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  • (305) 294-7358
Key West Time
June 16th
5:20am · 85°F

Classic Key West Estate ~ Weekly Rental

7BR 5.5BA ~ Weekly Rental
Sleeps 14 - 16

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. Just  a few steps from your front gate, you'll find Date and Thyme Organic Café and Market for delicious healthy treats.

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.

A 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 this 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.  

Bedding Summary

  • First Floor - Bedroom One - 1 Queen Murphy bed; Bedroom Two - 1 King size bed
  • Second Floor - Bedroom Three - 1 King size bed; Bedroom Four - 1 King size bed; Bedroom Five - 1 King size bed; Bedroom 6 - 1 King size bed
  • Pool-side Cottage - 2 full size (double) beds.

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. 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.



Book Direct For The Best Price Guaranteed

special rates available

7BR 5.5BA

June 16 - June 22
June 29 - July 2
July 27 - Aug 3
Nightly $1900
Weekly $10400

view all specials

Dates Weekly Nightly Terms
Jun 10, 2024 - Aug 11, 2024 $11820$1995.005 night min, but 3-4 nights within 60 days
Aug 12, 2024 - Oct 2, 2024 $9190$1950.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $10080$1950.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $17710$3990.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $11820$1995.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $11820$1995.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $9900$1785.004 night min. or 3 night min. 60 days prior to arrival.
Nov 22, 2024 - Nov 30, 2024 $13755$2520.007 night min. or 3 night min. 60 days prior to arrival.
Dec 1, 2024 - Dec 18, 2024 $10395$1950.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $16390$3780.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $18585$4200.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $13020$2835.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $13020$2835.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $13600$2835.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $15490$2835.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $16120$2835.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $15490$2835.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $11820$1995.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $11820$1995.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $11820$1995.005 night min, but 3-4 nights within 60 days
Aug 11, 2025 - Oct 1, 2025 $9190$1950.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $1080$1950.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $17710$3990.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $11820$1995.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $11820$1995.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $10395$1785.004 night min. or 3 night min. 60 days prior to arrival.
Nov 21, 2025 - Nov 29, 2025 $12495$2310.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $10395$1950.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $16860$3885.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $19050$4305.007 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.

Bedding Summary (Main Victorian House):

  • First Floor - Bedroom One - 1 Queen Murphy bed; Bedroom Two - 1 King size bed
  • Second Floor - Bedroom Three - 1 King size bed; Bedroom Four - 1 King size bed; Bedroom Five - 1 King size bed; Bedroom 6 - 1 King size bed.
  • Pool-side Cottage - 2 full size (double) beds.

Floor Plans:

Dec 19, 2023,
The house was great. The location to Duval St. and the docks was even better.

Nov 06, 2023,
The house was wonderful, as was the staff very kind and patient with this extremely ( usually very competent) frazzled widow..

Jan 24, 2023,
The staff at VHKW were great to work with, their communication was excellent, and all instructions were clear and concise. We will absolutely be renting through them again very soon. I highly recommend.

Jun 30, 2022,
Great experience with VHKW. Would definitely book with you guys again.

Jun 07, 2022,
Loved the house and the pool

Apr 20, 2022,
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!

Dec 21, 2021,
Easy to work with!

Oct 07, 2021,
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!!

Jul 22, 2021,
Beautiful old home, nicely updated

Jun 03, 2021,
The home was fantastic. Perfect location. Lots of room to spread out. Great backyard. I would definitely recommend renting this house.Sent by: Teo ( on 3-Jun-21 4:58 PM Opened Hi Troy! Thank you so very much for taking the time to share your amazing experience with us! We appreciate any future referrals and of course would love to host YOU again!  VHKW Team

May 05, 2021,
The house was perfect for our group. Loved the poolside area for gathering, games, and pool 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❤❤

Mar 16, 2021,
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!

Mar 09, 2021,
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!

Feb 24, 2021,
From Start to finish VHKW was helpful in every way imaginable. Would highly recommend staying with them to anyone.

Oct 22, 2020,
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.Sent by: Teo ( on 22-Oct-20 2:11 PM Opened Thank you Laura for your 5 star review. We are so happy that you enjoyed Classic Key West Estate. It sounds like you were having a great time, if the ice maker couldn't keep up with you! :-) Thank you for bringing up the sticky door to our attention, we will make sure our maintenance staff takes care of this. Hot summer days are definitely not the ACs best friend, but guests are always welcome to give us a call and we will help as much as we can to make your stay more comfortable! We look forward to having you back in the near future!   

Sep 08, 2020,
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.

Aug 12, 2020,

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