Holmes Beach, FL

A Pirate's Dream

4 bedrooms 0 beds 4 baths 8 guests New

About the property

A Pirate’s Dream by AMI Locals 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 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

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 18, 2026$566.50Available7
May 19, 2026$566.50Available7
May 20, 2026$566.50Available7
May 21, 2026$566.50Available7
May 22, 2026$566.50Available7
May 23, 2026$585.04Not Available7
May 24, 2026$566.50Not Available7
May 25, 2026$566.50Not Available7
May 26, 2026$566.50Not Available7
May 27, 2026$568.56Not Available7
May 28, 2026$580.92Not Available7
May 29, 2026$716.88Not Available7
May 30, 2026$877.56Not Available7
May 31, 2026$724.09Not Available7
Jun 1, 2026$891.98Not Available7
Jun 2, 2026$938.33Not Available7
Jun 3, 2026$950.69Not Available7
Jun 4, 2026$958.93Not Available7
Jun 5, 2026$1,020.73Not Available7
Jun 6, 2026$956.87Not Available7
Jun 7, 2026$893.01Not Available7
Jun 8, 2026$903.31Not Available7
Jun 9, 2026$1,005.28Not Available7
Jun 10, 2026$1,010.43Not Available7
Jun 11, 2026$1,023.82Not Available7
Jun 12, 2026$1,039.27Not Available7
Jun 13, 2026$1,097.98Not Available7
Jun 14, 2026$1,092.83Not Available7
Jun 15, 2026$1,095.92Not Available7
Jun 16, 2026$1,110.34Not Available7
Jun 17, 2026$1,125.79Not Available7
Jun 18, 2026$1,138.15Not Available7
Jun 19, 2026$1,153.60Not Available7
Jun 20, 2026$1,127.85Not Available7
Jun 21, 2026$1,136.09Not Available7
Jun 22, 2026$1,141.24Not Available7
Jun 23, 2026$1,141.24Not Available7
Jun 24, 2026$1,144.33Not Available7
Jun 25, 2026$1,149.48Not Available7
Jun 26, 2026$1,156.69Not Available7
Jun 27, 2026$1,051.63Not Available7
Jun 28, 2026$1,071.20Not Available7
Jun 29, 2026$1,080.47Not Available7
Jun 30, 2026$1,094.89Not Available7
Jul 1, 2026$1,115.49Not Available7
Jul 2, 2026$1,203.04Not Available7
Jul 3, 2026$1,228.79Not Available7
Jul 4, 2026$1,215.40Available7
Jul 5, 2026$1,192.74Not Available7
Jul 6, 2026$1,184.50Not Available7
Jul 7, 2026$1,184.50Not Available7
Jul 8, 2026$1,184.50Not Available7
Jul 9, 2026$1,184.50Not Available7
Jul 10, 2026$1,184.50Not Available7
Jul 11, 2026$1,196.86Not Available7
Jul 12, 2026$1,191.71Not Available7
Jul 13, 2026$1,179.35Not Available7
Jul 14, 2026$1,177.29Not Available7
Jul 15, 2026$1,186.56Not Available7
Jul 16, 2026$1,199.95Not Available7
Jul 17, 2026$1,211.28Not Available7
Jul 18, 2026$1,043.39Not Available7
Jul 19, 2026$1,041.33Not Available7
Jul 20, 2026$1,030Not Available7
Jul 21, 2026$1,046.48Not Available7
Jul 22, 2026$1,024.85Not Available7
Jul 23, 2026$1,033.09Not Available7
Jul 24, 2026$1,030Not Available7
Jul 25, 2026$976.44Not Available7
Jul 26, 2026$964.08Not Available7
Jul 27, 2026$956.87Not Available7
Jul 28, 2026$930.09Not Available7
Jul 29, 2026$922.88Not Available7
Jul 30, 2026$914.64Not Available7
Jul 31, 2026$915.67Not Available7
Aug 1, 2026$867.26Not Available7
Aug 2, 2026$850.78Not Available7
Aug 3, 2026$833.27Not Available7
Aug 4, 2026$816.79Not Available7
Aug 5, 2026$810.61Not Available7
Aug 6, 2026$812.67Not Available7
Aug 7, 2026$815.76Not Available7
Aug 8, 2026$821.94Available7
Aug 9, 2026$752.93Not Available7
Aug 10, 2026$705.55Not Available7
Aug 11, 2026$690.10Not Available7
Aug 12, 2026$667.44Not Available7
Aug 13, 2026$660.23Not Available7
Aug 14, 2026$642.72Not Available7
Aug 15, 2026$843.57Available7
Aug 16, 2026$843.57Available7

Where you'll sleep

Amenities

Ocean view
Pool outdoor
Hot tub
Gym
Game Room
BBQ Area
Patio
Balcony

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Where you'll be

Holmes Beach, FL, 34217, US

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.