WINDWARD SOUTH — Your Peaceful Retreat in the Heart of Old Town Key West

Welcome to Windward South, a beautifully appointed 2-bedroom, 2.5-bathroom tropical haven perfectly positioned in the highly coveted Old Town Key West neighborhood. Just steps from Duval Street, the Ernest Hemingway Home & Museum, art galleries, iconic architecture, top-rated restaurants, lively pubs, and the island energy that makes Key West legendary, this home puts the best of the island right at your doorstep.

Bright, Welcoming & Designed for Easy Living

Step inside to a warm, thoughtfully crafted main level that invites you to unwind the moment you arrive. The spacious living room features plush seating, perfect for morning coffee, afternoon downtime, or relaxing evenings. Two sets of French doors fill the space with natural light and a breezy tropical atmosphere.

A formal dining room sits just off the living area—ideal for shared meals, puzzles, games, or simply gathering together. The fully equipped kitchen has everything you need for effortless cooking and opens to the backyard through another set of French doors, blending indoor comfort with outdoor charm.

A cozy first-floor guest suite offers ground-level convenience, perfect for anyone who prefers to skip the stairs. A stylish half bathroom completes this level, adding extra comfort for residents and guests alike.

Second-Floor Primary Suite: A Private Island Sanctuary

Ascend the spiral staircase to discover the crown jewel of Windward South: an entire second floor dedicated to the expansive primary suite.

This luxurious and serene retreat features:

✨ A plush king-size bed

✨ Soft natural light and airy island-inspired décor

✨ A spacious, private layout made for relaxation

✨ A beautifully appointed en-suite full bathroom

This exclusive floor offers unmatched privacy—an ideal setting for couples or anyone craving a peaceful, rejuvenating escape.

Outdoor Living: Your Tropical Oasis

Step out back to enjoy the best of Key West outdoor living. The private backyard features a lagoon-style swimming pool, perfect for cooling off on warm afternoons. And with seasonal pool heating, you can enjoy soothing dips all year long.

Comfortable outdoor seating invites you to lounge under the sun, sip morning coffee in the breeze, or enjoy cocktails and conversation at dusk. A gas grill makes island-style cooking easy, whether you’re grilling fresh seafood or preparing a relaxed meal with loved ones.

Everything You Need for a Carefree Stay

✔ Parking for two vehicles in the driveway and in front of the home — an Old Town luxury

✔ Efficient A/C and heating for cool comfort in every season

✔ Thoughtfully designed spaces for morning routines, post-beach relaxation, or winding down after exploring

Your Key West Escape Starts Here

Windward South isn’t just a vacation rental—it’s a place to reconnect, recharge, and create lifelong memories. With its unbeatable location, comfortable interior, serene outdoor oasis, and the luxurious privacy of the second-floor primary suite, this home delivers the very best of the Key West lifestyle.

Whether your trip is about romance, relaxation, adventure, or celebration, Windward South welcomes you with comfort, charm, and unforgettable island warmth.

Make your Key West vacation one for the books. Book your stay at Windward South today.