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  • (305) 294-7358
Key West Time
September 18th
6:49am · 83°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 at once authentic and 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.

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.

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

special rates available

Sept 18- Sept 30
Oct 12- Oct 17
Oct 24- Oct 31
Weekly $6600
Nightly $1400

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Dates Weekly Nightly Terms

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.

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.

May 18, 2018,
We have been coming to Key West for 20 years and this is the first time that we used Vacation Homes. The house was great! The pool was awesome! With 6 couples in one house we thought might be a little crazy but it wasn't. Its big enough that it worked out great. Relaxing in the pool after a night on Duval was just what we needed. We did have a leak that came downstairs in the bathroom. We called and they had someone over to look at it within the hour. Thank You for everything. We will definitely use Vacation Homes again.

Apr 03, 2018,
We really loved this house. The heated pool was amazing. Beds were comfortable. Bathrooms modern and clean. Location was great. Thanks again for another great week.

Nov 11, 2017,
We rented the Classic Key West Estate the first week in Nov. 2017. It was an amazing house!! The main house had 5 bedrooms and the cottage in the back had 1 bedroom that slept 4 people. Plenty of room for our group. The kitchen was huge and very well stocked. The pool was outstanding. We use the pool quite a bit during our stay. The people at Vacation Homes of Key West were very friendly and helpful. Overall it was a great week and we will definitely be back next time.

Nov 11, 2017,
We rented the Classic Key West Estate the first week in Nov. 2017. It was an amazing house!! The main house had 5 bedrooms and the cottage in the back had 1 bedroom that slept 4 people. Plenty of room for our group. The kitchen was huge and very well stocked. The pool was outstanding. We use the pool quite a bit during our stay. The people at Vacation Homes of Key West were very friendly and helpful.

Aug 26, 2017,
The house was perfect for our group of friends. There was plenty of space for everyone. The pool was the best part though. During the summer heat of Key West, we hit the pool every afternoon and just hung out for hours. The house is nicely appointed with all the amenities needed. With the exception of some broken blinds everything was in working order. The location couldn't be any better, just two/three blocks off of Duval. Fantastic place to stay. I would highly recommend it.

Aug 09, 2017,
We had a wonderful week in Key West celebrating my son's wedding. The house was terrific, clean, nice that you supplied paper products and even put out the trash for us to the curb. What a great time and great location. Thanks for all your help and support making this a trip to remember.

Jul 11, 2017,
We were pleased. Very smooth experience. Thank u!

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