Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resort. This adult-focused retreat blends historic island character with full access to one of Key West’s most iconic resort experiences. Guests enjoy "stay at one, play at all" access to the full Southernmost campus, including 3 heated pools, a private beach, oceanfront bars, tropical gardens, daily activities, and a world-class spa. Walk to the Southernmost Point, step onto South Beach, or spend the day exploring Old Town before returning to a peaceful guesthouse setting designed for laid-back island living.
✨ Why Guests Love Staying Here
▶ Booking a room at The Guesthouses means enjoying an intimate boutique experience while gaining full "stay at one, play at all" access to the expansive Southernmost Beach Resort campus:
• Quiet End of Duval Street – Stay in the heart of the action but tucked away in a peaceful, sophisticated adult-focused sanctuary.
• Private Beach Access – Relax on the resort's exclusive tanning pier and private beach area with complimentary loungers.
• 3 Heated Pools – Choose your vibe between the lively Shores Pool, the tranquil Pineapple Pool, or the South Beach Pool.
• Tropical Gardens & Hammocks – Meander through award-winning lush grounds filled with hidden seating nooks and swaying hammocks.
• Daily Resort Activities – Enjoy poolside yoga, live music, and lawn games like cornhole and giant Jenga.
• Full-Service Concierge – Expert local advice for booking sunset sails, bike rentals, and the best island dining.