Breathtaking Bayfront Retreat in Venetian Shores

Welcome to 116 Gulfside Drive — a breathtaking waterfront retreat in one of Islamorada’s most desirable neighborhoods. From the moment you walk through the door, panoramic bay views draw you in, flooding the home with natural light and capturing the beauty of the Florida Keys.

The main level offers bright, open living spaces designed for both style and comfort, along with three beautifully appointed bedrooms. Downstairs, a private apartment-style fourth bedroom with its own entrance is perfect for guests, in-laws, or anyone wanting extra privacy.

Step outside and discover where this home truly shines. Lush tropical landscaping frames a sparkling pool and spa, creating your own resort-like oasis. Multiple outdoor seating areas make it easy to relax, entertain, and savor the unforgettable sunsets over the bay.

For boaters, this property is pure paradise—tie up at your own floating dock or keep your vessel in a private slip at the Venetian Shores Marina, offering quick, bridge-free access to both the ocean and Florida Bay via Snake Creek.

Perfectly situated on a peaceful street yet just minutes from world-class fishing, dining, and shopping, this home delivers the very best of Islamorada living. Whether you’re setting out on the water, enjoying a cocktail at sunset, or simply unwinding in paradise, 116 Gulfside Drive offers a Keys experience you’ll never forget.

Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.