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Classic Key West Estate ~ Spectacular Historic Seaport Home

Old Town, Key West, FL, USA
  • House4000 sqft
  • Bedrooms7
  • Sleeps14
  • Bathrooms5
  • Half Baths0
  • Mininum Stay3 - 5 nights

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

Property Manager

Vacation Homes of Key West (VHKW)

Member Since 1997
Response rate:
Response time:
within one day
english, czech, Bulgarian
Calendar last updated:
Apr 03, 2018


    • Internet
    • Air Conditioning
    • Swimming pool
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • TV
    • No Smoking


      • 7 Bedrooms, Sleeps 14
      • Bedroom 1
        1 king, French doors open to pool deck
      • Bedroom 7
        1 king
      • 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
      • 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.


      • 5 Bathrooms
        • All bathrooms are nicely styled and up to date while keeping design integrity of the home.

        Location Type

          • Downtown
          • Near The Ocean


              • Away From It All
              • Family
              • Historic
              • Romantic
              • Sports & Activities
              • Tourist Attractions


                  • Guests provide their own meals


                      • Iron & Board
                      • Air Conditioning
                      • Clothes Dryer
                      • Hair Dryer
                      • Internet
                      • Broadband Access
                      • Linens Provided
                      • Living Room
                      • Telephone
                      • Towels Provided
                      • Washing Machine


                          • Kitchen
                            Full gourmet kitchen in main home. Kitchenette in pool-side cottage
                          • Catering Available
                          • Cooking Utensils
                          • Dishes & Utensils
                          • Dishwasher
                          • Ice Maker
                          • Coffee Maker
                          • Microwave
                          • Oven
                          • Refrigerator
                          • Stove
                          • Toaster


                              • Dining
                                Dining table in kitchen.
                              • Dining Area


                                  • Books
                                  • CD Player
                                  • DVD Player
                                  • Satellite / Cable
                                  • Television


                                      • Balcony
                                      • Deck / Patio
                                      • Golf
                                        Key West Golf and Country Club is open to the public
                                      • Kayak / Canoe
                                      • Lawn / Garden
                                      • Outdoor Grill
                                      • Tennis
                                        There are 2 nice public courts

                                        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

                                                      • photography
                                                      • antiquing
                                                      • boating
                                                      • eco tourism
                                                      • outlet shopping
                                                      • paddle boating
                                                      • bird watching
                                                      • 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

                                                              • parasailing
                                                              • basketball court
                                                              • deepsea fishing
                                                              • fishing
                                                              • fly fishing
                                                              • golf
                                                              • jet skiing
                                                              • kayaking
                                                              • cycling
                                                              • 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.

                                                                    House Rules

                                                                    Check-in: 4:00 PM

                                                                    Check-out: 10:00 AM

                                                                    Cancellation Policy

                                                                    Canceled bookings will not receive a refund

                                                                    3 Reviews


                                                                    Latest reviews

                                                                    Excellent stay

                                                                    Cassie C.

                                                                    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!

                                                                    Are you kidding me???

                                                                    jenni H.Loganville GA

                                                                    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.

                                                                    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!

                                                                    Awesome location


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


                                                                    Old Town, Key West, FL, USA

                                                                    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

                                                                    Additional information about rental rates

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                                                                    Tax Rate
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                                                                    For booking assistance, call 888-640-7927

                                                                    Property # 138048