SIMONTON COURT HISTORIC INN & COTTAGES, Key West – Your ideal downtown stay

Simonton Court Historic Inn & Cottages - Adult-only historic inn near Southernmost Point

Simonton Court Historic Inn & Cottages is an adult-only property located in Old Town Key West, a 5-minute drive from the Southernmost Point of the continental United States. The property features four outdoor pools, lush gardens with restored Victorian and Conch architecture, and historic cottages originally built in 1880 for cigar factory workers. Guests have access to a complimentary continental breakfast, free Wi-Fi, and a 24-hour front desk. The property includes a tropical pathway known as Hurricane Alley, leading to cottages with exposed Dade County pine and private porches. Nearby attractions include Duval Street, Mallory Square, and the Key West Shipwreck Treasure Museum.

Additional perks of the hotel

Complimentary drink ticket per guest (Breakfast Cocktail or Happy Hour Cocktail)

Breakfast to-go option available

One complimentary active day pass (gym or bicycle rental)

Happy Hour with $5 drinks and snacks (Friday to Sunday, 3-5 PM)

Welcome Hour with $5 cocktails (Monday & Thursday, 3-4 PM)

On-site bike rentals ($20/day, one day complimentary with direct booking)

Key West Fitness Center access ($15/day, one complimentary pass with direct booking)

Yoga & meditation space by the Mansion pool

Rooms & Cottages

The property offers 30 unique rooms across five buildings, including historic cottages, a Victorian mansion, and an 1880s cigar factory. Cottages feature exposed Dade County pine, wood floors, and private porches, accommodating up to four guests with king or queen beds and loft sleeping areas. The Mansion includes a Bahamian-style residence with a poolside breakfast bar. The Historic Inn retains original cigar factory details with tropical Florida décor and a black-bottom pool. Manor House is a restored Conch-style shotgun house. Room types include Petite Queen, Deluxe Queen, Standard King, Deluxe King, King Suite (Poolside), Standard Cottage, and Deluxe Cottage.

Other conveniences

Air conditioning and ceiling fans

Mini-bar and tea/coffee maker

Safe deposit box and TV

Ironing facilities and garden furniture

Wet bar in select cottages and suites

Private porches, sundecks, or balconies

Poolside service and honor bar

Room service for beverages and snacks

Complimentary Keurig coffee in rooms

Complimentary local brew, iced/hot tea, and filtered water at the pool bar