$0
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Home in Holmes Beach, FL

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

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.

Where you’ll sleep

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

Amenities

Common Amenities

  • Wifi
  • Free parking
  • Outdoor dining area
  • Boat dock
  • Half bath
  • First aid kit
  • Life size games
  • Cornhole
  • Cooking basics
  • Wet bar
  • Beach access
  • Waterfront
  • Ensuite bathroom
  • Gym
  • Kayaks
  • Carbon monoxide detector
  • Smoke detector
  • Game Room
  • Fire extinguisher
  • Air conditioning
  • Bathtub
  • Ocean view
  • Kitchen
  • Balcony
  • Patio
  • Hair dryer
  • Heating
  • Ironing board
  • Toaster
  • Heated pool
  • Garden
  • Blender
  • Mini fridge
  • Hot water
  • Long term stays allowed
  • Baking sheet
  • Outdoor pool
  • Outdoor shower

Pool

  • Outdoor pool
  • Hot tub

Patio

  • Outdoor seating
  • BBQ Area
  • Outdoor kitchen

Balcony

  • Outdoor seating

Living Room

  • TV

Dining Room

  • Dining table

Kitchen

  • Oven
  • Stove
  • Microwave
  • Freezer
  • Fridge
  • Dishwasher
  • Dishes
  • Coffee maker
  • Kettle
  • Wine glasses

Game Room

  • Ping pong table

Bedroom 1

  • Bed linens
  • Ceiling fan

Ensuite Bathroom 1

  • Bath linens

Bedroom 2

  • Bed linens
  • Ceiling fan
  • TV

Ensuite Bathroom 2

  • Bath linens

Bedroom 3

  • Bed linens
  • TV

Bedroom 4

  • Bed linens

Bedroom 5

  • Bed linens
  • TV

Bathroom

  • Bath linens

Half Bath

  • Bath linens

Laundry Room

  • Washer
  • Dryer

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Where you’ll be

Holmes Beach, FL 34217, US

Holmes Beach, FL, US
27.5016429-82.7108363
Timezone: America/New_York

Restaurants

The Waterfront Restaurant

The 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.

Sandbar Seafood + Spirits

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.

Compass Hotel Anna Maria Sound by Margaritaville

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

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

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

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

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.

Mar Vista Dockside Restaurant & Pub

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.

Tide Tables Restaurant and Marina

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]

Attractions

Emerson Point Preserve

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 Access

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

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

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.

Robinson Preserve

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]

De Soto National Memorial

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]

Anna Maria Island Beach

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.

Holmes Beach

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.

Coquina Beach

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]

Things to know

Cancellation policy

Free cancellation up to 14 days before check-in. No refund after that.

Property rules

Pets not allowed

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Jul 15, 2026$739Not Available
Jul 16, 2026$740Not Available
Jul 17, 2026$838Not Available
Jul 18, 2026$764Not Available
Jul 19, 2026$666Not Available
Jul 20, 2026$665Not Available
Jul 21, 2026$688Not Available
Jul 22, 2026$778Not Available
Jul 23, 2026$783Not Available
Jul 24, 2026$828Not Available
Jul 25, 2026$816Not Available
Jul 26, 2026$767Not Available
Jul 27, 2026$755Not Available
Jul 28, 2026$734Not Available
Jul 29, 2026$771Not Available
Jul 30, 2026$774Not Available
Jul 31, 2026$810Not Available
Aug 1, 2026$824Not Available
Aug 2, 2026$728Not Available
Aug 3, 2026$720Not Available
Aug 4, 2026$711Not Available
Aug 5, 2026$731Not Available
Aug 6, 2026$717Not Available
Aug 7, 2026$793Not Available
Aug 8, 2026$724Available
Aug 9, 2026$595Available
Aug 10, 2026$567Available
Aug 11, 2026$567Available
Aug 12, 2026$567Available
Aug 13, 2026$567Available
Aug 14, 2026$596Available
Aug 15, 2026$802Available
Aug 16, 2026$793Available
Aug 17, 2026$790Available
Aug 18, 2026$786Available
Aug 19, 2026$782Available
Aug 20, 2026$784Available
Aug 21, 2026$790Available
Aug 22, 2026$567Available
Aug 23, 2026$567Available
Aug 24, 2026$567Available
Aug 25, 2026$567Available
Aug 26, 2026$567Available
Aug 27, 2026$567Available
Aug 28, 2026$567Available
Aug 29, 2026$567Available
Aug 30, 2026$634Available
Aug 31, 2026$631Available
Sep 1, 2026$602Available
Sep 2, 2026$631Available
Sep 3, 2026$706Available
Sep 4, 2026$709Available
Sep 5, 2026$712Available
Sep 6, 2026$618Available
Sep 7, 2026$618Available
Sep 8, 2026$618Available
Sep 9, 2026$618Available
Sep 10, 2026$618Available
Sep 11, 2026$618Available
Sep 12, 2026$584Not Available
Sep 13, 2026$609Not Available
Sep 14, 2026$604Not Available
Sep 15, 2026$604Not Available
Sep 16, 2026$604Not Available
Sep 17, 2026$605Not Available
Sep 18, 2026$567Not Available
Sep 19, 2026$667Available
Sep 20, 2026$665Available
Sep 21, 2026$665Available
Sep 22, 2026$665Available
Sep 23, 2026$665Available
Sep 24, 2026$666Available
Sep 25, 2026$668Available
Sep 26, 2026$567Available
Sep 27, 2026$567Available
Sep 28, 2026$567Available
Sep 29, 2026$567Available
Sep 30, 2026$567Available
Oct 1, 2026$567Available
Oct 2, 2026$567Available
Oct 3, 2026$567Available
Oct 4, 2026$567Available
Oct 5, 2026$567Available
Oct 6, 2026$569Available
Oct 7, 2026$592Available
Oct 8, 2026$639Available
Oct 9, 2026$637Available
Oct 10, 2026$657Not Available
Oct 11, 2026$657Not Available
Oct 12, 2026$650Not Available
Oct 13, 2026$643Not Available