Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
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!
- 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.
Our prices include all fees. No hidden fees.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Holmes Beach
Located in Holmes Beach, this vacation home is on the waterfront. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Traveling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.
Sarasota-Bradenton Intl. Airport (SRQ) - 40 min drive
Restaurants
Anna Maria Island Beach Cafe - 8 min walk
The Ugly Grouper - 14 min walk
Ginny's & Jane E's - 7 min drive
Smoqehouse - 5 min drive
Skinny's Place - 10 min walk
Frequently asked questions
Does Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream?
As of May 17, 2026, prices found for a 1-night stay for 2 adults at Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream on Aug 8, 2026 start from $737, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream pet-friendly?
No, pets are not allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream?
Check-in begins at 4:00 PM.
What time is check-out at Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream?
Check-out is at 10:00 AM.
Where is Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream located?
This family-friendly Holmes Beach vacation home is located on the waterfront, within a 10-minute walk of Bradenton Beach, Holmes Beach Beaches, and Manatee Public Beach. West Coast Surf Shop and AMI Paddleboard Adventures are also within 10 minutes.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Place was perfect for our friends and family getaway.. we saw manatees everyday by the dock, great fishing close by, nice quiet neighborhood..
Heather L.
Stayed 7 nights in Feb 2022
Response from VrboOwner on Sep 9, 2023
Thank you Heather for your recent stay with us at A Pirate's Dream! So happy to hear the home and location was a perfect fit for the fam. You were amazing to host and we hope to have the pleasure of having you again on your next island getaway.
Perfect location. Everything close, grocery, beach, pool. Watch the Manatee swim through the canal.
Fran H.
Stayed 7 nights in Oct 2022
Response from VrboOwner on Sep 9, 2023
Thank you for taking the time to share your experience with us, Fran. We are thrilled to hear you enjoyed the location, pool, and canal. We hope to host you again sometime soon!
The home is beautiful and location was perfect. Ample amount of room for all of our guests. It was nice getting the sunrise each morning with the view of the canal. We were able to see a manatee one day in the canal and tons of Huge finish swimming around the dock light at night. 10/10 would stay again!
Steve G.
Stayed 7 nights in May 2023
Response from VrboOwner on Sep 9, 2023
Thank you for taking the time to share your wonderful experience with us, Steve. We are glad you enjoyed your stay and look forward to hosting you again!
The house was very nice. there were some minor electrical challenges out on the doc and back patio but were able to work around them. We thoroughly enjoyed our time there. It was a nice space for kids and family connectedness. Everything was up to date and quite technologically advanced. The access to the bay, ocean and beaches were very convenient. We brought our 27 ft boat and it worked quite well. thanks for a great time!
Mike T.
Stayed 7 nights in Jul 2022
Response from VrboOwner on Sep 9, 2023
Mike, thank you for taking the time to share your experience with us. We are glad you enjoyed the home, dock, and location. We hope to host you again sometime in the future!
Our time at this wonderful vacation rental home was a blast! We vacation to Anna Maria every year with our best friends and our school-age kids, and this was our favorite place we have stayed EVER. Situated along a peaceful canal with a boat dock for us to tie up to, it offered something for everyone, from the kids to the teens and adults. We loved the views, the great pool and game room entertained the whole group for hours daily, and the indoor decor was just the right mix of comfy and chic. We fired up the outdoor kitchen for BBQs and beach days were easy with the Gulf of Mexico just a short stroll away. Overall, it was a top-notch stay, leaving us with memories we'll be talking about for ages. Thanks for having us! Highly recommend.
George N.
Stayed 1 night in Apr 2024
Response from VrboOwner on May 20, 2024
George, thank you for sharing your fantastic experience with us! We're thrilled to hear that your time at our vacation rental home was such a blast and that it exceeded your expectations as your favorite place you've stayed ever on Anna Maria Island.
It sounds like our property offered something for everyone in your group, from the peaceful canal views to the entertainment provided by the pool and game room. We're delighted that the indoor decor struck the right balance between comfort and chic, and that you were able to enjoy BBQs and beach days with ease.
Creating lasting memories for our guests is what we strive for, and we're thrilled to hear that your stay was top-notch and left you with memories to cherish for ages. Thank you for recommending us, and we would love to welcome you back for another unforgettable vacation in the future!
Verified
4/10 Poor
Mark R.
Sep 3, 2025
Liked: Check-in
Disliked: Communication, listing accuracy
We experienced several maintenance issues during our stay, which is unfortunately common. After contacting the management company, it took over a day and a half for someone to arrive, and they only addressed one of the three or four issues. They claimed they were only there to fix a doorknob. Despite multiple attempts to reach the management company, including sending pictures, they were very unresponsive. There are significant electrical problems, with fuses popping frequently – we couldn't even use the outdoor TV without shutting off something else.
Mark R.
Stayed 7 nights in Aug 2025
Response from VrboOwner on Sep 9, 2025
Thank you for taking the time to share your experience. I'm truly sorry to hear that your stay was impacted by maintenance issues and delays in communication. That’s not the level of service we strive to provide, and I understand how frustrating it must have been to deal with unresolved concerns during your visit.
Your feedback is incredibly valuable, and we’re taking it seriously. We’re actively working with our team to improve response times and ensure that all reported issues are addressed thoroughly and promptly. The electrical problems you mentioned are especially concerning, and we’ll be investigating them further to prevent future disruptions.
We appreciate your patience and hope you’ll consider giving us another opportunity to provide a better experience in the future.
We had a lovely time at this home. Don't sit on the fence on this one, it is just as pictured! Really close to everything and the beach is a SHORT walk, very easy to get to. It is well equipped. Wonderful outdoor area. We wish we would have had use of the fire pit as the evenings/nights were chilly. We had 6 adults and there was plenty of room for everyone. Only one real request, some extra blankets for sleeping. I know people staying in June, July and August would say "What" but we were at the end of May and were chilly in the bed.
Renee C.
Stayed 7 nights in May 2023
Response from VrboOwner on Oct 13, 2023
Thank you for taking the time to share your wonderful experience, Renee. We are glad you enjoyed the home, location, and outdoor area. We also appreciate your feedback regarding the extra blankets and will pass this on to our team. You were terrific guests, and we hope to welcome you back soon!
We loved Holmes Beach/Anna Maria Island! An amazing location for a vacation, especially if you are boaters. The bay, ICW and gulf -- all at your finger tips. The owners had their personal boat on their lift but we had plenty of space and water depth to dock our boat. The dock was spacious and equipped with water for washing down and a fish cleaning station. The house was awesome, roomy and clean with a beautiful view. We loved cooking dinners using the outdoor kitchen, listening to music and hanging by the pool. AMI was great to work with. We look forward to coming again next year! Thanks so much!
This house was absolutely beautiful. We stayed here with several members of our family, including children. Even though we had several people in one house, we did not feel as if we were crowded at all. House was stocked with kitchen supplies/appliances. The house was very clean. Check-in and check-out was also very easy. The house was perfect for everyone of all ages – kids & adults very much enjoyed the pool and dock. On a couple occasions we saw Manatees in the canal, which was really cool. The walk to the beach was not bad at all – just a couple minutes. Also, AMI Locals was super nice and responsive during our stay. We will be back.
Kate T.
Stayed 1 night in Nov 2021
Response from VrboOwner on Sep 9, 2023
Kate, thank you so much for the heart-warming review! We love hearing guests share their positive experiences and that you all enjoyed the space and pool area too! You were a great group to host and we look forward to your return.
Renta process was smooth. Upon arrival a few items were noted and forwarded to the property manager. AMI, the property management, was prompt to reply. Additional issues arose, again AMI replied promptly with a solution.
Each time these were property issues,
housekeeping issues, appliances didn't work, firepit not available as in listing & A/C pre-set control system.
The home served our family's needs.
Here is the list of problems. Unable to upload photos showing many of the issues.
1. Upon arrival,
A) Many utensils, glassware & mugs not all clean
B) Windows dirty
C) Stove hood full of grease
2. No bowls with lids
3. No products like Saran Wrap, foil, salt pepper
4. No Kleenex / tissues. We had to buy them.
5. Sink aerator / rubber piece was coming off.
6. Doorbell did not work.
7. Spotlight over grill did not work.
8. Cannot open many windows (handle missing). Makes it very warm when you want fresh air.
9. No screen on many windows.
10. Had issues with lighting in areas. Needed repair and instruction on how to operate a few switches. Management company could not give us a time as to when someone would come so we lost over half of one day waiting at house. This was incredibly frustrating and disappointing.
11. Slow internet – resolved on day 2
Julie B.
Stayed 7 nights in Feb 2023
Response from VrboOwner on Sep 9, 2023
Julie, thank you for taking the time to share your experience with us. Please allow us to apologize for the issues you mentioned during your stay, as we understand your frustration. Upon reviewing your account, we see our team was prompt and resolved all problems once you reported them. We regret we were unable to provide you with an estimated time of their arrival, but we are glad they were able to assist you. We hope you will return and stay with us again, giving us another opportunity to improve your experience.