Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Dont miss the chance to own a piece of Key Wests past while shaping its future with this truly one-of-a-kind property.

Exclusive opportunity to own one of the largest TRANSIENTLY licensed properties in Old Town Key West. 11 Br, 11Ba, 2 pools, 2 transient licenses, and off street parking for 4+ vehicles. The Watson House is Located centrally on Key Wests most iconic street and only 1 block off Duval street. The Grand Estate is comprised of a 7 Bedroom Mansion and a 4 bedroom Villa. Each home offering a private pool.The mansion was refitted by a local designer in July 2022, including fresh paint and new furniture. Upon entering the mansion you will be greeted with 12 foot soaring ceilings, 2 first floor guest rooms with bath, parlor, living room, dining room and kitchen. The kitchen opens up to a private pool with decking and lounge chairs. A large family style outdoor table is provided for dining al fresco. Heading back inside you will take the Victorian staircase to the second floor. On the second floor you will find 4 bedrooms with en suite baths. The front primary suite offers a private balcony overlooking Simonton Street. A secondary balcony is provided for the rear primary suite overlooking the pool. Take the spiral staircase to the third floor and you will discover a large third floor private suite. Bright and airy the suite provides a living room, wet bar and balcony overlooking the pool. All three floors can also be accessed by exterior and interior staircases. Going back into the parking area, you will take a side entrance to the villa. The villa was renovated to the studs in 2014 with modern and sleek finishes. The villa offers 4 bedrooms and 4 baths, full kitchen, living room, private pool and outdoor bar. The 2 transient licenses give versatility for the property to be rented as an 11 bedroom and 11 bath estate or rented separately as a 7br main house and 4br villa. There are few large estates in Key West, which gives way to its popularity and advance bookings.

Located in picturesque Old Town of Key West, just steps from lively Duval Street, Douglas House is a captivating guest house ensemble. Spanning across five interconnected lots, with dual street access from both Amelia and Virginia Streets, this property is a remarkable collection of 15 licensed transient accommodations and a historic 5-COP liquor license + a parking lot. Douglas House, a cherished Inn, stands out for its perfect balance of accessibility and affordability, coupled with its recent renovations, ensuring it remains in pristine condition. At its heart lies a beautifully designed pool and bar area, enveloped by lush, tropical greenery, offering a tranquil oasis amidst the vibrancy of Key West. The guest house presents a variety of lodging options, from cozy queen rooms to expansive suites equipped with bars and kitchens, all featuring a modern decor. Many of these suites offer the added luxury of private porches or balconies, overlooking the garden and pool. Guests are treated to an array of amenities including a refreshing swimming pool, a charming bar area, off-street parking, and relaxing garden spaces with winding brick paths. Complimentary Wi-Fi and tea & coffee service add to the comfort of the stay. Moreover, the Douglas House is within a short stroll of Key Wests renowned attractions such as the Ernest Hemingway House, Southernmost Point Monument, and Sunset Pier at Mallory Square, not to mention the array of galleries, eateries, bars, and shops nearby. NOW INCLUDED in the offering is a valuable parking lot at corner of Amelia St at 1108 Whitehead St., for added income.

The Paradise Inn, with its subtle luxury and Bahamian charm, is situated in the center ofOld Town Key West only a short walk or bicycle ride from the shops at Mallory Square, Duval Street, The Ernest Hemingway Home, and The Key West Butterfly Conservatory. The Hotel features an upscale amenity base including spacious gardens filled with exotic flora, a fountain-fed pool, jacuzzi, complimentary breakfast, daily wine & cheese happy hour, and 24-hour coffee. Ownership also owns a two-story building next to Paradise, on 817 Simonton Street, where there is a fully renovated 2BR/1BA apartment, with private balcony, and washer and dryer on the second floor. On the first floor thereis a commercial space that is currently leased out as a SPA. There are also six parking spaces at this Property.

Located just a block from Duval Street, Cabana Inn is hidden amongst shady trees to create a tranquil paradise. The historic conch estate, with cottages that were meticulously converted into a comfortable Key West hotel, features modern designs throughout the interior and exterior.Featuring 24 rooms that can accommodate one to five people, the Cabana Inn offers ten room types. Hotel amenities include lush interior courtyards, a refreshing lagoon style pool, a spacious in-ground Jacuzzi, and a large sun-yard with treetop walkways. The 16-room employee housing neighbors Cabana Inn as well.

Located on the northside of Old Town only two blocks from the historic Key West Port,NYAH is walking distance from the main strip of bars and restaurants on Duval andproximate to historical landmarks such as the Southernmost Point, Ernest HemingwayHome, Key West Butterfly Conservatory, and Mallory Square. The Property is designed for hosting group travelers offering both private and shared guestrooms. Private Rooms can accommodate groups of up to six people and each guest is provided their own bed, locker, and set of towels. Guestroom amenities include en-suite bathrooms, private lockers, and personal charging docks. Home to three outdoorpools, NYAH is in possession of a bar license and serves drinks from the front desk. NYAH also features an office space which can be converted into a 3-bedroom transient unit. As the Property holds 36 transient licenses, no additional ROGO is needed.

Located at 521 United Street, the Southernmost Inn was originally built in the 1800s as a Francisco Marrero cigar factory. With much of the old cigar factory features restored, the award-winning transformation allowed the old Key West designs to live on throughout a modern-day establishment. The Southernmost Inn offers 38 newly renovated rooms featuring modern interiors with a classic neo-colonial design. All guestrooms feature en-suite bathrooms, flat screen TVs, and colonial wooden blinds. The Boutique also boasts a gorgeous outdoor common area with lush gardens, two pools, one jacuzzi, a bar (currently closed), and a relaxing dining area.