A Pirate's Dream

Average Rating

Address: 221 N Harbor Dr Location: Holmes Beach Type: House
4 Bedrooms 4 Full, 1 Half Bathrooms Sleeps 12 No

• 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 SmartTV.

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 SmartTVs, 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 SmartTV. 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.

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  • Air Conditioning
  • Beach Towels Included
  • Bed Linens
  • Clothes Hangers
  • Dryer
  • Guest Essentials
  • Hair Dryer
  • Heating
  • Hot Water
  • Private Entrance
  • Towels
  • Washer
  • Wireless Internet

  • Balcony
  • BBQ Area
  • Grill
  • Heated Pool
  • Outdoor Kitchen
  • Patio
  • Private Boat Dock
  • Private Pool
  • Tiki Bar

Fun & Entertainment
  • Cornhole
  • Game Room
  • Ping Pong Table
  • Satellite or Cable
  • Smart TV
  • Television

Home Safety
  • Carbon Monoxide Detector
  • Fire Extinguisher
  • Security Camera
  • Smoke Detector

  • Full Kitchen
  • Living Room

  • Coffee Maker
  • Dishes & Silverware
  • Microwave
  • Oven
  • Refrigerator
  • Stove

  • Anna Maria Island
  • Less than a 5-minute walk to the beach
  • On Anna Maria Island
  • Residential Street
  • Water Views
  • Waterfront
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