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  • (305) 294-7358
Key West Time
January 26th
6:26am · 75°F

Destination Duval - A Premier Key West Penthouse ~ Weekly Rental

4BR 4.5BA ~ Weekly Rental
Sleeps 8

If you’re looking for a perfect Key West vacation rental that’s on Duval St, yet the ideal distance away from the bustle, you’re bound to love our– Destination Duval - A Premier Key West Penthouse. Strategically built on top of Duval Street, up here you’re in the cat bird’s seat, but at the same time invisible to the world below.

Here you can enjoy it both ways – the roominess of a spectacular 4BR 4.5 BA luxury property, above the scenes, yet at the same time in the middle of it all. Who says you can’t have it both ways? Isn’t anything possible in Key West?

Situated in the rooftop residential complex of Duval Square, the original builder innovated this exclusive penthouse for himself. Its avant-garde layout is twice the size of the other residences in the complex and shows off many special design features and decor. This Duval Square vacation rental is beautifully furnished throughout, each room done in soft island colors with modern-minimalist style. Completely hidden from the Key West Island City scene below, your outdoor amenities are kept private for this small rooftop residential complex. Here you’ll enjoy an awesome pool with spacious sun deck and sunshade gazebo.


You’re probably wondering how you get up to Destination Duval - A Premier Key West Penthouse. It’s easily reached by elevator via the secured parking garage reserved for residents only of Duval Square. When you reach the rooftop, the visual transformation is wondrous, it feels more like the ground level of an exotic island courtyard. A synergy of architectural designs, the Mediterranean style gardens have rounded stucco walkways and deep planter boxes filled with tropical plants and palm trees. But the houses are classic Key West conch house design, with clapboard wood siding and deep covered porches that run the width of the buildings. The front door entrance of Destination Duval - A Premier Key West Penthouse is right around the corner from the elevator.


Great Room

Step into the front entrance, and you’re in the kitchen of the captivating multilevel great room. A split-level design elevates the kitchen and dining area two steps above the living room. The sunken living room is grand, running the entire length of the main floor of this penthouse. Spaces are visually interesting and fun to entertain in.

Your eye will immediately be drawn to the two large round windows set up high on the wall towards the peak of the living room roof, adding a hint of maritime flare. Multiple sets of sliding doors on the living room walls bring in the sunlight. When you want to sit outside, they lead to a private roofed porch, that is furnished as a beautiful outdoor living room.

Living Room: Take a turn around the expansive living room area. You immediately feel uplifted with the sensationally high ceiling in the front side of the living room.  All around the living room you see dazzling angles and architectural delights, such as the atrium window and the glass block on walls of the top level. The front side of the living room is set as the main media room with a 50-inch flat-screen TV. Here you can relax and lounge on a comfortable blue linen sofa and loveseat, cushy green and white lounge chair and serve beverages and snacks on the large coffee table.

For more active in-home entertainment at this Duval Square vacation rental, a wooden octagon bumper pool / poker game table is set in the middle of the long living room. The tabletop can also be reversed to set up for dining. Towards the back of the living room, there is second furniture grouping with a full-size sofa and two more cushy chairs of the same design and color found at the front. The back wall is entirely mirrored from floor to ceiling, making the already large room feel even more spacious. High quality artwork, lamps, side tables, and sideboards, are strategically placed around the living room to unify the design and function.

Outdoor Living / Media Room: Besides being able to step outside from the living room, there’s a couple of nice advantages to this outdoor space. First - your own private outdoor lounging room. Second - a 2nd TV, so that you can watch a game and have a movie going on at the same time. This 1st level covered porch is made completely private with lattice walls extending between the porch posts. Nicely decorated with brown wicker chairs and a blue denim sofa, here you’ll enjoy a living room grouping towards the back of the room, and the TV viewing area toward the front.  

Kitchen / Dining Room: Returning inside, the living room area transitions easily to the kitchen via two steps up. The division between the two rooms is also defined by a bright white porch style railing, and the kitchen ceiling is dropped to the usual height. The fully equipped kitchen design is pleasingly understated, with bright white cabinets, matching full-sized appliances and contrasting deep-blue subway tiles. Anyone with a passion for cooking will find everything they need to prepare a nice meal for dining, a long natural wooden farm-style table with eight white wooden chairs is placed in the center of the room, towards the porch style divider railing. An oblong chandelier above the table completes the setting.  

Main Level Bedroom, En-Suite Bathroom, and Half-Bath

Returning toward the front door entrance, a hallway to the left leads to the main level bedroom with en-suite bathroom. It’s architecturally finished with an interesting oblong bay window with recessed lighting, and a modern two blade ceiling fan. Sophisticated and calming, this bedroom suite is decorated in blue and white. It features a light blue accent wall framing a dark wood and wicker headboard for the king size bed. White bedside tables are placed on both sides of the bed.

The en-suite bathroom integrates perfectly with the blue and white bedroom. The pretty dual person shower is finished in glistening light blue subway tiles and a frameless glass shower panel. The oversized white vanity is topped with a white one-piece molded vanity sink and chrome fixtures. A black framed mirror with triple vanity lights completes the elegant look.

This bedroom has a walk-in closet that also serves as the laundry room. Offering a full-size side-by-side front loading washer/dryer, the closet is still large enough to provide plenty of space to hang your clothes and stow a travel bag.

As we leave the bedroom and return to the hallway, there’s one more room to view. A door to the left and opposite the base of the staircase, leads to the bright white half-bathroom, conveniently located steps away from the kitchen. In our slide show, it’s through the door just past the turquoise blue chest of drawers.


Staircase: You really start to feel the special penthouse features of this property when you climb the white helical staircase that leads you up to the top floor. At the top of the circle of stairs, we pause for a moment and take in the interesting angles and views. There’s plenty of light, with spotlights and sky lights overhead, bouncing the light around.

When you reach the landing, notice how the railing widens out and becomes a natural pedestal to display a modern art sculpture. Then, the atrium view. Turn in the opposite direction and check out the atrium window – an angular cut away in the walls so you can look at the main floor below.

The atrium window is unique and gives spectacular perspectives. First, notice the artful perspective of the modern fans hanging from the ceiling. Then move in close to the railing and peek over to get a fun look-down view of the living room below.

Top Level Bedrooms:

What’s on top are the three remaining bedroom suites are on the second level of Destination Duval - A Premier Key West Penthouse. Each suite is unique, offering a tasteful contemporary décor with calming colors, and each provides a private en-suite bathroom. We begin our tour with Bedroom Suite Two, at the top of the stairs.

Bedroom Suite Two: The door for this bedroom suite is immediately to your left at the top of the stairs. A king size platform bed with a smooth wood white frame set against detail rich caning crates an elegant look. In our slide show, this bed is dressed in a pale blue coverlet. Set against an ocean-blue accent wall with casual white-wash bedside tables with white ceramic lamps give the room a sophisticated tropical feel. A large hammered-metal mirror on one wall provides a touch of glamor, and a modern metal ceiling fan ties the look together.

The en-suite bathroom carries the bedroom color theme. Gorgeous ocean-blue subway tiles are set vertically in the shower and finished with a frameless glass shower panel. A white vanity is topped with a bright white molded sink and chrome fixtures. A large frameless mirror mounted over the vanity, is well lit with elegant dual sconce vanity lights.

Bedroom Suite Three: Moving on to the third bedroom, walk straight down the hallway. If you want to reference the photo with the atrium window and the suspended fans, this bedroom is on the right. Soft cream color walls, with a blue accent wall behind the beds, this bedroom provides 2 twin beds. Stylized arched wooden headboards painted cerulean blue are a perfect contrast to the sky-blue wall. In our slide show, the beds are dressed in striped coverlets. A featured art piece of a white coral fan and a metal rutter style ceiling fan add the artistic touches.

The en-suite bathroom carries the blue and white color theme but adds a contrasting gray. The double-size shower is finished with glistening gray subway tiles and a frameless glass shower panel. The vanity base is painted gray to match the tiles and topped with a white molded vanity sink and chrome fixtures. A frameless mirror with triple vanity lights completes the elegant look of the suite.

The Master Suite:

Finally we move to the master suite, the most deluxe bedroom suite in the penthouse. Again, using the photo of the atrium window as a reference point, the door to the master suite is left of atrium window. An enviable feature of the master suite is the private covered outdoor porch. Peek out the bedroom door, and WOW - there's a clawfoot soaking tub on the porch! Just imagine luxuriating in this scene! Talk about wild, and elegantly wonderful, if you’re a bath person, it doesn’t get cooler than this!

Besides the outdoor porch another noteworthy architectural feature is the glass block wall behind the headboard. I love how this retro-tropical touch pays subtle homage to 1980’s Miami Vice tropical décor. This harkens back to when Key West Duval Square was first built and is the perfect back drop for the king size woven grass platform bed, dressed in a tropical print coverlet.

The master bedroom walls are decorated in a subtle cream color that quietly sets off the wood and white bedside tables topped with blue ceramic lamps. The wall opposite the sliding glass door is finished with over-sized mirrors that bounce around the light and make the bedroom feel even larger. On the opposite wall from the foot of the bed, a whitewashed bureau does double duty as the ideal stand for the 40-inch flat screen TV, as well as the place to store clothes. There’s also a comfy green and white easy chair in the corner by the door.

The en-suite master bathroom is a featured room with a spa-like quality and luxury amenities. Soft pale blue and white repeats in this bathroom, but the double-size shower and two-sink vanity top are finished in organic and earth tone colors and textures.

The six-foot long gray granite vanity top provides two under-mounted sinks installed at either end of the counter, providing an abundance of space for your toiletries. Above the granite countertop, a black framed mirror extends the width of the vanity. A set of chrome scone lights are hung over each sink, and double skylights overhead flood in the natural light.  

The inviting double-size shower feels earthy and spa-like. It’s finished with brown ceramic marble tile on the walls, contrasting river rock tumbled marble floor tiles, and a frameless glass splash panel. A head-level window in the shower gives a view of the tropical outdoors.



Swimming Pool / Deck / Gazebo: When you’re ready to head for the pool, turn right out the front door and walk down the garden-lined pathway. At this point it feels a little like walking past Key West conch houses in the sky! In a class all its own, the rooftop grounds really speak for themselves. Poised as a chill-out area above the Duval Street scene, some 3500+ square feet are fitted with an awesome temperature controlled 33’ x 16’ swimming pool, expansive rooftop deck, roofed lanai, and outdoor lounge furnishings. Positioned for birds-eye views of the street scene below, this is tranquil place to sunbath, people watch, and gaze at the moon and stars.

Completely hidden from the Key West Island City scene below, your outdoor amenities are kept private for this small Duval Square residential complex. When you read comments from people who have stayed in this complex, they often comment that they often had the pool to themselves.


Key West Duval Square: Wonderfully convenient when you stay at Destination Duval - A Premier Key West Penthouse, the artfully designed, Duval Square is a vibrant and charming mixed-use complex right on Duval St. It’s generally glossed over in listings for Duval Square vacation rentals. But you’ll find it to be a wonderful convenience and has an interesting history. So here we offer a more detailed description.

On the ground level, Key West Duval Square offers all the conveniences and style of urban penthouse living - security entrances, immediate access to a small courtyard mall with charming shops, and restaurants with secluded courtyard dining. Once you’re settled into the penthouse, it’s convenient to take the elevator into the secured garage with entrances that connect with the ground level shopping and restaurant area.

Built in 1987, it was a ground-breaking concept for Key West – a downsized Euro-style courtyard mall with shops and restaurants below, and rooftop residences above. The design was inspired by the tropical lifestyle and Key West architecture, but it was bit controversial at the time. If you can imagine, the urban land where it’s built was mostly vacant!

Some people objected that it was too urban for laid-back Key West. But today it’s a testimony to forward-thinking architecture and high-quality design that’s stood the test of time. Today, the Duval Square complex preserves and enhances the island village feeling of downtown in the Upper Duval area. On tiny Key West, it’s still remarkable to find an urban mixed-use development that seamlessly blends within the context of the historic neighborhood.

Located in the Upper Duval Neighborhood, it spans the block between Duval and Simonton Streets and runs along Virginia Street. That might sound large, but keep in mind that it takes about 4 Key West blocks to make one New York City block!

The ground level of Duval Square offers a nice mix of quality shops, offices, open-air tropical outdoor gardens, and even a bank. A few quality restaurants have indoor and outdoor seating set among mature tropical landscaping.

You won’t catch a glimpse of this rooftop penthouse when you walk down Duval Street, but it’s a short easy walk home though the Duval Square Mall. Follow an open-air foyer, through a locked gate entrance, and into the covered parking garage. An elevator takes you upstairs from the garage. Of course, if you’re out in your car, simply drive into the secure covered parking lot through the automatic gate on Simonton Street.

Bedding Summary:

  • Main Level (downstairs) – King size bed
  • Top Level (Upstairs) Suite Two – King size bed, Suite Three – 2 Twin size beds, Master Suite – 1 Kind size bed

Amenities: 2,450 SQ FT of interior living space. Private en-suite bathroom for each bedroom. Outdoor covered living room porch on the 1st level, and on the 2nd, level connecting with the master suite. Game table in great room for poker and bumper pool. Fully equipped kitchen, central A/C, and heat throughout. Full-size washer/dryer in laundry closet. Large flat screen TVs in main living room and covered living room porch. Clawfoot bathtub on covered porch connecting with the Master Suite. Expansive 3,300+ SQ FT rooftop deck with tropical landscaping, sun deck, large, covered lanai and lounge furnishings. Security entrances at the ground level to elevator and parking garage. Immediate access to Duval Square below with convenient shopping and restaurants with indoor and outdoor seating. Catering and maid service can be arranged upon request.  

Activities: Walk to all Old Town Key West features and Key West South Beach. No need for a car. Here you’re in the Upper Duval Street neighborhood where you find a wonderful array of excellent restaurants, beautiful boutiques, the Key West Butterfly Conservancy, art and furniture galleries, and the Southernmost Point of the United States. Stroll to nightlife, museums, sailing, boating, snorkeling, diving, theatre, family activities. Right across the street you have Grand Vin Wine Bar, where you’ll enjoy a broad selection of wine by the glass and Flamingo Crossing, the award-winning homemade ice cream store with some of the best ice cream you’ll ever eat. Key West.

Area: Duval Street is perhaps the ultimate tourist street in Key West and certainly the most famous. Nowhere else in the world can you walk a street that connects point-to-point the Atlantic Ocean to the Gulf of Mexico, with a white sandy beach at the south end and Key West Historic Seaport at the north. The Upper Duval Neighborhood Old Town Key West is the more elegant end of Duval Street. Here you find a quieter pace than the bar scene found in the 800 block and 500 block of Duval and below. There are an exceptional variety of outstanding restaurants, wine tasting bar, homemade ice cream, South Beach, boutique shops in the Upper Duval Street Neighborhood. Plus staying Penthouse Duval Square vacation rental, you have immediate access to convenient shopping and courtyard restaurants in the Duval Square Mall with both indoor and outdoor seating.

Parking: Secure gated and covered parking garage with 2 available parking spaces. This is located beneath the Penthouse residential complex.

Restrictions: Subject to all Duval Square Condominium Rules. Smoke free house. This property will accommodate a maximum of 8 persons. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. This property is not licensed for staging an event such as a wedding or large gathering. We would be happy to direct you to facilities that can meet these needs.

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special rates available

Mar 19- Mar 26
April 8 - Apr 17
Weekly $7900

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Dates Weekly Nightly Terms
Jan 22, 2022 - Jan 28, 2022 $6545$1262.255 night minimum - 'within' Sat/Sat Only
Jan 29, 2022 - Feb 18, 2022 $9020$1610.757 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 19, 2022 - Feb 25, 2022 $9710$1664.757 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 26, 2022 - Apr 17, 2022 $8500$1610.757 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 18, 2022 - May 29, 2022 $6510$1162.504 night min. or 3 night min. 60 days prior to arrival.
May 30, 2022 - Jun 10, 2022 $6305$1216.004 night min. or 3 night min. 60 days prior to arrival.
Jun 11, 2022 - Aug 7, 2022 $6900$1232.255 night min, but 3-4 nights within 60 days
Aug 8, 2022 - Sep 30, 2022 $5660$1253.504 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2022 - Oct 20, 2022 $6305$1216.004 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2022 - Oct 30, 2022 $9750$1671.507 night minimum
Oct 31, 2022 - Nov 5, 2022 $6305$1216.004 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2022 - Nov 13, 2022 $6900$1232.257 night minimum
Nov 14, 2022 - Nov 18, 2022 $6305$1216.003 night minimum
Nov 19, 2022 - Nov 26, 2022 $7700$1232.257 night minimum
Nov 27, 2022 - Dec 16, 2022 $5385$1192.504 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2022 - Dec 25, 2022 $8690$1552.007 night minimum
Dec 26, 2022 - Jan 2, 2023 $10300$1975.007 night minimum
Jan 3, 2023 - Jan 13, 2023 $7080$1350.004 night min. or 3 night min. 60 days prior to arrival.
Jan 14, 2023 - Jan 22, 2023 $7480$1350.004 night min. or 3 night min. 60 days prior to arrival.
Jan 23, 2023 - Jan 29, 2023 $7850$1450.005 night minimum - 'within' Sat/Sat Only
Jan 30, 2023 - Feb 11, 2023 $9020$1610.757 night minimum - Sat/Sat Only
Feb 12, 2023 - Feb 18, 2023 $9710$1664.757 night minimum - Sat/Sat Only
Feb 19, 2023 - Apr 8, 2023 $8500$1610.757 night minimum - Sat/Sat Only
Apr 9, 2023 - May 29, 2023 $7080$1300.004 night min. or 3 night min. 60 days prior to arrival.
May 30, 2023 - Jun 10, 2023 $6580$1300.004 night min. or 3 night min. 60 days prior to arrival.
Jun 11, 2023 - Aug 7, 2023 $7150$1300.005 night min, but 3-4 nights within 60 days
Aug 8, 2023 - Sep 30, 2023 $5850$1300.004 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2023 - Oct 20, 2023 $7150$1300.004 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2023 - Oct 30, 2023 $10100$1700.007 night minimum
Oct 31, 2023 - Nov 5, 2023 $6500$1300.004 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2023 - Nov 13, 2023 $7180$1300.007 night minimum
Nov 14, 2023 - Nov 18, 2023 $6500$1300.003 night minimum
Nov 19, 2023 - Nov 27, 2023 $8050$1400.007 night minimum
Nov 28, 2023 - Dec 16, 2023 $5750$1300.004 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2023 - Dec 25, 2023 $9050$1600.007 night minimum
Dec 26, 2023 - Jan 2, 2024 $10500$1750.007 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.

  • Main Level (downstairs) – King size bed
  • Top Level (Upstairs) Suite Two – King size bed, Suite Three – 2 Twin size beds, Master Suite – 1 Kind size bed
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