Welcome to A Pirate's Dream
Bring your boat! You will have a jolly good time!
The island lifestyle will be hard to leave once you indulge in a stay at this luxury canal front retreat in the heart of Holmes Beach. This 4 bedroom beauty boasts a coastal vibe that will spoil even the most design-oriented of guests. A Pirate's Dream offers balconies on all levels to start each morning with a warm cup of coffee as you look out to the canal and the view of the open bay where you can watch manatees and dolphin play. Views of the beautifully illuminated Skyway bridge can be seen from the large waterfront, entertainment patio and upper deck. When the sun heats up, everyone can head to the private, heated pool and lounge in bliss while the kids play in the refreshing water. Drop a line right off the dock and enjoy some Florida fishing! Preparing poolside snacks and gourmet meals will be easy in the fully equipped outdoor kitchen, bar and grill area, complete with 65 inch TV. Everyone will love eating al fresco on the patio!
After watching the sunset from your favorite spot, gather around the patio or let your competitive side out with a ping-pong tournament!
A Pirate's Dream offers the most stunning views of the open bay from the water front out door kitchen, deck and all balcony levels. Enjoy incredible amenities, plenty of beach gear and a private boat slip that accommodates vessels up to 35 feet!
Home Layout:
Main Floor:
Bedroom #1 - King with Ensuite Bathroom
Second Floor:
Bedroom #2 King - With Ensuite Bathroom
Bedroom #3 King - Shares Jack n Jill Ensuite Bathroom
Bedroom #4 King - Shares Jack n Jill Ensuite Bathroom
Bonus Room- 2 Twin over Twin Bunk Beds
*Outdoor Shower
Home Features:
• A Pirate's Dream offers bayside views with a quick four
minute walk to the other side of the island, on the sugar
sand beach
• two minute walk to the free, island trolley for access to
the entire island
• Ample seating all over with six person high top tables for
out door dining on the water front patio and the second
floor balcony, a perfect beach home for entertaining!
• Main living room has a wet bar with gorgeous views
• Large flat screen Smart TVs throughout the home
• Luxurious master suites, all with King beds and en suit
bathrooms, showers and walk-in closets
• Loft area with four twin bunk beds
• Outdoor heated shower by the pool
Come and Enjoy this Boater's Dream and Waterfront Paradise!
**Boat Slip-Accommodates up to 35 foot Vessel**
*Please note: 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.
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 to a respectful level 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/or termination of your rental agreement without refund.
Vacation Rental Certificate # VRC21-000086
May 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
June 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 |
July 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | |||||
03 | 04 | 05 | 06 | 07 | 08 | 09 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
31 |
August 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | |
07 | 08 | 09 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 | 31 |
September 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | ||||
04 | 05 | 06 | 07 | 08 | 09 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 |
October 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
November 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | ||
06 | 07 | 08 | 09 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 |
December 2022 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | ||||
04 | 05 | 06 | 07 | 08 | 09 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 | 31 |
January 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
February 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 |
March 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 | 31 |
April 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 |
May 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | |
07 | 08 | 09 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 | 31 |
June 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | ||||
04 | 05 | 06 | 07 | 08 | 09 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 |
July 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
August 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | ||
06 | 07 | 08 | 09 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 | 31 |
September 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | |||||
03 | 04 | 05 | 06 | 07 | 08 | 09 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
October 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
November 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 |
December 2023 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | |||||
03 | 04 | 05 | 06 | 07 | 08 | 09 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
31 |
January 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | |
07 | 08 | 09 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 | 31 |
February 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | ||||
04 | 05 | 06 | 07 | 08 | 09 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 |
March 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | |||||
03 | 04 | 05 | 06 | 07 | 08 | 09 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
31 |
April 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | |
07 | 08 | 09 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 |
May 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 | 31 |
June 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 |
July 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | |
07 | 08 | 09 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 | 31 |
August 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | ||||
04 | 05 | 06 | 07 | 08 | 09 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 | 31 |
September 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 |
October 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | ||
06 | 07 | 08 | 09 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 | 31 |
November 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | |||||
03 | 04 | 05 | 06 | 07 | 08 | 09 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
December 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
January 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 | 31 |
February 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 |
March 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
April 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | ||
06 | 07 | 08 | 09 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 |
Amazing home and to fish right off the dock was great. The manatee would swim around the inlet so that was a wonderful surprise. Our first time to Anna Maria and will come back! This area is not commercialized but the family loved riding the bikes everywhere.
- Margie , Posted: 08/02/2021
Wonderful Dream Home not just for Pirates
I don’t know where to begin! The 3 level views were spectacular! The swimming pool with the ever changing colorful night lights added to our fabulous swim experience. They had activity things downstairs for the kids, beach chairs, sand toys among pool floaters. We loved having our meals outside at very level of the home. We loved morning meals off the kitchen and evening meals by the pool down next to the pool. It was quite an impressive home. Several grandkids loved the pool and time spent there better than Disney! Thank you AMI for helping us find this gem and helping with the pool specifics!- Michele W from Papillion, Posted: 01/03/2022
Nice grand house n location with views
We enjoyed this bayfront home w enough room for my grandkids n family Ami locals is lovely n accommodating as well- Mary D from Massachusetts , Posted: 02/07/2022
Select your Arrival and Departure dates to see Detailed Pricing