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Book Online or call HomeAway Booking Assistance 888-640-7927
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Grande Dame Key West ~ This award winning renovation of a 3 - story Estate

Bedrooms 7
Space 5,047 sq ft
Property type house
Minimum Stay 4 - 7 nights


About the property

Estate, 7 Bedrooms + Other (See Description), 7 Baths, (Sleeps 14-16)

Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and modern convenience, making this property both aesthetically alluring and delightfully comfortable.

Originally built by the Watson Family in the 1840's, this mansion has kept the Watson name as homage to the original owners Susan and William Watson. Today this home is one of the most beautiful and unique licensed vacation homes of this size and stature on our island. It is the perfect place for the family or small corporate group with discerning tastes. Located right in the heart of Old Town Key West's historic section of beautifully restored 19th century mansion homes, this vacation rental is situated in the 500 block of Simonton Street, just steps away from famous Duval Street. From here you can easily walk to all features in the historic island village.

Interior Layout:

The interior of this wooden vernacular Victorian home provides 3 stories of living space. The 1st floor is comprised of a traditional Victorian parlor style living room, 'game-room' style family room, full dining room, and a fully renovated chef’s kitchen styled with granite counter tops, tile floors, and stainless steel appliances. The 2nd floor provides 3 bedrooms and 3 bathrooms. The 3rd floor is configured as a penthouse style suite with den, and its own bathroom and kitchenette.

1st Floor: Ceilings throughout the 1st floor are an impressive 12+ feet height and the original ceiling architectural detail still exists. There are two bedrooms and two full bathrooms on the 1st floor. One bedroom provides an en-suite bathroom, and is done up in a charming New Orleans style, with a fashionable metal queen size 4-poster bed. The 2nd bedroom on the 1st floor, is set in the original mansion ‘sun room,’ a beautiful architectural space complete with Cuban tile floors, and provides a king size bed. The bathroom for the 2nd bedroom is located just steps from the bedroom.

2nd Floor: The graceful 1890’s banister staircase topped with elegant chandelier, leads to the 2nd floor to 4 more bedrooms and 4 bathrooms. All bedrooms on the 2nd floor are styled differently. The spacious front bedroom has a queen size bed and French doors that open to a porch that spans the entire width of the home with a beautiful view overlooking historic Simonton Street. The west side bedroom features a queen size pencil-style four poster bed off-set with knotty pine wainscoting, original Dade pine planked wood floors, and large sash windows to let in plenty of sun light.

The east side bedroom is in honor of Susan Watson, and features vintage wallpaper and offers wicker furnishings and a queen size bed. The back bedroom is more modern, offering a king size bed and double sets of French doors leading to a large covered terrace with a dramatic down-look view of the courtyard garden, and swimming pool below.

3rd Floor: Moving up to the 3rd floor, we find a beautiful private split-level ‘pent-house style’ suite with lounging sofa, large screen TV, small kitchen, bedroom, an additional sleeping space, and a full bathroom with tub. Since the upper level of the 3rd floor also provides all these amenities on a private floor, it is an ideal place for a couple who are traveling with a group to find a private “love nest.”

The focus of the space is the media area with lounging sofa and large screen TV on the first level. The scene is set with beautiful hardwood floors. It is built-out to feel spacious with soaring ceilings that are set right up next to the roof line. Double sets of French doors lead to a private verandah and the additional height from the 3rd floor captures even a more dramatic view from the terrace outside that overlooks the courtyard garden swimming pool below.

A split-level floor plan inside gives it added character and dimension. It offers an entertainment area with large screen TV and lounging sofa, and a few steps up to the upper level are a cozy bedroom, an additional sleeping area, the kitchen and the bathroom.

The 3rd floor bedroom is neatly tucked into an alcove. It’s cozy, but becomes an adorable little intimate hideaway space when the double set of doors is closed. It offers a trundle bed that can be made as a king size bed or 2 twin beds. Outside the door, on the opposite side of the room, a 2nd trundle bed, that can also be made up as 2 twins or a king size bed, offers a 2nd sleeping space.


An added feature of the house, is the exterior switchback staircase that starts at ground level from the back yard and leads to 2nd and 3rd floors. Both the 2nd and 3rd floor offer a verandah that expands the width of the house in the back.

One of the nicest features of the back yard is the expansive ground level sun deck and swimming pool scene that connects via French doors to the kitchen. This creates an ideal setting to move comfortably between the deck and kitchen for pool- side dining and entertaining. The back yard grounds are completely fenced for private pool-side lounging and sun bathing.

The front of the home has beautiful curb appeal with large front porches on the first and second floor that overlook the estate neighborhood of Simonton Street, expansive brick driveway courtyard, and private off street parking. An historic wrought iron fence graces the front of the property.

Bedding Summary:

• First Floor - 1 king size bed, 1 queen size bed

• Second Floor- 2 Queen size beds, and 2 King size beds

• Third Floor – 2 trundle beds (can be made to 4 twin beds or 2 king beds)

Keywords: Private Victorian Estate

More Details

Property Manager
Vacation Homes of Key West (VHKW)
Speaks: english, czech, Bulgarian
Response time:
Within a few days
Response rate:
Calendar last updated:
April 11, 2018

Guestbook comments from the manager

Lovely home, well appointed. We had a problem with one shower, we called and a very polite professional young man appeared within 20 minutes to resolve the issue. We all enjoyed our stay at this lovely home.
Aug 2016
  • 1 of 3


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 5047 sq ft
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 16
  • Min. age of primary renter: 25
  • Not suitable for children
  • Parties/events not allowed
  • We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
Location Type:
  • Downtown
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning ...
  • Broadband Access
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Towels Provided
  • Washing Machine
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • 7 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
    Bathroom 6 -
    Bathroom 7 -
  • 7 Bedrooms, Sleeps 16
  • First floor: 1 Queen bed, 1 king bed Second floor: 3 queen beds, 1 king bed Third floor: 2 trundle beds (can be made to 4 twin beds or 2 king beds)
  • Books
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • Balcony
  • Deck / Patio
  • Outdoor Grill
  • Porch / Veranda
Pool / Spa:
  • Heated Pool
  • Private Pool
Onsite Services:
  • Concierge
  • Massage
  • Private Chef
  • Staff
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • outlet shopping
  • paddle boating
  • photography
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • wind-surfing
This estate home has 2 kitchens, on one the first floor, and one on the third floor. The third floor of this home has a pent-house media center.


4/5 -
(3 traveler reviews)

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Grande Dame Key West ~ This award winning renovation of a 3 - story Estate
average rating of 4.0 based on 6 reviews

Great location and beautiful old house with tons of character. Walk almost everywhere.

  • 4 of 5

We had two families stay for spring break and everyone had there own bedroom and bath. The house was clean, but some things were a bit worn...linens, bedspreads, towels, etc. the kitchen is small but stocked ok. No ice maker in the freezer, but a store right around the corner. Back deck eating area was nice so never used small dining area inside. By far location the biggest plus for this property.

  • Submitted: Apr 8, 2018
  • Stayed: March 2018
  • Source: VRBO, from HomeAway
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Boxborough, MA

Loved it! We hope to rent it again next year!

  • 4 of 5

Ours was a group of 15 aged 4 to 80 and we loved the house! It's perfectly located 1 block off Duval Street and equidistant between Mallory Square and the Southern Most point. Plenty of room for the entire group to hang out, eat or play games. The kids enjoyed the heated pool even though it was in the 60's. Just one thing to consider, the third floor suite is a great space (kitchen and all), but it's only accesible from the outdoor stairs or a spiral staircase in a 2nd floor bedroom. It wasn't a problem for us (we're hoping to rent it again next year) but you should be aware of it before renting. Again, we loved it!

  • Submitted: Jan 29, 2018
  • Stayed: January 2018
  • Source: VRBO, from HomeAway
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Washington DC suburb

Fun for family reunion

  • 4 of 5

I brought a group of 21 family members with ages from 8 - 80. It is a nice house in a great location. We were one short block from Duvall street and walking distance to many of the attractions - southernmost point, Hemmingway house, Fort Zachary state park and the marina near the Westin. The grocery store is just around the corner so we could carry everything and we did not need cars. The house is pretty and most of it has been renovated. The dishwasher did not work but they tried to fix it and then replace it but could not do it during the holidays. The management offered to send someone to wash dishes but we declined. The area can be a little noisy. We did not hear noise from the crowds as much as the roosters. (For some historical reason, Key West has roosters wandering the town. They like to announce morning starting at about 4 am.) We rented both the 7 bedroom and 4 bedroom 'attached' house. The 4 bedroom is newer and in better shape. Overall, we had a good time and the rental was good.

  • Submitted: Jan 5, 2015
  • Stayed: December 2014
  • Source: VRBO, from HomeAway
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Car: not necessary

This estate is located in the center of the heart of Old Town Key West Historic District - just one short street of the center of Duval St.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Processing $75 + Tax
Pool Heat $150
Cleaning $475 + Tax
Tax Rate 12.5%

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

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