
Tucked behind a classic white picket fence in the heart of historic Old Town Key West, Old Town Cottage offers the perfect blend of island charm, modern comfort and an unbeatable location.
Just steps from Duval Street, you'll be within easy walking distance of Key West's restaurants, galleries, boutiques, nightlife and iconic attractions, while your private outdoor spaces give you a quiet place to relax when you're ready to slow down.

-Heidi, June 2026

Old Town Cottage offers a peaceful retreat on a quiet lane just steps from Duval Street, surrounded by historic homes, tropical gardens, restaurants, galleries, boutiques and iconic Key West landmarks. Enjoy exploring the island on foot before returning to your private outdoor space for a relaxing evening beneath the palms.
Duval Street
2 minute walk
Local Dining & Shopping
2-15 minute walk
Hemingway Home
5 minute walk
Fort Zachary Taylor Beach
10 minute walk
Live Music & Nightlife
2 minute walk


We are a locally based Key West team with an intimate knowledge of the island, from its most celebrated landmarks to its hidden gems. Our dedicated local staff is available throughout your stay to provide thoughtful recommendations, personalized assistance and discreet, attentive service.

Your cottage is cleaned, cared for and thoughtfully prepared with the details of a comfortable stay in mind, so settling in feels easy from the moment you arrive.

Settle into your own kitchen, living room, bedrooms and outdoor spaces. Stay for a month or longer and experience Key West at your own pace, with the comfort and privacy of a home rather than a hotel room.
Everything you need for an easy Key West stay.
Dogs are welcome with advance approval.
A $200 pet fee applies. There is no weight limit, although dogs must be crated when left alone and guests are responsible for cleaning up after their pets. Please contact us before booking if you plan to bring your dog.
There is a distinctive elegance to staying in the heart of Old Town Key West.
Rather than waking in a conventional resort, begin each day in the privacy of your own beautifully appointed cottage. Prepare coffee in the fully equipped kitchen, step into the warm tropical air and enjoy the rare convenience of exploring Key West's historic streets, galleries, restaurants and waterfront on foot.
Old Town Cottage offers an exceptional setting for experiencing the island at its most authentic. Duval Street is moments away, while the cottage itself is discreetly tucked along a quiet lane, creating an ideal balance of accessibility, privacy and tranquility.
Thoughtful details throughout the property capture the character of Key West while providing the comfort and ease of a private residence.
Following a day at the beach or pool, retreat to the private outdoor shower, conveniently accessed through the half bathroom and set within your secluded outdoor space. Dine al fresco, unwind on the patio with a glass of wine or allow the gentle tropical atmosphere to define the evening.
Spend your days discovering Key West's historic architecture, distinguished galleries, acclaimed restaurants and waterfront landmarks. Visit the Ernest Hemingway Home, ascend the Key West Lighthouse, explore the Historic Seaport or enjoy an afternoon at Fort Zachary Taylor State Park.
At day's end, everything you desire is close at hand. Return home on foot, pour a favorite drink, step into the evening air, enjoy a refreshing swim in the pool and rinse away the day beneath the palms before settling into the unhurried rhythm that makes Key West so enduringly captivating.
If you're looking for a Key West vacation rental near Duval Street, Old Town Cottage puts you in one of the island's most desirable locations. You'll be close to restaurants, nightlife, historic attractions, shopping and waterfront activities while still having a private cottage to return to at the end of the day.
The cottage is also a wonderful option for extended stays in Key West. With a full kitchen, comfortable living space, two bedrooms, private laundry, outdoor space, outdoor shower and on site parking, it offers many of the conveniences that make a longer stay feel easy.
Whether you're planning a winter escape, an extended Key West getaway or simply looking for a comfortable home base in Old Town, Old Town Cottage gives you the opportunity to experience Key West beyond the typical vacation.
Make Old Town Cottage Your Home Away From Home.