This gorgeous two-cottage property is located at the top of Solares Hill in the heart of Old Town Key West and offers exceptional flexibility along with strong rental and income potential. The lovely main house sits at the front of the property and features a main-floor primary bedroom and bath, an open living and dining area with vaulted ceilings, and central air. Stairs lead to a second bedroom at the rear of the home, while an open loft at the front provides ample storage. The kitchen showcases white and gray quartz countertops with stainless steel appliances. Both the kitchen and the main-floor bedroom open to a back deck overlooking the pool and tranquil water features, creating a private oasis ideal for seating, dining, and lounging. A pathway along the pool leads to the charming guest cottage, which offers its own private patio and French doors opening to a first-floor living space with dining area and breakfast bar. A spiral staircase leads to the oversized second-floor bedroom with ensuite bath, filled with beautiful soft natural light. The cottage is ideal as a guest house, long-term rental, or income-producing vacation rental, while the main home can also generate rental income or be owner-occupied for flexible living arrangements. The main house received new impact windows and upgraded plumbing and electrical and a new structural beam in 2019, new siding in 2022, and a full exterior repaint in 2025. The cottage was taken down to the studs and fully renovated in 2020. The pool with water feature was added in 2020 along with new walkways and thoughtfully designed landscaping. Both homes have new roofs installed in 2019, on-demand water heaters, separate washers and dryers, and are being sold turn-key, artwork excluded—making this a move-in ready property with immediate income potential in one of Key West's most desirable locations.