The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. These two beautifully renovated historic structures provide 10 bedrooms and 7.5 bathrooms. This is a remarkable place for family and friends to stay together in a Key West weekly rental. Spacious and luxurious, this estate is gated and fenced with a pool, decks, and tropical gardens. To top it off, the property is located in the sought after 19^th century Historic Seaport neighborhood.

The picturesque Key West Seaport is just 3 short streets away. Strolling to the harbor takes you past grand wooden homes and adorable cottages hand-built by seafaring merchants. Narrow island streets and lanes line the neighborhood punctuated with white picket fences.

A Bit of History

The Key West Historic Seaport neighborhood was the first area to be developed on Key West. Most don’t realize that the bravest of these early builders were 1700's British loyalist settlers of the Bahamas. These forefathers and mothers created an established sailing route between the sleepy Green Turtle Key in the Bahama Bahamas and the growing trade center of Key West.

Over the ensuing 150 years, many British settlers gradually relocated to Key West. Rather than leave home behind, some literally disassembled their wooden houses, and floated them over to Key West and rebuilt them. This remarkable time established architectural roots that still bind the two island cultures together.

During the early 19^th century building frenzy, the seaport became a major world trade center. Regrettably old growth heart pinewood forests in the Florida Keys were decimated by rakish settlers. In return for being cut down, trees were milled into boards that still remain nearly imperviable.

The loss of the old pine forests was partially reconciled with the wooden structures built near the Key West Historic Seaport. Skilled carpenters milled the trees and fashioned the gold colored boards into craftsman structures - from warehouses, to sail lofts, to merchant shops, to hotels, to domiciles. What remain standing in the wake, is a cherished collection of one-of-a kind wooden buildings. Fortunately, unlike the old growth trees, the historic Old Town Key West houses are now permanently protected. They will sustain the changing times. 

More than a century has past since most of the buildings were constructed. While many of the structures still stand, their private and commercial use has changed with the times. Sail lofts, warehouses, canneries, and stables have been transformed into a new wave of fashionable enterprises. While the outside of the structures held their original form, inside they’ve been transformed into remarkable places.

Local Destinations

From the Old Town Caribbean Estate, you’ll enjoy easy walking access to some of the best locally owned and operated destinations. From breakfast to late night music, so many options are just a few minutes away. Begin your day with a famous breakfast place. One of the oldest on the island is Pepe’s Café. Other local favorites include the Fisherman’s Café, and Harpoon Harry’s. Enjoy your break from shopping malls and discover island clothes at Local Color. Find some extraordinary housewares at Island Love Story. Then thanks to the efforts of the Schooner Wharf Bar, you can enjoy cherished wooden schooner sailing ships and enjoy live music at one of the oldest bars on the island. Looing for some handcrafted beer? Pop into The Waterfront Brewery, and when you’re ready for casual yet elegant dining, we recommend the Mediterranean restaurant Azur.

No matter what time of day or evening, there is something special to see and do in the Historic Seaport neighborhood. No doubt as you wander, shop, dine and imbibe, you’ll be looking forward to the comfort and luxury that awaits you at the luxurious 10BR 7.5 BA Old Town Caribbean Estate.   

LAYOUT

The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. These two beautifully renovated historic structures provide 10 bedrooms and 7.5 bathrooms. This is a remarkable place for family and friends to stay together in a Key West weekly rental. Spacious and luxurious, this estate is gated and fenced with a pool, decks, and tropical gardens. To top it off, the property is located in the sought after 19^th century Historic Seaport neighborhood.

The layout of the property provides two separate and completely different historic dwellings: The main 2-story Victorian house (Classic Key West Estate), and the luxurious Caribbean style guest house. Completely gated and fenced with a pool, decks, and gardens, this property offers an enviable setting for a gathering of family and friends in a weekly Key West vacation rental.

Main House:

Located at the front of the property, the 7BR 5.5BA Classic Key West Estate is the perfect place for your group to gather. For a full description of this 2-story Victorian home, please follow this link. The common rooms on the 1^st floor provide a spacious living room / media / dining room that connects with a renovated blue and white kitchen with stainless steel appliances and earth-tone granite countertops.

The kitchen is located at the back of the house. Two sets of French doors, at the back corner of the kitchen, lead to the pool deck and garden. Easy access to the kitchen makes the setting ideal for entertaining. The pool deck provides an elegant backyard lounging and dining area. A flat screen TV is placed on the exterior wall above the table for outside media entertainment.

All bedrooms in the main Victorian house are spacious with 12 ft ceilings, and each provides a king size bed. There are 2 bedrooms and 1.5 bathrooms on the first floor and 4 bedrooms and 3 bathrooms on the 2^nd floor.

Across the pool deck there’s a free-standing poolside cottage bedroom that provides 2 full size beds and 1 full bathroom. The privacy fence at the back of the pool deck has a gate that leads to the Private Caribbean Guest House. Open the gate for a seamless access between the two dwellings.

Caribbean Guest House:

The 3BR 2BA Caribbean Guest House is exotic, private, and luxurious!  Situated at the back of the estate property, it was completely renovated in 2021. The renovation expanded this estate to provide 10 bedrooms and 7.5 bathrooms total.

This private guest house provides a special space for the persons who desire privacy from the rest of the larger group. The property owner designed it as a luxurious peaceful retreat, with spaces to relax, read, and quietly enjoy hydrotherapy in an exotic setting.

Entering from the pool deck, the front entrance of the guest house steps into the open concept great room. Dark mahogany floors and white walls throughout the integrate the spaces throughout the house. Ceilings in many of the rooms are lined with bamboo paper, creating an exotic-tropical feel.

In the living room, bright green banana leaf print wallpaper is featured on one wall. A modern furniture grouping provides a sofa, two easy chairs, and large flat screen TV mounted on wall. For a surprise, look up! Overhead you’ll notice the unusual hammock netting stretched across part of the ceiling. Look closer for a peek-a-boo view of an unsurpassed meditation loft above.

The modern kitchen also makes an impressive statement. Bright white cabinets with an L-shape breakfast counter and top-of-the line stainless steel appliances complete the space. The kitchen ceiling is finished up to the gable roof line and lined with bamboo paper and contrasting mahogany ceiling beams.

Leaving the great room, an L-shape  hallway leads to the three bedrooms and two bathrooms. All bathrooms are elegant. The first bathroom is close to the main entrance door. Decorated in bright white with black fixtures, it offers a deep oval-shaped bathtub and a single vanity sink with three drawers. An oval mirror above the sink reflects the nature light that streams in from the three windows above the bathtub.

All bedrooms painted bright white and minimally furnished using tropical textures of bamboo, seagrass, and wicker. Each bedroom offers different bed sizes and unique features and tropical designs.

Bedroom One: Immediately to the left, the first bedroom is furnished with a full-size (double) bed with sea grass headboard. A custom spiral bright yellow metal ladder leads to the meditation loft above.

The meditation loft is set with seat pillows and lit with artistic lighting. A Buddha statue is placed on one end of the meditation room, backlit by a gable window at the front of the house. Guests are asked to use this unique space respectfully and agree to follow the posted rules, according to the rental contract.

Directly across the hallway from bedroom one, a modern design bathroom is finished in white-on-white tile and marble. The single vanity is topped with a  molded sink. The shower is oversized with a rain shower and a wand – all bathroom fixtures are an elegant gold tone.

Bedroom Two: Directly across the hall from bedroom one, the second bedroom is furnished with modern walnut tone furnishings. A platform queen size bed, featuring an abstract headboard, sits as a center piece in the bright white room. Matching end tables on either side of the bed, and a bureau complete the set. Plantation shutters on the four tall sash windows add to the minimalist island style. An exterior door to the left of the bed, leads to the bathing porch.

Bedroom Three: The third bedroom is at the end of the hallway. Larger than the other two bedrooms and providing a king size bed, it is considered the master bedroom. Golden bamboo furnishings blend beautifully with the bamboo and mahogany ceiling. French doors to the left of the bed, lead to the bathing porch.

Exotic Bathing Porch: The Caribbean-style outdoor covered bathing porch is a fabulous feature of the house. Here you enjoy an exotic bathing setting for two - with two deep clawfoot bathtubs surrounded by louvered plantation shutters. If you prefer to shower instead, there is an open shower at the end of the bathing room. The bamboo ceiling is carried to the bathing room, and louvered walls provide plenty of privacy. Hanging orchids and potted palm trees punctuate the tropical design.

Grounds: The estate grounds are fenced and gated, with curb views of each house.  The back yard the connects the dwellings is completely decked. There is a swimming pool off the back deck closest to the main house. Covered front porches on the 1^st and 2^nd floor of the main house provide views of famous Fleming St. The 2^nd floor verandah on the back of house provides a view of the pool garden below and creates a covered loggia off the pool deck. Mature palm trees and foliage create a romantic tropical setting.

Bedding Summary

 Main House:

• First Floor - Bedroom One - 1 Queen Murphy bed; Bedroom Two - 1 King size bed
• Second Floor - Bedroom Three - 1 King size bed; Bedroom Four - 1 King size bed; Bedroom Five - 1 King size bed; Bedroom 6 - 1 King size bed
• Pool-side Cottage - 2 full size (double) beds.

Guest House:

• Bedroom One – Full (Double) Bed
• Bedroom Two – Queen Size Bed
• Master Bedroom – King Size Bed

Amenities: Swimming pool, large deck, tropical gardens, expansive porches, and privacy fences. Fully equipped kitchen, central a/c, telephone, TV, stereo, washer / dryer. Linens and towels are provided.  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 Key West 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  property is situated on famous Fleming Street in the Historic Seaport Neighborhood. This tiny district 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 wooden structures are 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.