Simonton Court Historic Inn & Cottages

Nestled in the heart of Old Town Key West, Simonton Court Historic Inn & Cottages offers a lush, adults-only tropical retreat that blends Victorian charm with laid-back island elegance. Once a historic cigar factory, this tranquil inn now spans two beautifully curated acres, featuring four serene swimming pools, fragrant gardens, and lovingly restored architecture including conch cottages, a grand mansion, and cozy townhouses.

Guests can unwind in accommodations ranging from Deluxe King Rooms in the Mansion to quaint historic cottages with southern-style porches and exposed Dade County pine. Each space is thoughtfully designed to reflect Key West’s storied past and artistic spirit, with original works from local artists available for purchase.

Amenities include complimentary continental breakfast, poolside drink service, daily housekeeping, and on-site bike rentals. Unwind with $5 cocktails during Welcome Hour, enjoy a Sunday Aqua Yoga class, or explore the surrounding neighborhood during the weekly Simonton Court Food Tour.

Whether soaking in the sun, relaxing under palm trees, or enjoying a curated Romance or Birthday Package, guests find this boutique inn to be an ideal escape for couples and solo travelers alike. Located just off the beaten path, Simonton Court offers quiet luxury just steps from Key West’s historic attractions and vibrant energy.

With exceptional service, timeless style, and thoughtful extras like room service, mini bar offerings, and concierge recommendations, Simonton Court Historic Inn & Cottages provides an unforgettable romantic getaway in one of the island’s most iconic settings.