Step back in time and experience the Old Florida Lifestyle in the heart of Longboat Keys historic Longbeach Village! Tucked away on the northernmost end of the island, this rare property features two charming Key Weststyle beach cottages on one lot, surrounded by lush tropical landscaping for a truly private island retreat. The main updated cottage offers a light filled, open floor plan with 2 bedrooms, 2 bathrooms, a den, laundry room, and spacious living area. The kitchen was tastefully updated in 2021 with quartz countertops, hardwood cabinets, and newer appliances, complete with a breakfast bar for casual dining. Open the windows and let the coastal breeze fill your home, or step outside to the wooden deck and tiki barperfect for entertaining and enjoying evenings listening to the nearby Gulf waves. Across the wooden overpass sits the guest cottage, a cozy retreat with 1 bedroom, 1 bathroom, full kitchen, living space, and a private porch. It even has its own access via the private alleyway, making it ideal for visitors or rental potential. Additional updates include Hardie board siding (2021), appliances (2021), quartz countertops (2021), cabinets (2021), and A/C (2017), ensuring modern comfort while maintaining that laid back island vibe. With no HOA or deed restrictions, this property offers flexibility for personal use or investment. Best of all, its just steps from both the beach and the bayenjoy Whitney Beach, two fishing docks, the community boat/kayak launch, and popular dining at Mar Vista and Shore.