Simonton Court Historic Inn - Adult-Only Old Town Retreat

Simonton Court Historic Inn & Cottages – Adult-Only Historic Retreat in Old Town Key West

Simonton Court Historic Inn & Cottages stands as one of Key West’s premier adult-only historic escapes, offering an elevated blend of 19th-century Victorian craftsmanship, restored Conch architecture, and modern boutique luxury. Spanning two acres of secluded tropical grounds in the heart of Old Town, this award-winning Moloney Smith property delivers an exclusive child-free sanctuary designed for travelers seeking sophistication, tranquility, and authentic Key West heritage just one block from Duval Street.

A curated collection of 23 distinctive accommodations showcases the artistic direction of Susan Moloney, featuring century-old architectural details, hand-selected furnishings, and refined contemporary amenities. Deluxe Queen Rooms in the Main House and Pool House highlight original heart-pine floors, 12-foot ceilings, and private verandas framed by lush foliage. Standard King Rooms inside the 1880s Eyebrow House offer private entrances opening onto hidden garden paths, complemented by handcrafted four-poster beds, marble wet bars, and premium bath amenities. The Poolside King Suites feature private French-door access to the Main Pool’s courtyard, separate living areas with sofa sleepers, and spa-like bathrooms—the ideal layout for couples seeking extra space. For the highest level of privacy, the Historic Cottages—including the Gatehouse and Carriage House—provide full Viking-equipped kitchens, wraparound porches, secluded garden views, and preserved 1800s design elements blended with modern luxuries.

Guests enjoy access to four distinct swimming pools—a rare amenity in Key West. The Main Pool features zero-entry access under towering Royal Poincianas; the Garden Pool offers a quiet, narrow lap-style layout within the most private section of the grounds; the Courtyard Plunge Pool creates an intimate escape near the cottages; and the Upper Pool delivers elevated sunshine and panoramic garden scenery. More than 50 species of tropical plants shape the immersive landscape, with brick pathways leading to water features, meditation nooks, and shaded alcoves designed for quiet relaxation.

Located in a prime Old Town position while maintaining a whisper-quiet atmosphere, Simonton Court provides effortless access to Hemingway Home, Key West Lighthouse, Mallory Square, the Historic Seaport, and Simonton Street Beach. The property’s “living design” philosophy showcases curated international art, Cuban-influenced tilework, and preserved Key West artifacts, creating a boutique environment steeped in cultural significance. Simonton Court Historic Inn & Cottages represents a rare blend of preserved Key West history and contemporary adult-only luxury—an oasis ideal for romantic escapes, milestone celebrations, and travelers seeking serene, culturally rich accommodations in the heart of Old Town.

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