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Anna Maria Pirates Den

Traveler (97)
Room & Suite (64)
Pool & Beach (18)
Certificate of Excellence


Certificate of Excellence
Anna Maria Pirates Den is a small family run resort located on gulf drive in Holmes Beach. We have four individually decorated 2 bedroom apartments and 2 one bedroom cottages. Enjoy the island way of life, sun, beach, and most of all relaxation. Swim in the warm waters of the Gulf of Mexico and walk any of the seven miles of sandy beaches and of course if you walk too far you can always catch the free trolley back to your fully equipped apartment. The island described by the English Daily Mail newspaper as "tranquil Florida, as it used to be, just beaches, pelicans and palm trees".
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Property amenities
Free parking
Heated pool
Non-smoking hotel
Outdoor pool
Pets Allowed ( Dog / Pet Friendly )
Self-Serve Laundry
Room features
Air conditioning
Refrigerator in room
Family Rooms
Non-smoking rooms
Good to know
Hidden Gem
Centrally Located
Hotel links
Visit hotel website


Full view
75Somewhat walkable
Grade: 75 out of 100
13Restaurantswithin 0.3 miles
4Attractionswithin 0.3 miles
44Room tips
Traveler rating
  • 230
  • 21
  • 2
  • 3
  • 2
Time of year
Traveler type
  • Filter
  • English
Popular mentions
We’ve spent the past 4 weeks at the Pirates Den and have had a fantastic time. This was our third stay here and we highly recommend it. The resort is close to the beach, has a wonderful (warm) pool, is pet friendly, and very nice accommodations. Thank you to the great hosts for
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Thank you, Kevin, Vicki, and Kathy for providing a wonderful vacation spot! Everything was perfect....the rooms, the cleanliness, and definitely the pool. We spent a lot of time at the pool and made many friends at your establishment. We were minutes from the beach and enjoyed
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We stayed this weekend at Pirates Den and we couldn’t be happier! We were even able to bring our dog. Staff was great, place was wonderful and in the perfect location! The pool was great for our young kids and we were able to take a short walk to the beach! We will definitely be
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What a fantastic place, across the street from the beach! The owners and operators are wonderful, welcoming, and friendly. After one stay we already feel like family. We are looking forward to our next trip back!
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This was our third visit to the Pirates Den and every time we stay longer and bring more people with us. The unit this year accommodated two couples easier and even had room for our dog. The area is within walking distance to the beach and local stores and restaurants. We were
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Album Categories
All photosTravelerRoom & SuitePool & BeachDining
Photo provided by managementAnna Maria Pirates Den
Cottage 6
The most romatic sunsets
Sunset at Pirates Den
How close to the beach ? One , two blocks ?
One block
0 votes
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We have reservations to stay at Pirates Dem. Please provide me with their phone number.
0 votes
Do you have availability for July 9th through the 12th
yes we do, please call Pirates Den 9417784368, thank you-vicky
0 votes
Hi! Do you have any availability June 17th through June 22nd? And what are your rates?
we do have availability.bplease call the pirates den 9417784368 for rates, how many people? thank you -vicky PIRATES DEN
0 votes
Please post your prices from April 18-25.
"close to the beach, comfortable, Pool"
"Apartment 1has a private screened in porch"
"We had a two bedroom, two bathroom apartment and it was great!"
"The owner will help you decide what is a nice room for your needs. She is very knowledgeable about what you will need."
"All rooms have kitchens and living rooms. The upstairs units have pitched ceilings"
anna maria pirates den hotel holmes beachhotel anna maria islandresort anna maria island
United StatesFloridaAnna Maria IslandHolmes Beach
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