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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Classic Key West Estate ~ Spectacular Historic Seaport Home

Bedrooms 7
Space 4,000 sq. ft.
Property type house
Minimum Stay 3 - 5 nights


About the property

Estate Home + Private Pool-Side cottage, 7 Bedrooms-5 Bathrooms, Sleeps 10-14

Featured on the HGTV House Hunter's on Vacation series in July 2011, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once dream-worthy, 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 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.

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.

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, cook's island, and beautiful wooden dining table, this luxurious kitchen has French doors that lead to the pool and deck area. The layout is ideal for entertaining. The wooden table has the added feature of expanding to seat your group for sit-down meals.

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 conveniently positioned near the kitchen doorway. There is plenty of seating for sunning and lounging.

Pool Side Cottage: 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 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 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 full (double) Murphy bed, 2 queen sleeper sofas.

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.

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.

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.

Keywords: Estate Home

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:
January 29, 2018

Guestbook comments from the manager

The house was perfect! The week before we arrived they had repainted the entire interior of the house. It was beautiful! All new linens and towels, new appliances, new washer/dryer, etc. Our family was there for a wedding - there were 12 of us staying there and there was plenty of room for everyone. The mattresses were very comfortable. The pool was so much fun to cool off in after a long day of sightseeing. I noticed a comment saying that there weren’t chairs, etc. for everyone to sit by the pool, but there were plenty, We used the grill a few nights - worked great! The location of the house is within walking distance of Duval Street as well as many restaurants. We feel so fortunate to have found such a great house to spend the week together with family.
Sep 2015
  • 1 of 2


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 4000 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 14
  • Min. age of primary renter: 25
  • Children welcome ...
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
Location Type:
  • Downtown
  • Near The Ocean
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Broadband Access
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Telephone
  • Towels Provided
  • Washing Machine
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • 5 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
  • All bathrooms are nicely styled and up to date while keeping design integrity of the home.
  • 7 Bedrooms, Sleeps 14
  • Bedroom 1 - 1 king , French doors open to pool deck
    Library - 1 double , Murphy bed drops from wall to make comfortable bed
    Private pool-side cottage bedroom - 2 double , 2 doubles can be pushed together. Private bath.
    Bedroom 4 - 'Anne's room' - 1 king
    Bedroom 5 - 'Jack's room' - 1 king
    Bedroom 6 - 'Executive Suite' - 1 king
    Bedroom 7 - 1 king
  • All bedrooms are beautifully appointed. 1st floor has 1 king size bed, 1 full (double size). 2nd floor has 4 king size beds. Pool-side cottage has 2 full-size double beds.
  • Books
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Television
  • Balcony
  • Deck / Patio
  • Golf ...
  • Kayak / Canoe
  • Lawn / Garden
  • Outdoor Grill
  • Tennis ...
Pool / Spa:
  • Heated Pool
  • Private Pool
Onsite Services:
  • Concierge
  • Massage
  • Private Chef
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • eco tourism
  • outlet shopping
  • paddle boating
  • photography
  • shopping
  • shuffleboard
  • 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
  • fly fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • wind-surfing
This unique estate property is in a prime Downtown location in the Historic Seaport neighborhood. Neighborhood has beautiful curb appeal. Mixed residential and commercial. Walk to all Old Town features. 5 minute walk to Duval Street.


3/5 -
(3 traveler reviews)

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Classic Key West Estate ~ Spectacular Historic Seaport Home
average rating of 3.0 based on 5 reviews

Excellent stay

  • 4 of 5

My friends and I rented this house for a vacation. The house and management team were excellent and the accommodations were superb! This rental was in close proximity to good restaurants and nightlife as well...Overall we had a great trip and stay, and would most definitely return!

  • Submitted: Feb 8, 2017
  • Stayed: September 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
6 1
Loganville GA

Are you kidding me???

  • 1 of 5

Well at first glance this "HGTV" home is lovely....however after being gone for the day at lunch and sightseeing, getting back to the home full of termites is anything but spectacular. Termites in our beds, crawling in our clothes we had put away, crawling in our children's diapers and toys, all over pillows and lamps. When attempting to contact the rental company, there is not a specific 24 hour number. Instead, you call the number and are given instructions for after hours emergencies. Apparently, this company does not value customer service as we called several times FOUR HOURS ago and left several messages. This is unacceptable and really unbelievable that someone would see this property as fit to rent. There is NO WAY that this problem just started today. The patchwork and rotted placed in the floor are throught the house. The amount of time spent to plan this trip for 10 adults and 3 children is so disappointing. My aunt put this trip together as a final farewell to her husband she lost last year. The two of them traveled to Key West for over twenty years and loved it so much and had so many wonderful memories that she wanted to share with us.

  • Submitted: Jun 7, 2014
  • Stayed: June 2014
  • Source: VRBO, from HomeAway
Owner's Response: We are really sorry this guest's stay was interrupted by termites swarms. Termites are everywhere in Key West and unfortunately it can not be predicted when they will come out swarming. Even though it is unpleasant to have flying bugs around - they are absolutely harmless. The guest called late at night on Saturday and their call was returned on Sunday morning. They were relocated the same day as termites normally swarm for a couple of days. The house was treated for termites afterwards. In 2015 the home received a major make over - floors were refinished, decks repaired and painted, interior painted, all mattresses and bedding replaced, new furniture and more. We hope our future guests enjoy this classic home!
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22 0

Awesome location

  • 4 of 5

Awesome location great patio and pool area, we will be back!!

  • Submitted: Apr 16, 2013
  • Stayed: April 2013
  • Source: VRBO, from HomeAway
Did you find this review helpful?
5 1


Nearest Airport
0.5 Miles
Key West Int'l Airport
Nearest Barpub
Several on Duval Street
Nearest Ferry
0.1 Miles
Historic Seaport
Nearest Golf
4 Miles
Key West Golf Club
Nearest Motorway
4 Miles
U.S. Highway 1
Nearest Restaurant
Help Yourself - across the street
Nearest Beach
0.5 Miles
Fort Zachary Taylor State Park Beach
Car: not necessary

Located on Fleming St. in the famous Historic Seaport neighborhood. Prime Old Town Key West location close to the waterfront on the gulf side of the island and the original lower Duval Street area, encompasses this district. This home was built by one of the original the 'founding fathers' of the late 1800's who built the first shipping docks and warehouses, restaurants and grand homes. This home stands today as part of one of the largest and most impressive collection of turn-of-the-century architecture. This neighborhood includes famous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters, a large variety of historic homes, and Mallory Square.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $475

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

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