on Duval St was the dollar bill attatched to some fishing line on the front porch. It made for a lot of entertainment!

Nov 09, 2017,
Perfect location on Duval St plus you get to sit above the street and people watch 24/7.

Aug 30, 2017,
Great place to stay

Aug 22, 2017,
This place is amazing. Great location, lots of room and it's beautiful. We had four couples staying there and there was more than enough space for all of us. We were already talking about booking it again for next year before we even left. The staff was very helpful as well. Also,The off street parking spot was key. I would definitely recommend this place to everyone I know that's planning a trip down. I've stayed in more places in key west than I can count and this one spoiled me.

Jul 26, 2017,
We have always used vacation homes of Key West when visiting our happy place . Unparalleled selection and service. We have never been disappointed!

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









Golf Club Vacation Rentals

key west golf club