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

Discover the perfect blend of comfort, charm, and tropical elegance at Windward South, a beautifully appointed 2-bedroom, 2.5-bathroom home ideally situated in the highly sought-after Old Town Key West neighborhood. This inviting getaway places you just steps from iconic sites such as world-famous Duval Street, the Ernest Hemingway Home and Museum, art galleries, historic architecture, top-rated restaurants, lively pubs, and the vibrant energy that defines Key West.

A Warm and Inviting First Floor
Step inside to a bright and thoughtfully designed main level that immediately welcomes you with warmth and style. The spacious living room provides plush, comfortable seating—perfect for enjoying mornings with coffee, unwinding after island adventures, or spending time together in the evenings. Two sets of French doors fill the space with natural light, creating a relaxing tropical ambiance.

Adjacent to the living room is a formal dining room, ideal for shared meals, puzzles, games, or relaxing gatherings. The fully equipped kitchen offers everything you need for effortless vacation cooking and also opens to the backyard through another set of beautiful French doors.
A cozy guest suite is located on this level, offering convenience and comfort for guests who prefer to avoid stairs. A stylish powder room adds convenience for everyone staying at or visiting the home.
Primary Suite: A Luxurious Second-Floor Sanctuary

Ascend the spiral staircase to discover a truly exceptional feature of Windward South: the entire second floor is dedicated to the expansive primary suite.
This serene retreat offers complete privacy and comfort, making it an ideal sanctuary for rest and rejuvenation. The suite features a luxurious king-size bed, generous natural light, and sophisticated island-inspired décor. The spacious layout provides room to relax, refresh, and recharge in total comfort. A beautifully appointed en-suite full bathroom completes the space, offering both convenience and a sense of indulgence. This private level of the home makes the primary suite the perfect haven for couples or anyone seeking quiet relaxation during their stay.

Outdoor Living at Its Finest
Step outside to your own private tropical oasis. The backyard features a lagoon-style swimming pool, ideal for cooling off during warm Key West afternoons. Seasonal pool heating ensures that you can enjoy soothing swims year-round.
Comfortable outdoor seating invites you to lounge under the sun, enjoy morning coffee in the breeze, or gather for evening cocktails and conversation. A gas grill makes outdoor cooking easy and enjoyable, whether you're preparing fresh seafood or grilling a casual meal with family and friends.

Comfort, Convenience & Everything You Need! Parking is simple and stress-free with space for two vehicles in the driveway and in front of the home—an invaluable perk in the heart of Old Town.
The home stays cool and refreshing thanks to efficient air conditioning and heating, ensuring comfort in every season. Whether you're getting ready for the day or winding down after exploring the island, every space feels soothing, cozy, and thoughtfully designed.

Your Key West Escape Starts Here
Windward South is more than a vacation rental—it’s a place to unwind, reconnect, and create unforgettable memories. With its ideal location, comfortable living spaces, serene outdoor oasis, and beautifully designed suites—including the private second-floor primary retreat—this home offers everything you need for a brilliant getaway.

Whether you're visiting for romance, relaxation, adventure, or celebration, Windward South is ready to welcome you with the comfort and charm that make Key West unforgettable.

Make your vacation one for the books with a stay at Windward South.