Classic Key West Estate ~ Weekly Rental

7BR 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 modern 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 large room bedroom has a king sized bed. Authentic and romantic appointments include mosquito netting, antique armoire, and beautiful art work. The last room on the left is a full 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: A newly renovated 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 new 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.

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 left back bedroom, known as 'the guest room' also provides a king size bed.

The next rooms down the left side are the Executive Suite. 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 an upholstered dressing bench and 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: Front Porch 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 luxury furnishings. Swimming pool, large deck, tropical gardens, expansive porches, and privacy fences. Fully equipped kitchen, central a/c, telephone, color cable TV, stereo, washer / dryer. 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. 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.

  • 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.
Dates Weekly Nightly Terms
Feb 27, 2016 - Apr 15, 2016 $8700$16007 night minimum
Apr 16, 2016 - Aug 12, 2016 $6800$13007 night min. or 3 night min. 60 days prior to arrival.
Aug 13, 2016 - Oct 22, 2016 $6350$12503 night minimum
Oct 23, 2016 - Oct 29, 2016 $9700$18007 night minimum
Oct 30, 2016 - Nov 6, 2016 $6350$12503 night minimum
Nov 7, 2016 - Nov 13, 2016 $7300$13007 night minimum
Nov 14, 2016 - Nov 18, 2016 $6350$12503 night minimum
Nov 19, 2016 - Nov 25, 2016 $7300$13007 night minimum
Nov 26, 2016 - Dec 17, 2016 $5400$12503 night minimum
Dec 18, 2016 - Dec 25, 2016 $8700$16007 night minimum
Dec 26, 2016 - Jan 1, 2017 $10440$20007 night minimum
Jan 2, 2017 - Jan 13, 2017 $7100$16007 night minimum
Jan 14, 2017 - Jan 20, 2017 $9900$18007 night minimum
Jan 21, 2017 - Jan 27, 2017 $7500$16007 night minimum - Sat/Sat Only
Jan 28, 2017 - Feb 3, 2017 $7800$16007 night minimum - Sat/Sat Only
Feb 4, 2017 - Feb 17, 2017 $8700$16007 night minimum - Sat/Sat Only
Feb 18, 2017 - Feb 24, 2017 $9200$16007 night minimum - Sat/Sat Only
Feb 25, 2017 - Apr 21, 2017 $8700$16007 night minimum - Sat/Sat Only
Apr 22, 2017 - May 29, 2017 $7300$13004 night min. or 3 night min. 60 days prior to arrival.
May 30, 2017 - Jun 16, 2017 $6350$12504 night min. or 3 night min. 60 days prior to arrival.
Jun 17, 2017 - Aug 11, 2017 $7300$13007 night min. or 3 night min. 60 days prior to arrival.
Aug 12, 2017 - Oct 21, 2017 $6350$12503 night minimum
Oct 22, 2017 - Oct 28, 2017 $9700$18007 night minimum
Oct 29, 2017 - Nov 5, 2017 $6350$12503 night minimum
Nov 6, 2017 - Nov 12, 2017 $7300$13007 night minimum
Nov 13, 2017 - Nov 17, 2017 $6350$12503 night minimum
Nov 18, 2017 - Nov 24, 2017 $7300$13007 night minimum
Nov 25, 2017 - Dec 16, 2017 $5400$12503 night minimum
Dec 17, 2017 - Dec 25, 2017 $8700$16007 night minimum
Dec 26, 2017 - Jan 1, 2018 $11000$20007 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, New Years, Key West Yacht Race Week, Thanksgiving, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, Biker's Poker Run, 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 - info@vhkw.com

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