A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House—one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa—each with its own private pool. Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use. The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area. Upstairs, four en suite bedrooms include two primary suites with private balconies—one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat. The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar—perfect for entertaining. Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market—highly sought-after and consistently booked well in advance.