Entire home
Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
Waterfront holiday home with private pool and kitchen
Photo gallery for Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream





Reviews
9.6 out of 10
Exceptional
4 bedrooms 3+ bathrooms Sleeps 8 2536 sq ft
Popular amenities
Explore the area

Holmes Beach, FL
- Place, Holmes Beach Beaches6 min walk
- Place, Manatee Public Beach8 min walk
- Place, West Coast Surf Shop8 min walk
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)32 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 King Bed
Loft
2 Single Bunk Beds
3 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Bathroom 3
Half Bathroom 1
Spaces
Deck or patio
Kitchen
Balcony
About this property
Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
A Pirate’s Dream by AMI Locals
Home in Holmes Beach, Florida
Highlights
• Private dock
• Private pool (Heated between Nov 1st- May 1st)
• 5-minute walk to the beach
• Outdoor kitchen
• Game room
A Pirate’s Dream by AMI Locals
221 N Harbor Dr
Holmes Beach, Florida
This grand, waterfront, four-bedroom, and three-and-a-half vacation home is A Pirate's Dream! Immerse yourself in the lore of piracy and the island history of Anna Maria. You can relax by the dock, which can accommodate vessels up to 38 ft, drop your kayak, paddleboard, and fishing line, set sail, or even look into boat rentals! You can also swim in the private pool or dine alfresco while savoring enchanting water views of the bay, vibrant sunrises, and sunsets.
A broad paver driveway leads to the graceful, Mediterranean-style front loggia, featuring columns, arches, and elaborate accents such as classic lantern-style chandeliers and Spanish wrought iron railings. The opulent interior spares no details; there are sizable picture windows framing canal and bay views for our guests to enjoy. Unwind on the plush cream-colored leather couches, engage in family board games, curl up with a good book, or stream your preferred shows or movies on the large wall-mounted Smart TV.
The spacious and bright gourmet chef's kitchen is perfect for entertaining guests. It features custom cabinetry, beautiful granite countertops, a breakfast bar with four stools, and stainless-steel appliances, including a gas stove with hood, convection oven, microwave, French door fridge with icemaker, dishwasher, and double basin sink. The kitchen also comes fully equipped with pots, pans, cookware, utensils, cutlery, dishware, glassware, a coffee maker, a kettle, a toaster, a blender, and a chef's knife block, among other things. Just adjacent is a large dining table that can seat six people comfortably. The modern geometric chandelier illuminates the dining area, while the outdoor dining table on the balcony provides cushioned seating for another six people.
Each bedroom has luxurious mattresses, sumptuous bedding, wall-mounted Smart TVs, ceiling fans, and bedside tables with reading lamps. The primary bedroom, located on the second floor, is particularly lavish with premium bedding and breathtaking water views from the balcony. Its attached bathroom boasts ample storage space and a grand walk-in shower adorned with marble tiles. The second bedroom features calming beach decor and a spacious ensuite bathroom with a walk-in closet and a gorgeous walk-in shower. The third and fourth bedrooms share a jack-n-jill bathroom with a walk-in shower, and the third bedroom also has a private balcony. The loft area is perfect for children, with two bunk beds and fun bean bag chairs to create a cozy oasis. There’s even a convenient laundry room with a state-of-the-art washer and dryer and a granite vanity laundry room sink.
Room Details
-Primary Bedroom, 2nd floor: King bed, Smart TV, balcony access, and an ensuite bathroom with walk-in shower
-Second bedroom, 3rd floor: King bed, Smart TV, and an ensuite bathroom with walk-in shower.
Third bedroom, 3rd floor: King bed, Smart TV, balcony access and jack-n-jill bathroom with walk-in shower
-Fourth Bedroom, 3rd floor: King bed, Smart TV, and jack-n-jill bathroom with walk-in shower
-Loft, 3rd floor: two sets of twin bunk beds, Smart TV, and balcony access
On the first floor is a game room with a lounge area with a sofa, a table, and chairs beside the ping pong table. It also features fun family games such as Connect Four and Corn Hole and a fridge and counter space that can be used as an extra space when using the poolside kitchen. This backyard boasts outstanding amenities, is surrounded by water and interlaced with canals, and host to many amazing sea creatures, including Loggerhead Turtles, Manatees, and dolphins. There is a free-form swimming pool, a sun shelf and a built-in picnic table, which is great for all ages, and the dock can accommodate vessels up to 38 feet. The outdoor kitchen is made of gorgeous stone and features a high-end grill and a large wall-mounted Smart TV. After dinner, you can gather your group for evening cocktails at the tiki bar, hoist the Jolly Roger, and drink some rum!
The beautiful white sand beaches of Anna Maria Island are less than a 5-minute walk away, and they are home to some of the most stunning seashells in all of Florida. It's quite common to see dolphins swimming and tourists enjoying a swim in the Gulf of Mexico. If you enjoy fishing, you can bring your gear and cast a line off the pier or rent a boat and venture out into deeper waters to reel in some fish. The free island trolley stop is also just a two-minute walk from your doorstep.
Longboat Key, Bradenton Beach, and Anna Maria Island have fantastic restaurants and beachside activities such as boat rentals, sunset cruises, jet ski, bike, paddleboard, scooter, and kayak rentals. Don't forget a trip to downtown Bradenton on the Manatee River with bars, dining, and Village of the Arts. The Village of the Arts is an eclectic live-work community of colorful historic cottages that house everything from award-winning restaurants to specialty shops, studios, healing arts, bakeries, and Bradenton’s best art galleries.
-
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.
Home in Holmes Beach, Florida
Highlights
• Private dock
• Private pool (Heated between Nov 1st- May 1st)
• 5-minute walk to the beach
• Outdoor kitchen
• Game room
A Pirate’s Dream by AMI Locals
221 N Harbor Dr
Holmes Beach, Florida
This grand, waterfront, four-bedroom, and three-and-a-half vacation home is A Pirate's Dream! Immerse yourself in the lore of piracy and the island history of Anna Maria. You can relax by the dock, which can accommodate vessels up to 38 ft, drop your kayak, paddleboard, and fishing line, set sail, or even look into boat rentals! You can also swim in the private pool or dine alfresco while savoring enchanting water views of the bay, vibrant sunrises, and sunsets.
A broad paver driveway leads to the graceful, Mediterranean-style front loggia, featuring columns, arches, and elaborate accents such as classic lantern-style chandeliers and Spanish wrought iron railings. The opulent interior spares no details; there are sizable picture windows framing canal and bay views for our guests to enjoy. Unwind on the plush cream-colored leather couches, engage in family board games, curl up with a good book, or stream your preferred shows or movies on the large wall-mounted Smart TV.
The spacious and bright gourmet chef's kitchen is perfect for entertaining guests. It features custom cabinetry, beautiful granite countertops, a breakfast bar with four stools, and stainless-steel appliances, including a gas stove with hood, convection oven, microwave, French door fridge with icemaker, dishwasher, and double basin sink. The kitchen also comes fully equipped with pots, pans, cookware, utensils, cutlery, dishware, glassware, a coffee maker, a kettle, a toaster, a blender, and a chef's knife block, among other things. Just adjacent is a large dining table that can seat six people comfortably. The modern geometric chandelier illuminates the dining area, while the outdoor dining table on the balcony provides cushioned seating for another six people.
Each bedroom has luxurious mattresses, sumptuous bedding, wall-mounted Smart TVs, ceiling fans, and bedside tables with reading lamps. The primary bedroom, located on the second floor, is particularly lavish with premium bedding and breathtaking water views from the balcony. Its attached bathroom boasts ample storage space and a grand walk-in shower adorned with marble tiles. The second bedroom features calming beach decor and a spacious ensuite bathroom with a walk-in closet and a gorgeous walk-in shower. The third and fourth bedrooms share a jack-n-jill bathroom with a walk-in shower, and the third bedroom also has a private balcony. The loft area is perfect for children, with two bunk beds and fun bean bag chairs to create a cozy oasis. There’s even a convenient laundry room with a state-of-the-art washer and dryer and a granite vanity laundry room sink.
Room Details
-Primary Bedroom, 2nd floor: King bed, Smart TV, balcony access, and an ensuite bathroom with walk-in shower
-Second bedroom, 3rd floor: King bed, Smart TV, and an ensuite bathroom with walk-in shower.
Third bedroom, 3rd floor: King bed, Smart TV, balcony access and jack-n-jill bathroom with walk-in shower
-Fourth Bedroom, 3rd floor: King bed, Smart TV, and jack-n-jill bathroom with walk-in shower
-Loft, 3rd floor: two sets of twin bunk beds, Smart TV, and balcony access
On the first floor is a game room with a lounge area with a sofa, a table, and chairs beside the ping pong table. It also features fun family games such as Connect Four and Corn Hole and a fridge and counter space that can be used as an extra space when using the poolside kitchen. This backyard boasts outstanding amenities, is surrounded by water and interlaced with canals, and host to many amazing sea creatures, including Loggerhead Turtles, Manatees, and dolphins. There is a free-form swimming pool, a sun shelf and a built-in picnic table, which is great for all ages, and the dock can accommodate vessels up to 38 feet. The outdoor kitchen is made of gorgeous stone and features a high-end grill and a large wall-mounted Smart TV. After dinner, you can gather your group for evening cocktails at the tiki bar, hoist the Jolly Roger, and drink some rum!
The beautiful white sand beaches of Anna Maria Island are less than a 5-minute walk away, and they are home to some of the most stunning seashells in all of Florida. It's quite common to see dolphins swimming and tourists enjoying a swim in the Gulf of Mexico. If you enjoy fishing, you can bring your gear and cast a line off the pier or rent a boat and venture out into deeper waters to reel in some fish. The free island trolley stop is also just a two-minute walk from your doorstep.
Longboat Key, Bradenton Beach, and Anna Maria Island have fantastic restaurants and beachside activities such as boat rentals, sunset cruises, jet ski, bike, paddleboard, scooter, and kayak rentals. Don't forget a trip to downtown Bradenton on the Manatee River with bars, dining, and Village of the Arts. The Village of the Arts is an eclectic live-work community of colorful historic cottages that house everything from award-winning restaurants to specialty shops, studios, healing arts, bakeries, and Bradenton’s best art galleries.
-
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Holmes Beach
Located in Holmes Beach, this holiday home is on the waterfront. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Holmes Beach, FL
What's nearby
- Holmes Beach Beaches - 6 min walk - 0.5 km
- Manatee Public Beach - 8 min walk - 0.7 km
- West Coast Surf Shop - 8 min walk - 0.7 km
- Bean Point Beach - 10 min drive - 5.8 km
- Anna Maria Beach - 11 min drive - 6.5 km
Getting around
Restaurants
- The Ugly Grouper - 14 min walk
- Anna Maria Island Beach Cafe - 8 min walk
- Dunkin' - 16 min walk
- Skinny's Place - 10 min walk
- Hurricane Hanks - 9 min walk
Frequently asked questions
About the host
Hosted by AMI Locals

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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