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  • (305) 294-7358
Key West Time
October 22nd
9:28pm · 79°F

Classic Key West Estate ~ Weekly Rental

7BR 5.5BA ~ Weekly Rental
Sleeps 12-14

Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have experienced first hand the type of incredible architectural history this authentic classic revival mansion embodies. This is a grand wooden Key West historic home that was built in the late 1800's most probably for a prominent seafaring captain.It is one of the few Key West estates for rent as a licensed weekly vacation rental.

Displaying an abundance of elegant and gracious Victorian design, artisan ship carpenters milled elaborate gingerbread trim that adorn turned porch columns that line the front of the Classic Key West Estate home. Deep porches grace the entire width of the first and second floor porches, beautiful stained glass transom windows top symmetrically set French doors, and 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 capitals topped posts gracefully surrounds the front yard to complete the perfect picture of elegance. If you're looking at Key West estates to rent for a larger group, this could be the perfect match for you.

Interior Layout: Throughout the restorations and renovations the interior of this home has, for the most part, retained its authentic original layout. Below is detailed description by floor. 

Downstairs - Right side (as you face the house): A classic center hall design lends for the impressive hard wood entrance hall that leads all the way to the back of the house. The original wide wooden banister staircase is intricately carved, and anchors the center point of the home. Stately rooms with 12- foot ceilings line both sides of the house.

The front right side of the first floor holds a spacious living / media room that gently flows via a mid-point archway into the large dining room ideally staged for group dining. These rooms are beautifully furnished and artfully decorated with up-scale tropical furniture, and pleasing art work. The last room on the right is the beautifully renovated kitchen.

Complete with granite counter tops, and cook's island, this luxurious kitchen has French doors that lead to the pool and deck area on one side and a doorway to the dining room on the other. The layout is ideal for entertaining.

Downstairs - Left side (as you face the house): Across the center hall are the rooms that line the left side of the house. The front room on the left is the perfectly appointed study. Furnished with comfortable seating, a writing desk, and a wall of bookshelves, this beautiful has the added feature of a delightful Murphy bed that makes this room a delightful sixth bedroom in the home.

Go out the door from the library and turn left down the hall, and the next door is the second downstairs bedroom. This room bedroom has a king sized bed. Authentic and romantic appointments include antique armoire, and beautiful art work. This bedroom is completed with an en-suite bathroom. The last room on the left is a half bathroom.

Outside in the back is the private swimming pool and wooden pool deck. An outdoor dining table is positioned near the kitchen doorway. There is plenty of seating for sunning and lounging.

Pool Side- in the back: The pool-side pied-a-terre in the private back yard provides the perfect touch of fantasy. Enter this wooden cottage with shiny tin roof through a double set of sliding French doors just off the pool deck. Inside you will find beautiful bare pine wood walls and open beam ceilings. This romantic space provides its own kitchenette and a full bathroom. There are two full (double) size beds each placed to catch a view of the pool.

Upstairs - Right side: The beautiful banister staircase goes straight up and leads you to the back of the second floor. Atrium style hallways switch back on both sides of the stairway to create the entrances for the four bedrooms. From the right front of the house looking back, the first room we call Anne's room. This styled room has a king size bed, dressed in beautiful bed coverings. Exposed, hand rubbed bare heart pine walls and romantic window sheers create a wonderful joyful feeling. The second room to the right also offers a king size and it is completed with a large en-suite bath. This bathroom features a double sink vanity, shower and a chaise lounge chair.

Upstairs - Left side: The left front bedroom on the second floor we call Jack's room. This spacious handsome room is fit for anyone with discerning taste. Like all the other luxury bedrooms in this great home, it feels grand and inviting. Jack's room has a comfortable wood and wicker king size bed, halo netting, artistic furnishings. Pale yellow walls with crown molding offset the beautiful heart pine wooden floors. The next room down the left side is comprised of a large beautifully furnished bedroom and spacious en-suite bathroom, these beautiful rooms are comforting and a joy to be in. The bedroom offers the same style king size wood and wicker bed we find in Jack's room. Other appointments include artful furnishings including French country style armoire. Like the front left hand bedroom, walls are painted a subtle tropical yellow that warmly highlights the heart pine floors. Crown molding and ginger bread trim around the windows and doors add the final touch to make this suite picture perfect.

The last room off the hall is the third bath on the second floor. This is a full bath and serves as the bathroom for Anne and Jack's rooms.

Exterior Layout:

Upstairs - Porch and Verandah: At the very end for the hall in the front is a door that goes to the deep porch that runs the full length of the house, a perfect place to watch the world go by.

Back Verandah - At the very end of the hall in the back is a door that goes to a verandah that runs the full length of the house. The verandah overlooks the deck and the pool.

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.

Bedding Summary:

  • First Floor - 1 king size bed, 1 Queen Murphy bed, 1 queen sleeper sofa.
  • Second Floor - 4 king size beds
  • Pool-side Cottage - 2 full size (double) beds.

Amenities: Upscale renovation and antique 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 KeyWest 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 disctrict 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.

Notes: This property is ideal for professionals and executives who have discerning tastes looking for a spacious and luxurious accommodation that is truly authentic.

Today there are only a few such historic estate homes that are available for rent as private, single-family residences. Most homes of this type have been made over into apartments or bed and breakfast accommodations.

Book Direct For The Best Price Guaranteed

Dates Weekly Nightly Terms
Oct 22, 2021 - Oct 31, 2021 $12655$2169.507 night minimum
Nov 1, 2021 - Nov 6, 2021 $8055$1553.504 night min. or 3 night min. 60 days prior to arrival.
Nov 7, 2021 - Nov 14, 2021 $9500$1696.507 night minimum
Nov 15, 2021 - Nov 19, 2021 $8055$1553.504 night min. or 3 night min. 60 days prior to arrival.
Nov 20, 2021 - Nov 28, 2021 $9130$1630.507 night minimum
Nov 29, 2021 - Dec 17, 2021 $7310$1618.754 night min. or 3 night min. 60 days prior to arrival.
Dec 18, 2021 - Dec 25, 2021 $11910$2127.007 night minimum
Dec 26, 2021 - Jan 2, 2022 $13580$2328.007 night minimum
Jan 3, 2022 - Jan 14, 2022 $10595$2119.004 night min. or 3 night min. 60 days prior to arrival.
Jan 15, 2022 - Jan 21, 2022 $10595$2043.504 night min. or 3 night min. 60 days prior to arrival.
Jan 22, 2022 - Jan 28, 2022 $11110$2142.755 night minimum - 'within' Sat/Sat Only
Jan 29, 2022 - Feb 18, 2022 $15810$2823.257 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 19, 2022 - Feb 25, 2022 $16500$2828.757 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 26, 2022 - Apr 17, 2022 $15810$2823.257 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 18, 2022 - May 29, 2022 $11570$2066.254 night min. or 3 night min. 60 days prior to arrival.
May 30, 2022 - Jun 10, 2022 $10815$2085.754 night min. or 3 night min. 60 days prior to arrival.
Jun 11, 2022 - Aug 7, 2022 $12265$2190.255 night min, but 3-4 nights within 60 days
Aug 8, 2022 - Sep 30, 2022 $9820$2174.504 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2022 - Oct 20, 2022 $10815$2085.754 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2022 - Oct 30, 2022 $16985$2911.757 night minimum
Oct 31, 2022 - Nov 5, 2022 $10815$2085.754 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2022 - Nov 13, 2022 $12760$2278.757 night minimum
Nov 14, 2022 - Nov 18, 2022 $10815$2085.754 night min. or 3 night min. 60 days prior to arrival.
Nov 19, 2022 - Nov 26, 2022 $12265$2190.257 night minimum
Nov 27, 2022 - Dec 16, 2022 $9820$2174.504 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2022 - Dec 25, 2022 $15995$2856.257 night minimum
Dec 26, 2022 - Jan 2, 2023 $22795$3907.757 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.

  • First Floor - 1 king size bed, 1 Queen Murphy bed, 1 queen sleeper sofa.
  • Second Floor - 4 king size beds
  • Pool-side Cottage - 2 full size (double) beds.

You can also view a detailed floor plan of the property here and detailed floor plan of the 1st & 2nd floor bedroom layout here.

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.

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.

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,

Mar 17, 2020,
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.

Feb 19, 2020,
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!

Nov 27, 2019,
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!

Nov 10, 2019,
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.

Oct 17, 2019,
Love this house. Very clean, well-maintained home. Walking distance to Duvall Street and Marina

Oct 01, 2019,
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

Sep 01, 2019,
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!!!

Jul 19, 2019,
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!

Jul 04, 2019,
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!

Jun 11, 2019,

May 03, 2019,
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!

Jan 23, 2019,
Great property and service. We had a wonderful time.

Jan 12, 2019,
Great service thanks for a great vacation

Nov 26, 2018,
Awesome house and amenities! Cozy and relaxing furnishings as well. The best part is the location. Not too far from Duval to stroll but enough distance for when you want to remove yourself from the scene.

Oct 06, 2018,
Could not have asked for a better setting to host several couples for a relaxing and fun long weekend. Literally nothing negative to say about the property, people or process for staying here. This is one of the few places where the pictures do not exaggerate the quality of the property, if anything it was better than the photos. Thanks again for an easy rental process and a great stay.

Sep 09, 2018,
Great location and a very beautiful house. The neighborhood was very nice as well. I would recommend this home to anyone.

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