Holmes Beach, FL

A Pirate's Dream

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8 guests
4 bedrooms
4 bathrooms
2536 sqft

A Pirate’s Dream by AMI Locals

  • Ocean view
  • Fire place
  • Balcony
8 guests
4 bedrooms
4 bathrooms
2536 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • 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.

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) AvailabilityMin Stay (nights)
Feb 16, 2026$695Available3
Feb 17, 2026$695Available3
Feb 18, 2026$695Available3
Feb 19, 2026$695Available3
Feb 20, 2026$695Available3
Feb 21, 2026$695Available3
Feb 22, 2026$695Available3
Feb 23, 2026$695Available3
Feb 24, 2026$695Available3
Feb 25, 2026$695Available3
Feb 26, 2026$695Available3
Feb 27, 2026$695Available3
Feb 28, 2026$695Available3
Mar 1, 2026$695Available3
Mar 2, 2026$695Available3
Mar 3, 2026$695Available3
Mar 4, 2026$695Available3
Mar 5, 2026$695Available3
Mar 6, 2026$695Available3
Mar 7, 2026$695Not Available3
Mar 8, 2026$695Not Available3
Mar 9, 2026$695Not Available3
Mar 10, 2026$695Not Available3
Mar 11, 2026$695Not Available3
Mar 12, 2026$695Not Available3
Mar 13, 2026$695Not Available3
Mar 14, 2026$695Not Available3
Mar 15, 2026$695Not Available3
Mar 16, 2026$695Not Available3
Mar 17, 2026$695Not Available3
Mar 18, 2026$695Not Available3
Mar 19, 2026$695Not Available3
Mar 20, 2026$695Not Available3
Mar 21, 2026$695Available3
Mar 22, 2026$695Available3
Mar 23, 2026$695Available3
Mar 24, 2026$695Available3
Mar 25, 2026$695Available3
Mar 26, 2026$695Available3
Mar 27, 2026$695Available3
Mar 28, 2026$695Not Available3
Mar 29, 2026$695Not Available3
Mar 30, 2026$695Not Available3
Mar 31, 2026$695Not Available3
Apr 1, 2026$695Not Available3
Apr 2, 2026$695Not Available3
Apr 3, 2026$695Not Available3
Apr 4, 2026$695Not Available3
Apr 5, 2026$695Not Available3
Apr 6, 2026$695Not Available3
Apr 7, 2026$695Not Available3
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Apr 10, 2026$695Not Available3
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Apr 12, 2026$695Not Available3
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Apr 14, 2026$695Not Available3
Apr 15, 2026$695Not Available3
Apr 16, 2026$695Not Available3
Apr 17, 2026$695Not Available3
Apr 18, 2026$695Available3
Apr 19, 2026$695Available3
Apr 20, 2026$695Available3
Apr 21, 2026$695Available3
Apr 22, 2026$695Available3
Apr 23, 2026$695Available3
Apr 24, 2026$695Available3
Apr 25, 2026$695Not Available3
Apr 26, 2026$695Not Available3
Apr 27, 2026$695Not Available3
Apr 28, 2026$695Not Available3
Apr 29, 2026$695Not Available3
Apr 30, 2026$695Not Available3
May 1, 2026$695Not Available3
May 2, 2026$695Available3
May 3, 2026$695Available3
May 4, 2026$695Available3
May 5, 2026$695Available3
May 6, 2026$695Available3
May 7, 2026$695Available3
May 8, 2026$695Available3
May 9, 2026$695Available3
May 10, 2026$695Available3
May 11, 2026$695Available3
May 12, 2026$695Available3
May 13, 2026$695Available3
May 14, 2026$695Available3
May 15, 2026$695Available3
May 16, 2026$695Available3
May 17, 2026$695Available3

Top notch amenities

GUEST FAVORITES

Ocean view
Fire place
Patio
Balcony
Outdoor seating
Bath linens
Bed linens
Body soap
Air conditioning

Where you'll sleep



Explore Holmes Beach, FL

Immerse yourself in the coastal elegance of Anna Maria Island, where the soft sands of Manatee Public Beach are steps away for morning strolls along the Gulf. This prime location offers easy access to the pristine Anna Maria Island Beach and the historic Star Fish Company, perfect for sampling fresh seafood in a waterfront setting. Explore the scenic trails of Robinson Preserve or visit the adjacent Publix Super Market to gather artisanal ingredients

Things to know

Here are some things which you should know before booking A Pirate's Dream

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Prime Vacations - Anna Maria’s standard cancellation policy.