We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Anna Maria Pirates Den

3501 Gulf Dr, Holmes Beach, Anna Maria Island, FL 34217-2028
Contact accommodation for availability.
There are similar hotels available.
View all
Traveller (111)
Room & Suite (71)
Pool & Beach (26)
Payments made by partners impact the order of prices displayed. Room types may vary.


#2 of 15 hotels in Holmes Beach
Travellers' Choice
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".
Read more
Full view
Property amenities
Free parking
Outdoor pool
Heated pool
Pets Allowed ( Dog / Pet Friendly )
Non-smoking hotel
Self-serve laundry
Room features
Air conditioning
Private balcony
Flatscreen TV
Room types
Non-smoking rooms
Family rooms
Good to know
Family Resort
Hidden Gem
280Reviews9Q+A45Room tips
Traveller rating
  • 251
  • 22
  • 2
  • 3
  • 2
Time of year
Traveller type
Selected filters
  • Filter
  • English
Popular mentions
bjs119 wrote a review Jan 2020
Michigan58 contributions24 helpful votes
We stayed in unit 1 with two bedrooms, kitchen, dining and bath. It is on the front with a screened patio and a side door that leads right to the pool. In spite of a couple of days of -15 below average temps, we sat by the pool with excellent wind protection and great afternoon sun. We walked to the beach each evening for an amazing sunset, found many great restaurants. We loved Skinny’s for a cheeseburger and a beer. We really liked Eat Here for dinner. Had a great lunch with a French craft beer and excellent rose’ at My Ami. Enjoyed shopping at “the old IGA.” Can’t explain, just go there. Our apartment was very clean and nice, bed very comfortable, and most important, Vicki and Kevin are great hosts!
Read more
Date of stay: January 2020Trip type: Travelled as a couple
Linda G wrote a review Oct 2019
Tampa, United States2 contributions
Love Pirates Den and the family who owns it. Vicky takes care of every detail to make your stay perfect. Beautiful accomodations, everything you need for the beach and pool is provided, and always greeted by a smiling face. We will be returning for another vacation!
Read more
Date of stay: September 2019
Sleep Quality
brianfish31 wrote a review Oct 2019
4 contributions2 helpful votes
I could never get tired of staying here. I the owners would ever let me and my wife rent a unit long term we would move in yesterday. The owners of the place keep it to perfection. They continue to make changes and upgrades to make sure it will continue to be the best. They never leave a stone unturned. Durning our last stay my wife lost her phone. The owners walked the property with us in hope of finding it. After not finding it we had to order a new one. It was sent via fedex. FedEx called the office and let them know the time of delivery on Saturday. Vicki the called me to let us know to relax go to breakfast if the phone comes they would sign for it. We actually all sat out side waiting for it.... getting caught up on life with some of our favorite people. As always staying here is like staying with family except you come and go as you please. Every time we stay here its simply perfect... sun rain it doesnt matter the location provides easy access to all the island has to offer. We cant wait to schedule our next stay at The Pirates Den.....
Read more
Date of stay: October 2019Trip type: Travelled as a couple
mamma5665 wrote a review Oct 2019
Bensenville, Illinois3 contributions1 helpful vote
This resort has very friendly owners that make you feel like part of the family as soon as you arrive. It is a short distance from bars and restauraunts so it is quiet and peaceful. It has a beautifully landscaped pool area with aheated pool. Just steps from a beautiful white sandy beach that stretches the length of the entire island. I highly recommend Anna Maria Pirates Den.
Read more
Date of stay: October 2019Trip type: Travelled with family
Nancy lamb wrote a review Sep 2019
2 contributions1 helpful vote
Love this place....guests are treated like family Highly recommend!!!!! Great pool very close to the beach. Convenient to restaurants and shopping: owners are very helpful with anything you may need. Great location,
Read more
Date of stay: October 2018
Sleep Quality
1 Helpful vote
Response from Vicky M, Owner at Anna Maria Pirates Den
Responded 19 Sep 2019
Thank you so much for your review! We look forward to seeing you soon at the PIRATES DEN!
Read more
anna maria pirates den hotel holmes beach, hotel anna maria island, resort anna maria island
United StatesFloridaAnna Maria IslandHolmes Beach
Is This Your Tripadvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing
Frequently Asked Questions about Anna Maria Pirates Den
Which popular attractions are close to Anna Maria Pirates Den?
Nearby attractions include Manatee Public Beach (0.4 km), Bradenton Beach City Pier (0.3 km), and Bob Brown Art (0.1 km).
What are some of the property amenities at Anna Maria Pirates Den?
Some of the more popular amenities offered include a pool, free parking, and self serve laundry.
Which room amenities are available at Anna Maria Pirates Den?
Top room amenities include a kitchenette, air conditioning, and a flat screen TV.
Is parking available at Anna Maria Pirates Den?
Yes, free parking is available to guests.
What are some restaurants close to Anna Maria Pirates Den?
Conveniently located restaurants include Holy Cow Ice Cream & Other Cool Stuff, Old Hamburg Schnitzelhaus, and Peach's Restaurants.
Are there opportunities to exercise at Anna Maria Pirates Den?
Yes, guests have access to a pool during their stay.
Are pets allowed at Anna Maria Pirates Den?
Yes, pets are typically allowed, but it's always best to call ahead to confirm.
Are there any historical sites close to Anna Maria Pirates Den?
Many travellers enjoy visiting De Soto National Memorial (7.1 km).