Holmes Beach, FL

A Pirate's Dream

4 bedrooms6 beds3.5 baths8 guestsNew

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!

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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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$852.84Not Available7
Jul 18, 2026$778.68Not Available7
Jul 19, 2026$671.56Not Available7
Jul 20, 2026$664.35Not Available7
Jul 21, 2026$687.01Not Available7
Jul 22, 2026$693.19Not Available7
Jul 23, 2026$698.34Not Available7
Jul 24, 2026$798.25Not Available7
Jul 25, 2026$822.97Not Available7
Jul 26, 2026$765.29Not Available7
Jul 27, 2026$752.93Not Available7
Jul 28, 2026$733.36Not Available7
Jul 29, 2026$727.18Not Available7
Jul 30, 2026$731.30Not Available7
Jul 31, 2026$809.58Not Available7
Aug 1, 2026$822.97Not Available7
Aug 2, 2026$728.21Not Available7
Aug 3, 2026$718.94Not Available7
Aug 4, 2026$710.70Not Available7
Aug 5, 2026$731.30Not Available7
Aug 6, 2026$724.09Not Available7
Aug 7, 2026$802.37Not Available7
Aug 8, 2026$723.06Available7
Aug 9, 2026$594.31Available7
Aug 10, 2026$566.50Available7
Aug 11, 2026$566.50Available7
Aug 12, 2026$566.50Available7
Aug 13, 2026$566.50Available7
Aug 14, 2026$566.50Available7
Aug 15, 2026$580.92Available7
Aug 16, 2026$793.10Available7
Aug 17, 2026$787.95Available7
Aug 18, 2026$784.86Available7
Aug 19, 2026$781.77Available7
Aug 20, 2026$783.83Available7
Aug 21, 2026$790.01Available7
Aug 22, 2026$566.50Available7
Aug 23, 2026$566.50Available7
Aug 24, 2026$566.50Available7
Aug 25, 2026$566.50Available7
Aug 26, 2026$566.50Available7
Aug 27, 2026$566.50Available7
Aug 28, 2026$566.50Available7
Aug 29, 2026$566.50Available7
Aug 30, 2026$621.09Available7
Aug 31, 2026$630.36Available7
Sep 1, 2026$600.49Available7
Sep 2, 2026$630.36Available7
Sep 3, 2026$705.55Available7
Sep 4, 2026$706.58Available7
Sep 5, 2026$711.73Available7
Sep 6, 2026$618Available7
Sep 7, 2026$618Available7
Sep 8, 2026$618Available7
Sep 9, 2026$618Available7
Sep 10, 2026$618Available7
Sep 11, 2026$618Available7
Sep 12, 2026$584.01Not Available7
Sep 13, 2026$589.16Not Available7
Sep 14, 2026$581.95Not Available7
Sep 15, 2026$603.58Not Available7
Sep 16, 2026$603.58Not Available7
Sep 17, 2026$604.61Not Available7
Sep 18, 2026$566.50Not Available7
Sep 19, 2026$667.44Available7
Sep 20, 2026$665.38Available7
Sep 21, 2026$665.38Available7
Sep 22, 2026$665.38Available7
Sep 23, 2026$665.38Available7
Sep 24, 2026$666.41Available7
Sep 25, 2026$668.47Available7
Sep 26, 2026$566.50Available7
Sep 27, 2026$566.50Available7
Sep 28, 2026$566.50Available7
Sep 29, 2026$566.50Available7
Sep 30, 2026$566.50Available7
Oct 1, 2026$566.50Available7
Oct 2, 2026$566.50Available7
Oct 3, 2026$566.50Available7
Oct 4, 2026$566.50Available7
Oct 5, 2026$566.50Available7
Oct 6, 2026$566.50Available7
Oct 7, 2026$590.19Available7
Oct 8, 2026$637.57Available7
Oct 9, 2026$629.33Available7
Oct 10, 2026$663.32Not Available7
Oct 11, 2026$664.35Not Available7
Oct 12, 2026$657.14Not Available7
Oct 13, 2026$649.93Not Available7
Oct 14, 2026$666.41Not Available7
Oct 15, 2026$673.62Not Available7

Amenities

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

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Where you'll be

Holmes Beach, FL, 34217, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

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.