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  • (305) 294-7358
Key West Time
May 28th
10:01am · 86°F

Designer Octagon House of Key West ~ Monthly Rental

4BR 4BA ~ Monthly Rental
Sleeps 8

Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of Key West, makes a grand architectural statement. Often featured in notable publications with photos of its famous octagon shape front porches, the main structure of the house is in fact rectangular in shape with a multi-sided front. But it is the captivating five-sided front that distinguishes it from the many other remarkable centurion Victorian homes of Key West. Truly a home of fine distinction, it also has an eminent restoration history that began in 1976. Most recently in 2018, it received a sensational interior design makeover that brought it to current 5-Star Quality Resort Amenities standards.


Often referred to as ‘The Calvin Klein House,’ in truth the iconic Designer Octagon House of Key West was an avant-garde preservation project accomplished by designer superstar Angelo Donghia during 1976 – 1978. Because of Donghia’s stellar status in the design world, this single renovation project was transformative for Key West during the 1970’s when creatives were beginning to turn neglected wooden centurion relics into elegant homes.

The recipient of many prestigious awards during his lifetime and posthumously, Angelo Donghia was one of America’s most influential interior and furniture designers during the mid 1960’s through the mid 1980’s, with a celebrity client list with the likes of Ralph Lauren, Neil Simon, Diana Ross, Liza Minnelli, and elite projects such as the Metropolitan Opera House in New York and Omni International Hotels in Miami. His time spent in Miami in the 1970’s peaked his interest in Key West where he could easily escape from the bustle of the city for respite on an island accepting of artistic individuality and alternative lifestyles. “It's a cross between Nantucket and Papeete, in Tahiti. It's not a prissy resort, like Nantucket, but there's some of Nantucket's old elegance mixed with Key West raunchiness.”

“I’m a free spirit and a gambler,” is how Donghia described himself in interview, and when he got to Key West in the 1970’s he was taken with the hundreds of historic wooden houses and craftsmen who were beginning to restore them. When he found the unique octagon house on Eaton Street, it had been standing for over 90 years. Originally built in 1885 by Richard Peacon, the island’s principle grocer at the time, it had fallen into serious decay during economic downturns. As one of his cousins shared with me, Donghia was somewhat reluctant to do the project because of the neglected state of house. But dreamer that he was, in 1976 he purchased it for $45,000, and spent two years restoring it. He turned it into a spectacular show piece putting his indelible signature on the southernmost city.

His approach to the eccentric octagon house had a casual point of view that highlighted renovation and preservation, and the décor reflected his own classic  minimalist design style that earned him the nickname the “man with the gray flannel sofa.” Using tailor’s suiting fabrics, such as canvas, silk, linen and flannel, he ‘dressed’ the rooms much like a tailor. An often-published photo of the living room displays this famous style that would become permanently embraced in the interior design world – white bleached wooden walls and floors, sofa and chairs in simple white canvas coverings, rattan furniture set on a natural fiber rug. Donghia’s renovation project was impeccable to the point where the house sold in 1981 to Calvin Klein for nearly $1 million – 15 times the original purchase and a record price at the time. Today we owe thanks to Angelo Donghia for saving this iconic home while raising the bar on historic home renovation in Key West.  



As you enter the garden gate, the bright turquoise shutters on the house captivate your attention, and your eye is naturally drawn to the center of the octagon porch to find the front entrance. But instead you see a window in the middle, and for a second you might wonder how to get inside. The front door is slightly askance to the right, past the windows at the top of the porch stairs. But before we step inside to take our tour, take a moment to admire the lush tropical gardens, the proportioned five-sided porch details, and matching blue Adirondack rocking chairs that will tempt you to stop here and simply relax into the beauty of the surroundings.

Entrance Hall and Dining Room – When you do step inside, the 12-foot ceilings and tall arches with crown molding are immediately uplifting. Next, notice how the entrance hall features a classic Victorian staircase leading to the 2nd floor, creating a stately ambience. Always an intriguing feature in the grand centurion Key West Victorians, this staircase is elegant, curving out at the bottom – an artisan piece that is beautiful to view in-and-of-itself. Except for the spindles, all woodwork is painted white, in traditional contrast to the bold yellow painted walls of the entrance way.

In the design world, yellow is often used to evoke feelings of happiness, and certainly works here. Dining makes people happy too, and all you need to do is follow the yellow wood walls toward the back of the house and you’re in the vibrant dining room. Here again, classical is contrasted with contemporary with a traditional dark wood dining table and 10 rattan chairs set in the middle of the bright yellow room. A hand-carved teak side table and a pineapple painting offers an exotic touch, while a colorful painting of Ernest Hemingway on one wall, brilliant yellow frangipani flower on another amp up the Key West ambiance of the room.

Donghia once said that … “everything  happened, it seemed, in houses with great moldings,” and as you stand and look around, you’ll see how the thick wooden moldings connect the dining room, living room and the kitchen - one room flowing into the next from the front or the house to the back. Essentially what you experience, is an open concept room, but classical style, with just enough wall space to keep the rooms visually separate.

Living Room – The living room is where we first get to experience the dramatic feel of the octagon space inside the house. A long semi-circular gray-blue sofa centered across the five-sided windows creates a stunning conversation space for family and friends to gather, or even better to just lounge and relax. The mix of the generously proportioned sofa with anvil shape side tables set in bleached wood floors and white pickled walls, beautifully salutes identifiable features of Donghia’s “gray flannel sofa” approach that were used in his famous renovation, and this is wonderful homage to see. A cowhide rug and shag fur stools add a luxurious and imaginative flare to the elegant tailored room.

First Floor Bedroom with En-Suite Bathroom (Bedroom One) – The spacious 1st floor bedroom, has two access points. The main door connects though the wide dining room arch, with double pocket doors and a 2nd door adjoins the living room. Over the arch from the dining room, a shiny lacquered sail fish trophy is boldly displayed on the bright yellow wall. In contrast, inside the bedroom, a quiet décor keeps the same bleached wood floors, white pickled floors and minimalist design found in the living room. Upscale tropical furnishings include a honey-tone king size 4-poster bamboo-wood and wicker bed with matching dresser and side tables, armoire and a sisal rug to add natural texture to the floor. In homage to Donghia’s preservation of the home, an old photograph of the front of the house as it looked when it was restored is hung on a wall.

The en-suite bathroom is in sync with the calming influence of the bedroom. Beautiful bleached bare-wood walls and white tile wainscoting behind the floating white vanity with modern molded square sink create a spa-like feel. A tiled step-in shower closes with a frameless glass door and there is a 4-tiered cabinet for storing your toiletries. Unique gray tone ‘wedding-ring and floral’ porcelain floor tiles create a decadent day-spa feel. Another nice feature is a door that conveniently leads outside to the back covered porch - ideal when you want to throw on your suit and go right out to the swimming pool. You can see the door in our slideshow photo through the mirror above the vanity.

Designer Kitchen – The kitchen adjoins the dining room through a tall wide archway in direct line with the living room. Encompassing the entire back of the house, the kitchen is synonymous with a bold contemporary design in a luxury cooking environment. Unexpected combinations of patterns, colors and textures include spectacular Neolith Calacatta quartz surfaces, and bright white cabinets with window pane tops set in striking contrast to bright red, yellow, and cobalt blue parrot patterned wall paper. Undercounter dimmer lights allow you to set the mood. Two sash windows over the kitchen counter plus two sets of single pane French doors provide multiple views of the expansive wooden deck and lush tropical pool-garden in the back yard.

Then for a prepping for a meal or in-kitchen eating, there’s a large waterfall countertop with a stainless-steel sink with brushed nickel faucets, and a wine fridge underneath. Cobalt blue adds beautiful contrast underneath the island top, where there are four gray wooden chair stools. Throughout the kitchen, floor tiles perfectly match with the quartz countertops.  High-end appliances include a chefs Viking stove with 6 burners, double oven, built-in Bosch microwave, Viking refrigeration with double freezer on the bottom, and touch water dispenser inside the fridge.

Half-Bath off the Kitchen - Before we leave the kitchen to go upstairs, let’s look at the half-bath located off the kitchen at the wall behind the island. Convenient not only from the kitchen, it gives easy access from the back deck just outside the French door. It’s beautifully decorated with Caribbean blue walls, bright white wainscoting, a floating white sink vanity, and unique gray-tone hexagon floor tiles.


Bedroom Two – Returning to the front entrance hall, our tour now goes upstairs to the 2nd floor to view three more bedrooms and two bathrooms. The same vibrant yellow used on the downstairs walls is carried up the staircase and into the 2nd floor hallway. At the top landing, look straight ahead, then to your left to find the entrance to bedroom two. We find more awesome color used in this bedroom, with original pine wood walls painted a striking lavender with white ceilings and trim. Furnished with upscale bright white contemporary colonial furnishings that match the wall trim, this bedroom provides a queen size 4-poster bed with matching headboard and bedside tables. A lacquered bureau with an abstract painting of an octopus on the front, topped with a vase of purple orchids is suggestive of the imaginative style that Donghia introduced, and it’s fun to see this touch added in the current décor. A full-size abstract rug on the wood floor carries on the tropical ocean theme with images of lobsters and coral. Two sash windows look out toward the garden and the 1st floor roof and bring in the sunlight. Finally, for hanging clothes, the original closet is in place.

Bathroom Two (Shared Bathroom) - Directly outside Bedroom Two just a few steps away from the door, is a full bathroom. This bathroom is also shared with Bedroom Four just around the corner at the end of the hallway. Consistent in design with the en-suite bath downstairs, high-end décor creates a spa-like feel. A white modern vanity with molded sink, bare bleached wood walls and ceiling, and floor subway tiles of soft blue, gray, and white. A full-size bathtub and in-tub shower walls are tiled with large faux light gray-white marble bath tiles. A surprise artistic feature is a ships-portal window set in the in the shower wall. From here you have a peek-a-boo view of the garden below.

Now, step back into the hallway and straight ahead at the landing, turn right. Here the hallway leads to the master bedroom with en-suite bathroom, found immediately on the left and Bedroom Four at the end of the hall.

Master Bedroom with En-Suite Bathroom (Bedroom Three) - If you want to sleep in the unique octagon space, make your bid for the master bedroom on the 2nd floor. An exotic black and white scene is created using dark wood furniture with a lathe turned 4-poster King size bed and William and Mary style side tables, set against the bleached bare-wood walls and white trim that remain from Donghia’s timeless restoration. With the dark headboard at the center window, the bed is gently enveloped by the five-sided white trimmed windows. A large armoire holds a 43-inch TV, while an additional open cabinet is available for hanging clothes. An intricate and stunning black and white Indian honeycomb pattern chest placed at the foot of the bed and a faux zebra rug create a chic ambiance and complete the room.

The spectacular en-suite bathroom continues with the black and white monochromatic scheme. Walls done with flat-matt tiles and white paint create a soft and quieting ambiance, and the entire large shower is made of frameless glass making it nearly disappear. Two modern gray-wash floating vanities, with lighted mirrors, are placed on either side of a small-scale French door leading to the 2nd floor verandah. Soft gray-wash floor tiles are perfectly matched with the vanities. Then, as if to belie all the white, every bathroom fixture is mat black,  clearly indicating where to turn on the waters and open and close the shower door. When you’re done showering, put on a nice robe, and you’re in perfect position to walk out the adjoining French door and sit on the porch to enjoy your morning coffee or an evening glass of wine.

Bedroom Four – Situated at the end of the 2nd floor hallway, this bedroom is painted in energetic Caribbean blue with a sand-tone rug, in harmony with colors that Key West is known for. In contrast, walnut tone wooden furniture, including the queen size bed, take a calming South Asian flare lending the room its own exotic feel. Situated at the northeast corner of the house, it is kept bright in the day with four sash windows on two sides of the room.  The original closet is in place for hanging clothes. This bedroom also has the special feature of a private door that leads directly to the 2nd floor verandah overlooking the front and side garden.


Porches and Verandahs -

Key West is known for its alluring gingerbread wrap around verandahs, and this home is famous for its iconic octagon front porches. In the front of the house, the 1st and 2nd floor verandahs offer unique places to relax, enjoy the gardens, and watch the world of Key West go by. On the 1st floor, the verandah wraps around to the east side of the house, joining with a side deck and ultimately a covered porch in the back yard. On the 2nd floor, there are private entrances to the verandah from both the master suite and the northeast bedroom.

In the back of the house, an expansive covered porch adjoins the kitchen through two sets of single-pane French doors on two sides of the house. Set with a sleek built-in banquette along two outdoor walls, the back covered porch is designed as an outdoor lounge or family room. A string hammock is strung on one side of porch when you just want to hang out, and when you’re ready to explore the lush tropical gardens or go to the swimming pool, three sweeping stairs, the length of the porch, unify the back porch with the grand bricked garden.


Back Yard – A phenomenal paradise, the expansive back yard feels like a small private luxury resort with attention to absolutely every detail! Much of it is covered with beautiful brick pathways winding through exotic garden spots planted with a large variety of mature tropical trees, palms, understory, and beautiful flowers. Orchid vines grow on palm tree trunks and one garden spot features a trickling waterfall that spills into a koi pond. An outdoor dining table is perfectly placed in the garden, not far from the back porch.

Beyond the winding brick garden paths, at the back of the property, is a full-size swimming pool surrounded with a large wooden deck. A low brick wall provides a transition between the garden and pool to create two outdoor "rooms." The brick wall features architectural columns that are topped with playful ceramic rooster sculptures.

The poolside area is staged for outdoor recreation with a large wooden pagoda, built along one side of the pool. The inside wall is creatively surfaced with reclaimed wood pieces set in a zig zag design, while a figurehead of Neptune appears to guard from the roof peak. Under the roof, the pagoda is staged with cushy club lounge chairs, a stainless-steel ice maker with two beverage cooler drawers, and a large flat-screen TV. On the other side of the pool, the deck is set with chaise lounges, sun umbrellas, and a full-size ping pong table. Then, at the back of the pool an adorable white cottage with Caribbean blue shutters was transformed into a poolside bathroom with sink and commode. Next to the bathroom cottage, behind a bamboo fence, is an outdoor shower.

Front and Side – Like a story-book picture, a variety of tall palm trees and frangipanis frame the iconic octagon verandahs on the front of the house. A quintessential white picket fence completes the romantic tropical setting in the front garden, while lushly landscaped grounds and privacy fencing continue down both sides of the property all the way around to the back. On the east side of the property, there is a bricked driveway for off-street parking.

Bedding Summary:

  • First Floor (Bedroom One) - 1 King size bed
  • Second Floor – (Bedroom Two) – 1 Queen size bed
  • Second Floor -  (Bedroom Three) Master Bedroom – 1 King size bed
  • Second Floor – (Bedroom Four) -  1 Queen size bed

Amenities: Impeccable renovation with extraordinary designer décor. Expansive exotic back yard resort-style gardens, large swimming pool, outdoor back porch living room, mature tropical landscaping, expansive octagon verandahs, privacy fences. Fully equipped luxury kitchen, central a/c, 43-inch flat screen TV in living room, a 43-inch TV in the master bedroom, and 70-inch TV in the poolside pagoda. Full-size front-loading washer / dryer is set on the covered back porch, tropical style, hidden by a curtain. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.

Activities: Heart of Key West's designated Historic Seaport District. Walk to all old town features, no need for a car. Close to Duval St., close to Mallory Square Sunset Celebration, and a few short streets from Historic Seaport (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Conveniently located to Fausto's Food Palace for gourmet grocery shopping with excellent wine selection, sushi deli, and butcher. Close to shopping, art galleries, and a wide variety of outstanding restaurants and coffee shops. Close to the beach.

Area: This estate home is situated on famous Eaton Street, just one block from the docks of the Key West Historic Seaport. This tiny district is where the founding fathers and mothers built the first shipping docks and warehouses, restaurants and grand homes, including this one. Today these homes stand as one of the largest and most impressive collection of turn-of-the-century architecture in the U.S.A. Today this district includes famous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters, a large variety of historic homes.

Parking: There is a bricked driveway to the left of the house as you face the front. There is room to park more than one car if you park end to end. Once you’re here, park your vehicles and enjoy walking or biking everywhere—you'll see more that way. 

Restrictions: 30-day minimum stay. Ideal for families and groups to unite but is not suitable for staging loud parties. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. Smoke free house. No pets please.

Notes: This property is ideal for professionals, corporate groups, and executives who have discerning tastes looking for a spacious and luxurious accommodation.


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Dates Monthly
May 1, 2024 - May 31, 2024 $24500
Jun 1, 2024 - Jun 30, 2024 $24500
Jul 1, 2024 - Jul 31, 2024 $26500
Aug 1, 2024 - Aug 31, 2024 $22500
Sep 1, 2024 - Sep 30, 2024 $19500
Oct 1, 2024 - Oct 31, 2024 $24500
Nov 1, 2024 - Nov 30, 2024 $25500
Dec 1, 2024 - Dec 31, 2024 $28000
Jan 1, 2025 - Jan 31, 2025 $40500
Feb 1, 2025 - Feb 28, 2025 $42500
Mar 1, 2025 - Mar 31, 2025 $43575
Apr 1, 2025 - Apr 30, 2025 $26000
May 1, 2025 - May 31, 2025 $24000
Jun 1, 2025 - Jun 30, 2025 $24000
Jul 1, 2025 - Jul 31, 2025 $26500
Aug 1, 2025 - Aug 31, 2025 $22500
Sep 1, 2025 - Sep 30, 2025 $19500
Oct 1, 2025 - Oct 31, 2025 $22500
Nov 1, 2025 - Nov 30, 2025 $25500
Dec 1, 2025 - Dec 31, 2025 $28000

Additional Notes:

  • 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.
  • Future Dates not listed, please call 305-294-7358 for pricing.

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.

  • First Floor (Bedroom One) - 1 King size bed
  • Second Floor – (Bedroom Two) – 1 Queen size bed
  • Second Floor -  (Bedroom Three) Master Bedroom – 1 King size bed
  • Second Floor – (Bedroom Four) -  1 Queen size bed
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