$0
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Home in Holmes Beach, FL

A Pirate's Dream

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

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

Amenities

Common Amenities

  • Wifi
  • Free parking
  • Ocean view
  • Game Room
  • Patio
  • Balcony
  • Carbon monoxide detector
  • Smoke detector
  • Fire extinguisher
  • Air conditioning
  • Bathtub
  • Kitchen
  • Hair dryer
  • Heating
  • Ironing board
  • Toaster
  • Heated pool
  • Garden
  • Blender
  • Mini fridge
  • Hot water
  • Long term stays allowed
  • Baking sheet

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

Things to know

Cancellation policy

50% refund up to 30 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
Sep 20, 2026$567Not Available
Sep 21, 2026$567Not Available
Sep 22, 2026$567Not Available
Sep 23, 2026$567Not Available
Sep 24, 2026$567Not Available
Sep 25, 2026$567Not Available
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$567Available
Oct 7, 2026$567Available
Oct 8, 2026$567Available
Oct 9, 2026$567Available
Oct 10, 2026$575Not Available
Oct 11, 2026$567Not Available
Oct 12, 2026$567Not Available
Oct 13, 2026$567Not Available
Oct 14, 2026$567Not Available
Oct 15, 2026$567Not Available
Oct 16, 2026$599Not Available
Oct 17, 2026$603Available
Oct 18, 2026$567Available
Oct 19, 2026$567Available
Oct 20, 2026$567Available
Oct 21, 2026$721Available
Oct 22, 2026$732Available
Oct 23, 2026$737Available
Oct 24, 2026$731Available
Oct 25, 2026$720Available
Oct 26, 2026$711Available
Oct 27, 2026$708Available
Oct 28, 2026$710Available
Oct 29, 2026$714Available
Oct 30, 2026$720Available
Oct 31, 2026$567Available
Nov 1, 2026$567Available
Nov 2, 2026$567Available
Nov 3, 2026$567Available
Nov 4, 2026$567Available
Nov 5, 2026$606Available
Nov 6, 2026$642Available
Nov 7, 2026$668Available
Nov 8, 2026$627Available
Nov 9, 2026$570Available
Nov 10, 2026$575Available
Nov 11, 2026$575Available
Nov 12, 2026$567Available
Nov 13, 2026$592Available
Nov 14, 2026$587Available
Nov 15, 2026$567Available
Nov 16, 2026$567Available
Nov 17, 2026$567Available
Nov 18, 2026$567Available
Nov 19, 2026$568Available
Nov 20, 2026$664Available
Nov 21, 2026$1200Available
Nov 22, 2026$1196Not Available
Nov 23, 2026$1197Not Available
Nov 24, 2026$1203Not Available
Nov 25, 2026$1209Not Available
Nov 26, 2026$1210Not Available
Nov 27, 2026$1208Not Available
Nov 28, 2026$567Available
Nov 29, 2026$567Available
Nov 30, 2026$567Available
Dec 1, 2026$567Available
Dec 2, 2026$567Available
Dec 3, 2026$567Available
Dec 4, 2026$567Available
Dec 5, 2026$575Not Available
Dec 6, 2026$567Not Available
Dec 7, 2026$567Not Available
Dec 8, 2026$567Not Available
Dec 9, 2026$567Not Available
Dec 10, 2026$567Not Available
Dec 11, 2026$567Not Available
Dec 12, 2026$567Available
Dec 13, 2026$567Available
Dec 14, 2026$567Available
Dec 15, 2026$567Available
Dec 16, 2026$567Available
Dec 17, 2026$567Available
Dec 18, 2026$567Available
Dec 19, 2026$927Available