SIMONTON COURT HISTORIC INN & COTTAGES, Key West

Simonton Court Historic Inn & Cottages - A tropical adult-only retreat with four pools, historic cottages, and lush gardens in Old Town Key West

Simonton Court Historic Inn & Cottages features 30 unique rooms spread across five buildings on a two-acre property, including restored 1880s cigar factory cottages with exposed Dade County pine and private porches. Guests can choose from accommodations like the King Suite, Poolside, with a wet bar and private deck, or the Deluxe Cottage, offering a kitchenette and space for up to four guests. The property includes four outdoor pools, a complimentary continental breakfast with optional $5 mimosas or Bloody Marys, and Happy Hour events at the Mansion Bar. Located in Duval, the inn is a five-minute drive from the Southernmost Point and within walking distance of landmarks like the Ernest Hemingway Home and Museum. A continental breakfast is available each morning at Simonton Court Historic Inn & Cottages.

Pros

Four outdoor pools surrounded by tropical gardens and historic architecture.

Complimentary continental breakfast with optional alcoholic beverages.

Proximity to Key West attractions, including Duval Street and Mallory Square.

Unique room options, including cottages with private porches and wet bars.

Adults-only policy ensures a quiet, relaxed atmosphere.

Cons

No on-site full-service restaurant, only light breakfast and drink options.

Some rooms have shared porches or direct pool access, which may lack privacy.