A Pirate’s Dream

Welcome to A Pirate’s Dream, a grand waterfront retreat that perfectly blends coastal elegance with island adventure on beautiful Anna Maria Island. This four bedroom, three and a half bath vacation home plus loft is designed for families and groups seeking both relaxation and excitement. Located just a five-minute walk from the beach, this Mediterranean inspired home features a private dock, a heated pool, and spectacular bay and canal views, creating a luxurious setting for your next island getaway. Highlights • 5-minute walk to Holmes Beach • 4 Bedrooms / 3.5 Bathrooms • 4 King beds, 4 Twin beds • Private dock • Heated private pool with sun shelf and picnic table • Outdoor kitchen with grill, TV, and bar • Game room with ping pong, Connect Four, and Cornhole • Balcony water views and multiple lounge areas • 4 Parking spaces Relax and unwind in your own tropical paradise, surrounded by tranquil canals and swaying palms. Enjoy the heated pool featuring a built in picnic table and sun shelf, perfect for cooling off or lounging in the Florida sunshine. The outdoor kitchen boasts a high end grill, stone finishes, and a TV, while the tiki bar sets the scene for memorable evenings with friends and family. With a private dock that accommodates boats up to 38 feet, you can kayak, paddleboard, or watch for dolphins and manatees right from your backyard. Inside, Mediterranean elegance meets modern comfort. The open concept living room invites you to relax on plush leather sofas while streaming your favorite shows on the large TV. The chef’s kitchen is fully equipped with stainless steel appliances, granite countertops, custom cabinetry, and a breakfast bar with seating. Gather around the dining table for six or take your meals outdoors on the balcony to enjoy the view. Each bedroom provides the perfect retreat with luxurious bedding, TVs, and ceiling fans. The primary suite on the second floor offers a king bed, balcony access, and a spa-inspired ensuite bathroom with a marble walk-in shower. The second bedroom features a king bed and private ensuite, while the third and fourth bedrooms share a jack-and-jill bathroom with a walk-in shower. The third bedroom also includes a private balcony. Upstairs, the loft with two twin bunk sets and a Smart TV creates a cozy hideaway for kids or teens. Room Details • Primary Bedroom (2nd floor): King bed, balcony, ensuite bathroom with walk-in shower • Second Bedroom (3rd floor): King bed, ensuite bathroom with walk-in shower • Third Bedroom (3rd floor): King bed, balcony, jack-and-jill bathroom with walk-in shower • Fourth Bedroom (3rd floor): King bed, jack-and-jill bathroom with walk-in shower • Loft (3rd floor): Two sets of twin bunk beds, balcony access The first-floor game room is perfect for family fun, featuring a ping pong table, lounge area, and an extra fridge for poolside drinks. The laundry room includes a washer, dryer, and granite utility sink for convenience. Located near restaurants such as Skinny’s Place inc. and Hurricane Hanks, or close to Publix Super Market, this waterfront home keeps you close to Anna Maria Island’s best dining, shopping, and outdoor experiences while maintaining the privacy of your own tropical oasis. From morning coffee on the balcony to sunset cocktails by the tiki bar, A Pirate’s Dream offers the ultimate Anna Maria Island vacation rental experience. Embrace the laid-back luxury of island life, where every day feels like a treasure waiting to be discovered. Book your stay today and set sail on your perfect coastal escape! - 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Garage is off-limits to any vehicles, including Golf Carts No Pets are allowed in this home These premises are monitored by video surveillance in select exterior areas. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise respectful during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions, including fines and termination of your rental agreement without a refund.