Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once historic and exotic. If you've ever had the opportunity to stroll the residential streets of the famous Key West Historic Seaport neighborhood, you have experienced first-hand the type of incredible architectural history embodied in this authentic turn of the 19th Century property. The location of this estate property is where you'll find some of the most iconic destinations on the island.
When your group gets ready to go out together to eat, drink, and listen to music, there is absolutely no need for a car. It's a 3-minute walk to the docks of the Key West Historic Seaport., and there's an abundance of options to choose from. Experience some of the most famous eateries and bars on the island. Book a sunset cruise or fishing charter. Start the morning at the Cuban Coffee Queen or Pepe's Cafe - one of the oldest seaport restaurants on the island. Indulge in fresh oysters at the Half Shell Raw Bar; listen to live music and admire the old wooden sail boats at the Schooner Wharf Bar. Dine together at the Conch Republic Seafood Restaurant or grab an infamous fish sandwich at BO's Fish Wagon.
Displaying an abundance of elegant Victorian design, artisan ship carpenters milled elaborate gingerbread trim that the front of the 7 BR 5.5 BA Classic Key West Estate home. Deep porches with turned columns grace the entire width of the first and second floor porches. Beautiful stained glass transom windows top symmetrically set French doors. Oversized windows surround the home to invite in the light and tropical breezes. A beautiful pool-side pied-a-terre, in the private back yard, provides the perfect touch of fantasy. The quintessential white picket fence with capital topped posts gracefully surrounds the front yard to complete the perfect picture of opulence.
Interior Layout: Throughout the years, the interior of this home has mostly, retained its original layout. Many of the walls in the house feature the revered heart pinewood planks used to build this home in the late 1800’s. During renovations in the 1970’s, much of this long extinct pinewood, was meticulously hand-sanded by craftsman to reveal its natural warm glow.
Throughout the Classic Key West Estate, the historic rooms are furnished and decorated with up-scale tropical furniture and pleasing artwork. Featured on one living room wall, is a commissioned historiography art piece that depicts the timeline of this estate. It was researched and created by local professional historian Sharon Wells.
At vacation stay in this elegant home harkens back to the time when seafaring merchants and traders were first settling the island. The owner of the home continues to make thoughtful upgrades to this vintage property to constantly improve the unique vacation rental experience is offers.
A classic 1800’s Federal style center-hall makes an impressive entrance statement. Step inside and the wide 1st floor hallway leads to the back of the house. Stately rooms with 12- foot ceilings line both sides of the house. The wooden banister staircase was intricately carved by early artisans. It provides the visual center point of the first floor.
Right side (facing the front of the house): On the front right side of the staircase is the spacious living / media room. It is nicely furnished in light tropical colors with traditional wood and wicker furnishings. A 50-inch TV provides the focal point for shared media entertainment.
The living / media room is open to the dining room via an expansive wooden archway. The dining room is nicely staged for group dining. A single door at the back wall of the dining room leads to the upscale kitchen.
The kitchen was stylishly renovated with luxury upgrades. Walls are painted a dramatic blue, in striking contrast with the bright white cabinets, stainless steel appliances, and earth tone granite counter tops.
The kitchen is located at the back of the house. This is ideal for enjoying the indoor / outdoor Key West lifestyle. Two sets of French doors, at the back corner of the kitchen, lead to the pool and deck area.
Left side (facing the front of the house):
Bedroom One: Returning to the front of the house, the first room on the left is bedroom one. Nicely decorated to double as an office / den, it has a Murphy bed on one wall. The bed makes up as a comfortable queen size bed.
Bedroom Two: Walking toward the back of the house, the next door on the left is bedroom two. This bedroom is authentically furnished and includes a metal king-size bed, and an antique wooden dresser and armoire. This bedroom also provides an en-suite bathroom.
In contrast with the bedroom, the en-suite bathroom is a modernistic design. It is decorated in white and fitted with a double wooden vanity topped with chic composite countertops. The shower is oversized with frameless glass doors. Contrasting black bathroom fixtures add elegance to the room.
Back out to the hallway, the last room on the downstairs left is a half-bath with a sink, commode, and mirror. Conveniently located near the back yard pool it serves as the pool bath.
Backyard of the house:
Pool and Deck: The most direct path to reach the back yard and swimming pool, is through the kitchen. At the back corn wall of the kitchen double sets of French doors open to the deck.
The backyard deck is set up as an outdoor lounging and dining area. A dining table with chairs are placed under a covered porch. An awning extension adds protection from the rain. The outdoor dining table is positioned near the kitchen making it easy to serve and entertain outside. For poolside media enjoyment, a flat screen TV is placed on the exterior wall above the table.
Studio Cottage – Bedroom Three: A bonus feature of this estate property is the upscale free-standing studio cottage, with a full bathroom and kitchenette. It provides two full-size (double) beds that are positioned to catch a view of the pool.
Situated across the back deck from the main house, it offers privacy from the main house. Décor is elegant with pinewood walls and open-beamed ceilings.
Returning to the front of the house, we ascend the banister staircase to the 2nd floor. The landing leads to an impressive and dramatic hallway.
At the front and back of the 2nd floor, exterior doors lead to covered porches. The front door connects with the 2nd floor covered front porch, that spans the width of the house. From up here enjoy a view of beautiful Fleming Street below.
At the back of the house, a door leads to the upstairs covered back porch. From here enjoy a view of the neighborhood rooftops and the pool-garden below.
There four bedrooms and two bathrooms upstairs. All four bedrooms are spacious and feature 10+ foot ceilings. Each upstairs bedroom is uniquely decorated yet integrated in design with the other bedrooms. All four bedrooms provide a king size bed, dresser, bedside tables, and reading lamps.
Upstairs Right side (facing the front of the house):
The right side of the upstairs has two spacious bedrooms and one bathroom. During an early renovation, Key West craftsmen meticulously restored the original pinewood walls on the upstairs right side of the house. The warm hand-rubbed wood honors the historic authenticity of the house.
Bedroom Four: Apart from the beauty of the wood walls and high ceilings, bedroom four has windows on two walls that invite in the natural light. The fourth bedroom offers a king-size. It also has a nice view of the covered front porch.
Bedroom Five (with en-suite bathroom): The fifth bedroom five is the next room down. It can be accessed from the hallway, or through double French doors which connect to bedroom four. You may have to flip a coin to see who gets bedroom five. Bedroom five is prominently furnished with a dark-wood canopy king-size bed and features a beautiful historic en-suite spa-bathroom.
En-suite Spa Bathroom: The Colonial-Caribbean design of this special spa bathroom creates an aire of island romance. A soaring ceiling adds to the spacious feeling and adds a dramatic flair. There is an oversize shower in one corner. A double white wood vanity sink is topped with a large antique mirror that bounces around the light. An upholstered chaise, set against the bare wood walls, give this special bathroom an exotic feel.
Upstairs Left side (facing the front of the house):
In elegant contrast to the bare wood walls on the right side of the upstairs, all bedroom walls on the left side are painted a soft yellow. Painted antique planks create a light backdrop to show off dark wood and wicker beds and pleasing artwork.
Bedroom Six: Returning to the front of the house, bedroom six is in the upstairs left corner. As a corner bedroom, there are two exterior walls with four large sash windows that invite in the sunlight. Bedroom six provides a king-size bed.
Bedroom Seven (with en-suite bathroom): Back to the hall and past the stairs, bedroom seven is the next in line. also provides a king-size bed. While there is only one exterior wall in bedroom seven, oversized windows assure plenty of natural light. Bedroom seven connects with a full en-suite bathroom, with a second door that leads to the hallway.
Second Upstairs Bathroom: The last room at the end hallway, on the left, is a full bathroom with shower. Bedroom four and six, at the front of the house, share this bathroom.
Grounds: The property grounds are fenced in the front and back for privacy. The back yard is decked creating a wonderful place for private entertaining complete with swimming pool, and an upstairs verandah creates a covered loggia. Beautiful palm trees and foliage create a romantic tropical setting. The front of the home has beautiful curb appeal with large front porches on the first and second floor that overlook the estate neighborhood.
Note: If your group grows, or if you just want more room to spread out, rent th is home with a private Caribbean Guest House. The combination of the two houses is available to rent as the 10 BR 7.5 BA Old Town Caribbean Estate.
Amenities: Upscale renovations and antique and furnishings. Swimming pool, large deck, tropical gardens, expansive porches, and privacy fences. Fully equipped kitchen, central a/c, telephone, cable TV, stereo, washer / dryer. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled. Complimentary parking pass for City Parking Garage.
Activities: Heart of Key West's designated Historic Seaport District. Walk to all old town features, no need for a car. Just 3 1/2 streets to Duval St., close to Key West Mallory Square Sunset Celebration, and a few short streets from Historic Seaport and retailers (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 gourmet grocery shopping with excellent wine selection, sushi deli, and butcher. Close to shopping, art galleries, and a variety of national and international restaurants, coffee shops. Close to the beach.
Area: This estate home is situated on famous Fleming Street in the Historic Seaport Neighborhood. This part of the island is on the gulf side and encompasses the original lower Duval Street area. This tiny district is where the founding fathers and mothers of the late 1800's 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. Today this district includes famous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters, a large variety of historic homes, and Mallory Square.
Restrictions: While this property is ideal for families and groups to unite, is not suitable for staging loud parties. Smoking permitted outside only. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
May 21- May 26
May 31 - June 7
|Apr 18, 2022 - May 29, 2022||$10950||$1950.00||4 night min. or 3 night min. 60 days prior to arrival.|
|May 30, 2022 - Jun 10, 2022||$9650||$1860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jun 11, 2022 - Aug 7, 2022||$10950||$1950.00||5 night min, but 3-4 nights within 60 days|
|Aug 8, 2022 - Sep 30, 2022||$8750||$1860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Oct 1, 2022 - Oct 20, 2022||$9600||$1860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Oct 21, 2022 - Oct 30, 2022||$20100||$3450.00||7 night minimum|
|Oct 31, 2022 - Nov 5, 2022||$9600||$1860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Nov 6, 2022 - Nov 13, 2022||$11400||$1950.00||7 night minimum|
|Nov 14, 2022 - Nov 18, 2022||$9600||$1860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Nov 19, 2022 - Nov 26, 2022||$12500||$2000.00||7 night minimum|
|Nov 27, 2022 - Dec 16, 2022||$8760||$1860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Dec 17, 2022 - Dec 25, 2022||$14380||$3380.00||7 night minimum|
|Dec 26, 2022 - Jan 2, 2023||$16540||$3675.00||7 night minimum|
|Jan 3, 2023 - Jan 13, 2023||$11330||$2860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jan 14, 2023 - Jan 22, 2023||$11330||$2860.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jan 23, 2023 - Jan 29, 2023||$11910||$3000.00||5 night min, but 3-4 nights within 60 days|
|Jan 30, 2023 - Feb 18, 2023||$13590||$3000.00||5 night min, but 3-4 nights within 60 days|
|Feb 19, 2023 - Feb 25, 2023||$14150||$3000.00||5 night min, but 3-4 nights within 60 days|
|Feb 26, 2023 - Apr 8, 2023||$13590||$3000.00||5 night min, but 3-4 nights within 60 days|
|Apr 9, 2023 - May 29, 2023||$14820||$2640.00||4 night min. or 3 night min. 60 days prior to arrival.|
|May 30, 2023 - Jun 10, 2023||$11260||$2540.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Jun 11, 2023 - Aug 7, 2023||$9900||$2640.00||5 night min, but 3-4 nights within 60 days|
|Aug 8, 2023 - Sep 30, 2023||$11260||$2640.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Oct 1, 2023 - Oct 20, 2023||$9900||$2640.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Oct 21, 2023 - Oct 30, 2023||$14490||$3550.00||7 night minimum|
|Oct 31, 2023 - Nov 5, 2023||$9910||$2500.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Nov 6, 2023 - Nov 13, 2023||$11930||$2800.00||7 night minimum|
|Nov 14, 2023 - Nov 18, 2023||$9910||$2500.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Nov 19, 2023 - Nov 27, 2023||$13100||$3200.00||7 night minimum|
|Nov 28, 2023 - Dec 16, 2023||$9100||$2650.00||4 night min. or 3 night min. 60 days prior to arrival.|
|Dec 17, 2023 - Dec 25, 2023||$14810||$3450.00||7 night minimum|
|Dec 26, 2023 - Jan 2, 2024||$16870||$3800.00||7 night minimum|
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 - firstname.lastname@example.org
VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.
Bedding Summary (Main Victorian House):
“The compound was amazing! It was perfect for our group and the houses were really nicely renovated and decorated. I hope to be able to stay there again someday!
“Easy to work with!
“Perfect location right outside of town but in walking distance to everything. The house is full of charm and character. Perfect size for a large group. We had plenty of room and the accommodations were clean and comfortable. We are all hoping to stay again soon!!
“Beautiful old home, nicely updated
“The home was fantastic. Perfect location. Lots of room to spread out. Great backyard. I would definitely recommend renting this house.
“The house was perfect for our group. Loved the poolside area for gathering, games, and pool time...so private and quiet. The rooms were spacious and remarkably quiet between them. We loved the location. Walking distance to everywhere. Great neighborhood restaurants, we loved FreshCo and Thirsty Mermaid. Parking was the biggest issue and we ended up finding street parking and tried not to drive much. We loved our stay and would stay again❤❤
“Cool historic home in a great location. It had all the space and everything we needed for our family and friends. Walkable to all Key West has to offer. We would definitely stay again. Thank you so much!
“Check-in and check-out procedures were very easy to follow. We had a few occasions to call for assistance, and the issues we had were addressed immediately. The house we rented was very clean when we arrived. Nothing to do but unpack and enjoy our vacation home!
“From Start to finish VHKW was helpful in every way imaginable. Would highly recommend staying with them to anyone.
“We thoroughly enjoyed our recent stay. The historic home is a beautifully landscaped and decorated property. We especially enjoyed the pool area and the verandas. The only negatives are the ice maker couldn’t keep up with us :-) and air conditioning struggled to cool large home in 95 degree weather. One of the three back doors was sticking, so we didn’t use it. All in all this was a wonderful property.
“Loved the house! It was such a neat place with such history. I would have liked a heads up that there was a nude men's resort next door that would be visable from the windows on the right side of the house before opening the blinds as the house is a little dark. Was not prepared for that and i would not recommend it for anyone staying there with children, but for our group of adults it made for an interesting first impression.
“House was great as well as the customer service from VHKW. Wish we had found you before making our initial reservation through VRBO! Looking forward to our next visit.
“We had a fantastic trip to Key West and the Classic Key West Estate was great for our large group. We didn't have any issues with the house and VHKW was very accommodating and great to work with. Thank you!
“What a fantastic experience! We rented the Classic Key West estate in order to have family close for our wedding. The house had enough space for everyone, and the pool house offered the perfect private space for my fiance and I. The house had more than we expected, was extremely well stocked, and the staff was incredibly helpful when we needed it. Would give it 6 stars if we could - thank you VHKW, for helping make our wedding a perfect experience!
“The staff was easy to deal with and straight forward. The house was ready on time. There was an issue with internet that ended up being with the provider, maintenance took care of contacting them and relaying repair info to us. Problem was resolved quickly. We thoroughly enjoyed our stay and would absolutely stay there again if we had a large number of people.
“Love this house. Very clean, well-maintained home. Walking distance to Duvall Street and Marina
“The house was perfect!! We had 12 guys and never felt cramped. Easy walk to the marina and Duval st. The renting process was simple and straight forward. We would rent this home again in the future. Thanks
“Beautiful home with all the bells and whistles for a large group. Beautifully remodeled and decorated with lovely housewares, sheets and towels. The property is across the street from an organic market and coffee shop which offers divers breakfast and lunch options as well as being centrally located to key locations on the island! Definitely a re-do and kudos to VHKW!!!
“We had 13 hours family members for a week-long vacation in Key West ranging in age from 11 to 70. The house met all of our needs, and was comfortable for everyone! The kitchen is well appointed and the pool area a very relaxing place for us to gather. We especially appreciate Paige making a trip to successfully locate and return items we left behind!
“This house accommodated our large group. Kitchen well equipped. Great location. When we had an issue with a shower head, maintenance came right away to fix it. When a storm came thru, pool maintenance came when we called to clean the pool. Seamless process with reservations, payment, and confirmation. Thanks VHKW!
“GREAT HOME WITH A GREAT LOCATION. VHKW WAS VERY ACCOMMODATING
“Classic Key West Estate was everything we had hoped for. We celebrated our 40th wedding anniversary and renewed our vows on Smathers Beach while we were there. The home was a great place to stay with family and friends! A wonderful time was had by all. The home is clean and very spacious. The kitchen had everything we needed. The bedrooms are enormous and the beds are very comfortable. The bathrooms are large and well updated. The only negative would be that the chairs in the living room and front porch are in desperate need of repair and new cushions would make things perfect. But, we spent the majority of our time outside on the pool deck and patio. That area is perfect for meals and relaxation. The covered area is perfect for getting out of the sun. We would definitely recommend and rent this property again!
“Great property and service. We had a wonderful time.
“Great service thanks for a great vacation
* This property may not be available for the dates above due to other inquires and pending reservation.