Southernmost Point Guest House and Garden Bar - Historic Key West B&B

Southernmost Point Guest House – Historic Key West Guest House Near Duval Street

Southernmost Point Guest House stands as a landmark 1894 Victorian mansion and one of Key West’s most celebrated historic stays. Originally constructed for cigar magnate Eduardo H. Gato, the residence became an island legend when the entire home was famously moved by mule teams to achieve the ideal sunset-facing orientation—resulting in the only odd-numbered address on the even side of Duval Street: 1327 Duval St. Today, this historic Key West guest house blends classic architectural charm with warm island hospitality, offering a genuine Old Town experience anchored in heritage.

For more than three decades, the Santiago family has operated the guest house, now into its third generation. The property continues to evolve under Sandy Santiago Jr. and Talia Santiago-Jones, a sixth-generation Conch. Recent additions include the Southernmost Point Bar (2020) and Southernmost Sandy’s Café food truck (2022), enhancing the guest experience with casual island flavors and tropical cocktails just steps from the rooms.

Located on the serene southern end of Duval Street, guests enjoy immediate access to the Southernmost Point Buoy (110 meters) and South Beach (73 meters), placing ocean views, shoreline relaxation, and iconic photo spots right outside the gate. The Key West Butterfly & Nature Conservatory is next door, while the Ernest Hemingway Home and Museum sits a pleasant 10-minute walk away—close to the action yet far enough for quiet evenings under swaying palms.

The inn features 13 unique guest rooms across four historic buildings, each designed with individual character and furnished with:

• Air conditioning and heating

• Flat-screen TVs and high-speed Wi-Fi

• In-room refrigerators and coffee makers

• Plush bedding in queen or king configurations

• Private bathrooms with daily housekeeping

• Select balconies, porches, or terraces overlooking tropical gardens

Guests receive an impressive collection of complimentary perks with zero resort fees, including:

• Hot American breakfast daily

• Evening happy hour featuring a complimentary drink at the Garden Bar

• Free off-street parking

• Spa pool & sundeck surrounded by lush landscaping

• Beach towels and on-site bike rentals

• Around-the-clock guest support

Steps from historic mansions, outdoor dining, boutiques, art galleries, and charter experiences, Southernmost Point Guest House offers a front-row seat to Key West culture. After exploring Duval Street’s live music and waterfront adventures, guests return to a peaceful garden retreat where they can unwind with a cocktail and enjoy the evening breeze—capturing the timeless spirit of the island.

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