Welcome to Mermaid’s Bay Boutique Estate, an extraordinary bay-front retreat located in the heart of Islamorada. Set behind a private gate and spanning more than 3.5 acres of lush tropical landscape, this secluded estate offers a rare blend of privacy, history, and natural beauty, with over 300 feet of waterfront and sweeping views of the Florida Bay.

Originally built in the 1940s and lovingly preserved, Mermaid’s Bay is a hidden gem in the Keys. The estate includes three thoughtfully appointed homes, offering a total of eight bedrooms across the property. Each home is designed to provide its own sense of space and serenity, while still feeling connected to the overall estate. 

The spacious main house features four bedrooms, each with its own ensuite bathroom, and is ideal for gathering and entertaining. Two additional cottages, each with two bedrooms and one bathroom, offer charming, private accommodations for couples or smaller families. All three homes include private porches, individual yards, dedicated parking, and well-equipped kitchens, making it easy to settle in and feel at home. Details like outdoor grills, soft linens, and complimentary toiletries are provided to make your stay as seamless as it is comfortable.

Beyond the homes, the estate features a resort-style pool and spa, a private beach with hammocks and lounge chairs, a large protected boat basin, a small boat ramp and an array of amenities including kayaks, paddle-boards, and bikes. Whether you’re soaking in the sunset from the shoreline or heading out for a day on the water, Mermaid’s Bay offers the perfect backdrop for an unforgettable stay in the Florida Keys.

The estate can be rented as a whole or as individual units. To view each home separately, search by name on our website:

The Dock View House
The Bay View Cottage
The Garden View Cottage


Rentals are from Friday to Friday. Differing dates may be approved on a case-by-case basis. Availability and pricing shown in calendars or instant quotes are estimates only and subject to change. For the most accurate information, please contact us.