Flamingo Bay – Private Waterfront Paradise with Pool, Tiki Hut & Kayaks

Welcome to Flamingo Bay, where luxury, space, and jaw-dropping beauty come together on the sparkling open waters of Florida Bay in Islamorada. This massive private estate is a true showstopper, with three separate buildings designed for comfort, fun, and unforgettable memories. The main home features four spacious bedrooms, two full kitchens, an elevator, and a bright Florida sunroom that opens out to the pool. A separate two-bedroom, two-bath guest house with its own kitchenette offers the perfect retreat for friends or family, while the game house brings the entertainment with a pool table, dart board, TV, and bar area. Step outside and you’ll find paradise—your own private pool and hot tub, kayaks and paddleboards for exploring the bay, and a tiki hut at the end of the dock that feels like it was made for watching the most spectacular sunsets you’ve ever seen. Whether your days are spent fishing, boating, snorkeling, or simply soaking in the Keys sunshine, Flamingo Bay is more than a place to stay—it’s an 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.