4 bedrooms
•
6 beds
•
3.5 bathrooms
•
8 guests
•
New
•
2536 sq. ft.
Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
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.
Bedroom 1
1 bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 bed
Bedroom 1
1 bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 bed
Be the first to review this place.
Holmes Beach, FL 34217, US
Holmes Beach, FL, US50% refund up to 30 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Sep 20, 2026 | $567 | Not Available |
| Sep 21, 2026 | $567 | Not Available |
| Sep 22, 2026 | $567 | Not Available |
| Sep 23, 2026 | $567 | Not Available |
| Sep 24, 2026 | $567 | Not Available |
| Sep 25, 2026 | $567 | Not Available |
| Sep 26, 2026 | $567 | Available |
| Sep 27, 2026 | $567 | Available |
| Sep 28, 2026 | $567 | Available |
| Sep 29, 2026 | $567 | Available |
| Sep 30, 2026 | $567 | Available |
| Oct 1, 2026 | $567 | Available |
| Oct 2, 2026 | $567 | Available |
| Oct 3, 2026 | $567 | Available |
| Oct 4, 2026 | $567 | Available |
| Oct 5, 2026 | $567 | Available |
| Oct 6, 2026 | $567 | Available |
| Oct 7, 2026 | $567 | Available |
| Oct 8, 2026 | $567 | Available |
| Oct 9, 2026 | $567 | Available |
| Oct 10, 2026 | $575 | Not Available |
| Oct 11, 2026 | $567 | Not Available |
| Oct 12, 2026 | $567 | Not Available |
| Oct 13, 2026 | $567 | Not Available |
| Oct 14, 2026 | $567 | Not Available |
| Oct 15, 2026 | $567 | Not Available |
| Oct 16, 2026 | $599 | Not Available |
| Oct 17, 2026 | $603 | Available |
| Oct 18, 2026 | $567 | Available |
| Oct 19, 2026 | $567 | Available |
| Oct 20, 2026 | $567 | Available |
| Oct 21, 2026 | $721 | Available |
| Oct 22, 2026 | $732 | Available |
| Oct 23, 2026 | $737 | Available |
| Oct 24, 2026 | $731 | Available |
| Oct 25, 2026 | $720 | Available |
| Oct 26, 2026 | $711 | Available |
| Oct 27, 2026 | $708 | Available |
| Oct 28, 2026 | $710 | Available |
| Oct 29, 2026 | $714 | Available |
| Oct 30, 2026 | $720 | Available |
| Oct 31, 2026 | $567 | Available |
| Nov 1, 2026 | $567 | Available |
| Nov 2, 2026 | $567 | Available |
| Nov 3, 2026 | $567 | Available |
| Nov 4, 2026 | $567 | Available |
| Nov 5, 2026 | $606 | Available |
| Nov 6, 2026 | $642 | Available |
| Nov 7, 2026 | $668 | Available |
| Nov 8, 2026 | $627 | Available |
| Nov 9, 2026 | $570 | Available |
| Nov 10, 2026 | $575 | Available |
| Nov 11, 2026 | $575 | Available |
| Nov 12, 2026 | $567 | Available |
| Nov 13, 2026 | $592 | Available |
| Nov 14, 2026 | $587 | Available |
| Nov 15, 2026 | $567 | Available |
| Nov 16, 2026 | $567 | Available |
| Nov 17, 2026 | $567 | Available |
| Nov 18, 2026 | $567 | Available |
| Nov 19, 2026 | $568 | Available |
| Nov 20, 2026 | $664 | Available |
| Nov 21, 2026 | $1200 | Available |
| Nov 22, 2026 | $1196 | Not Available |
| Nov 23, 2026 | $1197 | Not Available |
| Nov 24, 2026 | $1203 | Not Available |
| Nov 25, 2026 | $1209 | Not Available |
| Nov 26, 2026 | $1210 | Not Available |
| Nov 27, 2026 | $1208 | Not Available |
| Nov 28, 2026 | $567 | Available |
| Nov 29, 2026 | $567 | Available |
| Nov 30, 2026 | $567 | Available |
| Dec 1, 2026 | $567 | Available |
| Dec 2, 2026 | $567 | Available |
| Dec 3, 2026 | $567 | Available |
| Dec 4, 2026 | $567 | Available |
| Dec 5, 2026 | $575 | Not Available |
| Dec 6, 2026 | $567 | Not Available |
| Dec 7, 2026 | $567 | Not Available |
| Dec 8, 2026 | $567 | Not Available |
| Dec 9, 2026 | $567 | Not Available |
| Dec 10, 2026 | $567 | Not Available |
| Dec 11, 2026 | $567 | Not Available |
| Dec 12, 2026 | $567 | Available |
| Dec 13, 2026 | $567 | Available |
| Dec 14, 2026 | $567 | Available |
| Dec 15, 2026 | $567 | Available |
| Dec 16, 2026 | $567 | Available |
| Dec 17, 2026 | $567 | Available |
| Dec 18, 2026 | $567 | Available |
| Dec 19, 2026 | $927 | Available |