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.
Exterior
1 full bed
Patio
1 full bed
Living Room
1 full bed
Kitchen
1 full bed
Game Room
2 full beds
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Exterior
1 full bed
Patio
1 full bed
Living Room
1 full bed
Kitchen
1 full bed
Game Room
2 full beds
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
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Holmes Beach, FL 34217, US
Holmes Beach, FL, USThe Waterfront in Wildwood, NJ is a casual waterfront dining destination featuring fresh cuisine, happy hour specials, and live entertainment, with stunning views of Otten's Harbor from its upstairs deck—the perfect spot for sunset dining and special celebrations.
Savor fresh, wild-caught seafood like chargrilled octopus and grouper at Sandbar Seafood + Spirits, Anna Maria Island's iconic beachfront gem. Dine toes-in-the-sand with breathtaking Gulf sunsets and a rustic coastal vibe.
Savor fresh-caught seafood, woodfire-grilled steaks, and juicy burgers at Floridays Woodfire Grill & Bar, the Compass Hotel's casual waterfront gem with stunning bayside views and a laid-back Florida vibe. Pair your meal with Margaritaville cocktails during happy hour at the adjacent Compass Bar & Chill.
The Ugly Grouper is a laid-back outdoor seafood restaurant on Anna Maria Island famous for its crispy grouper tacos, fresh catches, and lively island atmosphere complete with live music and games every night.
Shore Longboat Key captivates with creative seafood and coastal American dishes like Key West shrimp risotto and Thai curry mussels, served in a mid-century al-fresco setting on the water. Cool vibes, signature cocktails, and fresh, flavorful eats make it a beachside must.
Anna Maria Island Beach Cafe is a casual beachfront dining destination famous for its all-you-can-eat pancakes and fresh seafood, offering Gulf views, live music, and a laid-back island atmosphere perfect for breakfast, lunch, or dinner.
Swordfish Grill is a laid-back waterfront seafood restaurant in Cortez, Florida, where you can dock your boat and enjoy fresh Gulf catches while watching fishing boats unload their daily haul. The tiki-covered deck offers live music, great views of Sarasota Bay, and a fun, casual atmosphere that locals and visitors love.
Discover Mar Vista Dockside Restaurant & Pub, a waterfront gem on Longboat Key blending Old Florida charm with fresh, locally-sourced seafood under century-old buttonwood trees. Dine on the private beach or covered patio, savoring Gulf-inspired dishes amid stunning bay views.
Nestled in historic Cortez Fishing Village on the Intracoastal Waterway, Tide Tables serves ultra-fresh seafood cut daily from the docks, alongside burgers and bites, with stunning waterfront views, dolphin sightings, and laid-back outdoor picnic seating.[1][2][3]
Discover ancient temple mounds built over 4,500 years ago, hike scenic trails through tropical hammocks, kayak mangrove estuaries, and spot vibrant wildlife at Emerson Point Preserve. Nature lovers, history buffs, and outdoor adventurers will love this hidden coastal gem.[1][2][3]
Bean Point Beach offers a serene escape at Anna Maria Island's northern tip, where soft white sand meets turquoise waters with stunning views of Tampa Bay and the Sunshine Skyway Bridge—perfect for nature lovers and those seeking a quieter alternative to crowded beaches.
Manatee Public Beach offers a perfect blend of relaxation and recreation with pristine white sand, calm Gulf waters, and excellent amenities like volleyball courts, playgrounds, and beachside dining—ideal for families, active adventurers, and anyone seeking a complete beach day experience.
G.T. Bray Park is Manatee County's premier recreational destination featuring world-class pickleball courts, diverse sports facilities, playgrounds, and scenic trails—perfect for athletes, families, and anyone seeking outdoor fun in one comprehensive venue.
Discover Robinson Preserve's lush mangrove tunnels, canopy walkways, and 53-foot observation tower with sweeping Tampa Bay views, perfect for kayaking amid dolphins and manatees or family hikes. Nature lovers, adventurers, and outdoor families will love this coastal gem.[1][2][4]
Discover De Soto National Memorial, a hidden gem blending 16th-century explorer history with serene nature trails, ranger-led kayak tours, and living history at Camp Uzita. History buffs, families, and outdoor adventurers will love its free, uncrowded charm.[1][2][3][5]
Unwind on Anna Maria Island Beach's pristine, sugar-white sands, where clear turquoise waters invite kayaking, paddleboarding, and dolphin spotting amid Old Florida charm. Beach lovers, families, and outdoor adventurers will cherish its serene sunsets and wildlife encounters.
Discover playful dolphins and crystal-clear waters on this beginner-friendly 4-hour snorkeling adventure from Holmes Beach, complete with manatee sightings and island vibes. Perfect for families, nature lovers, and first-time explorers seeking unforgettable aquatic thrills.
Discover Coquina Beach's pristine white sands, calm waters teeming with dolphins, manatees, and sea turtles, perfect for kayaking, paddleboarding, or shell hunting. Families and couples love its safe, uncrowded vibes and stunning sunsets on Anna Maria Island.[1][2][4]
Free cancellation up to 14 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 |
|---|---|---|
| Jul 15, 2026 | $739 | Not Available |
| Jul 16, 2026 | $740 | Not Available |
| Jul 17, 2026 | $838 | Not Available |
| Jul 18, 2026 | $764 | Not Available |
| Jul 19, 2026 | $666 | Not Available |
| Jul 20, 2026 | $665 | Not Available |
| Jul 21, 2026 | $688 | Not Available |
| Jul 22, 2026 | $778 | Not Available |
| Jul 23, 2026 | $783 | Not Available |
| Jul 24, 2026 | $828 | Not Available |
| Jul 25, 2026 | $816 | Not Available |
| Jul 26, 2026 | $767 | Not Available |
| Jul 27, 2026 | $755 | Not Available |
| Jul 28, 2026 | $734 | Not Available |
| Jul 29, 2026 | $771 | Not Available |
| Jul 30, 2026 | $774 | Not Available |
| Jul 31, 2026 | $810 | Not Available |
| Aug 1, 2026 | $824 | Not Available |
| Aug 2, 2026 | $728 | Not Available |
| Aug 3, 2026 | $720 | Not Available |
| Aug 4, 2026 | $711 | Not Available |
| Aug 5, 2026 | $731 | Not Available |
| Aug 6, 2026 | $717 | Not Available |
| Aug 7, 2026 | $793 | Not Available |
| Aug 8, 2026 | $724 | Available |
| Aug 9, 2026 | $595 | Available |
| Aug 10, 2026 | $567 | Available |
| Aug 11, 2026 | $567 | Available |
| Aug 12, 2026 | $567 | Available |
| Aug 13, 2026 | $567 | Available |
| Aug 14, 2026 | $596 | Available |
| Aug 15, 2026 | $802 | Available |
| Aug 16, 2026 | $793 | Available |
| Aug 17, 2026 | $790 | Available |
| Aug 18, 2026 | $786 | Available |
| Aug 19, 2026 | $782 | Available |
| Aug 20, 2026 | $784 | Available |
| Aug 21, 2026 | $790 | Available |
| Aug 22, 2026 | $567 | Available |
| Aug 23, 2026 | $567 | Available |
| Aug 24, 2026 | $567 | Available |
| Aug 25, 2026 | $567 | Available |
| Aug 26, 2026 | $567 | Available |
| Aug 27, 2026 | $567 | Available |
| Aug 28, 2026 | $567 | Available |
| Aug 29, 2026 | $567 | Available |
| Aug 30, 2026 | $634 | Available |
| Aug 31, 2026 | $631 | Available |
| Sep 1, 2026 | $602 | Available |
| Sep 2, 2026 | $631 | Available |
| Sep 3, 2026 | $706 | Available |
| Sep 4, 2026 | $709 | Available |
| Sep 5, 2026 | $712 | Available |
| Sep 6, 2026 | $618 | Available |
| Sep 7, 2026 | $618 | Available |
| Sep 8, 2026 | $618 | Available |
| Sep 9, 2026 | $618 | Available |
| Sep 10, 2026 | $618 | Available |
| Sep 11, 2026 | $618 | Available |
| Sep 12, 2026 | $584 | Not Available |
| Sep 13, 2026 | $609 | Not Available |
| Sep 14, 2026 | $604 | Not Available |
| Sep 15, 2026 | $604 | Not Available |
| Sep 16, 2026 | $604 | Not Available |
| Sep 17, 2026 | $605 | Not Available |
| Sep 18, 2026 | $567 | Not Available |
| Sep 19, 2026 | $667 | Available |
| Sep 20, 2026 | $665 | Available |
| Sep 21, 2026 | $665 | Available |
| Sep 22, 2026 | $665 | Available |
| Sep 23, 2026 | $665 | Available |
| Sep 24, 2026 | $666 | Available |
| Sep 25, 2026 | $668 | 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 | $569 | Available |
| Oct 7, 2026 | $592 | Available |
| Oct 8, 2026 | $639 | Available |
| Oct 9, 2026 | $637 | Available |
| Oct 10, 2026 | $657 | Not Available |
| Oct 11, 2026 | $657 | Not Available |
| Oct 12, 2026 | $650 | Not Available |
| Oct 13, 2026 | $643 | Not Available |