A Pirate's Dream
A Pirate’s Dream by AMI Locals
- Ocean view
- Fire place
- Balcony
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Flexible check-in & out
Check-in after 4:00 PM • Check-out before 10:00 AM
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Easy cancellation
About this property
A Pirate’s Dream by AMI Locals 221 N Harbor Dr, Holmes Beach, Florida Welcome to A Pirate’s Dream by AMI Locals, 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 by AMI Locals 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 This home is managed by AMI Locals, an Anna Maria Island property management company. 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.
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Feb 16, 2026 | $695 | Available | 3 |
| Feb 17, 2026 | $695 | Available | 3 |
| Feb 18, 2026 | $695 | Available | 3 |
| Feb 19, 2026 | $695 | Available | 3 |
| Feb 20, 2026 | $695 | Available | 3 |
| Feb 21, 2026 | $695 | Available | 3 |
| Feb 22, 2026 | $695 | Available | 3 |
| Feb 23, 2026 | $695 | Available | 3 |
| Feb 24, 2026 | $695 | Available | 3 |
| Feb 25, 2026 | $695 | Available | 3 |
| Feb 26, 2026 | $695 | Available | 3 |
| Feb 27, 2026 | $695 | Available | 3 |
| Feb 28, 2026 | $695 | Available | 3 |
| Mar 1, 2026 | $695 | Available | 3 |
| Mar 2, 2026 | $695 | Available | 3 |
| Mar 3, 2026 | $695 | Available | 3 |
| Mar 4, 2026 | $695 | Available | 3 |
| Mar 5, 2026 | $695 | Available | 3 |
| Mar 6, 2026 | $695 | Available | 3 |
| Mar 7, 2026 | $695 | Not Available | 3 |
| Mar 8, 2026 | $695 | Not Available | 3 |
| Mar 9, 2026 | $695 | Not Available | 3 |
| Mar 10, 2026 | $695 | Not Available | 3 |
| Mar 11, 2026 | $695 | Not Available | 3 |
| Mar 12, 2026 | $695 | Not Available | 3 |
| Mar 13, 2026 | $695 | Not Available | 3 |
| Mar 14, 2026 | $695 | Not Available | 3 |
| Mar 15, 2026 | $695 | Not Available | 3 |
| Mar 16, 2026 | $695 | Not Available | 3 |
| Mar 17, 2026 | $695 | Not Available | 3 |
| Mar 18, 2026 | $695 | Not Available | 3 |
| Mar 19, 2026 | $695 | Not Available | 3 |
| Mar 20, 2026 | $695 | Not Available | 3 |
| Mar 21, 2026 | $695 | Available | 3 |
| Mar 22, 2026 | $695 | Available | 3 |
| Mar 23, 2026 | $695 | Available | 3 |
| Mar 24, 2026 | $695 | Available | 3 |
| Mar 25, 2026 | $695 | Available | 3 |
| Mar 26, 2026 | $695 | Available | 3 |
| Mar 27, 2026 | $695 | Available | 3 |
| Mar 28, 2026 | $695 | Not Available | 3 |
| Mar 29, 2026 | $695 | Not Available | 3 |
| Mar 30, 2026 | $695 | Not Available | 3 |
| Mar 31, 2026 | $695 | Not Available | 3 |
| Apr 1, 2026 | $695 | Not Available | 3 |
| Apr 2, 2026 | $695 | Not Available | 3 |
| Apr 3, 2026 | $695 | Not Available | 3 |
| Apr 4, 2026 | $695 | Not Available | 3 |
| Apr 5, 2026 | $695 | Not Available | 3 |
| Apr 6, 2026 | $695 | Not Available | 3 |
| Apr 7, 2026 | $695 | Not Available | 3 |
| Apr 8, 2026 | $695 | Not Available | 3 |
| Apr 9, 2026 | $695 | Not Available | 3 |
| Apr 10, 2026 | $695 | Not Available | 3 |
| Apr 11, 2026 | $695 | Not Available | 3 |
| Apr 12, 2026 | $695 | Not Available | 3 |
| Apr 13, 2026 | $695 | Not Available | 3 |
| Apr 14, 2026 | $695 | Not Available | 3 |
| Apr 15, 2026 | $695 | Not Available | 3 |
| Apr 16, 2026 | $695 | Not Available | 3 |
| Apr 17, 2026 | $695 | Not Available | 3 |
| Apr 18, 2026 | $695 | Available | 3 |
| Apr 19, 2026 | $695 | Available | 3 |
| Apr 20, 2026 | $695 | Available | 3 |
| Apr 21, 2026 | $695 | Available | 3 |
| Apr 22, 2026 | $695 | Available | 3 |
| Apr 23, 2026 | $695 | Available | 3 |
| Apr 24, 2026 | $695 | Available | 3 |
| Apr 25, 2026 | $695 | Not Available | 3 |
| Apr 26, 2026 | $695 | Not Available | 3 |
| Apr 27, 2026 | $695 | Not Available | 3 |
| Apr 28, 2026 | $695 | Not Available | 3 |
| Apr 29, 2026 | $695 | Not Available | 3 |
| Apr 30, 2026 | $695 | Not Available | 3 |
| May 1, 2026 | $695 | Not Available | 3 |
| May 2, 2026 | $695 | Available | 3 |
| May 3, 2026 | $695 | Available | 3 |
| May 4, 2026 | $695 | Available | 3 |
| May 5, 2026 | $695 | Available | 3 |
| May 6, 2026 | $695 | Available | 3 |
| May 7, 2026 | $695 | Available | 3 |
| May 8, 2026 | $695 | Available | 3 |
| May 9, 2026 | $695 | Available | 3 |
| May 10, 2026 | $695 | Available | 3 |
| May 11, 2026 | $695 | Available | 3 |
| May 12, 2026 | $695 | Available | 3 |
| May 13, 2026 | $695 | Available | 3 |
| May 14, 2026 | $695 | Available | 3 |
| May 15, 2026 | $695 | Available | 3 |
| May 16, 2026 | $695 | Available | 3 |
| May 17, 2026 | $695 | Available | 3 |
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