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.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Anna Maria Pirates Den

Show Prices
Certificate of Excellence
Book on TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Enter dates for best prices
powered by PriceFinder
Prices from our online travel partners are not available
We can't find prices for this hotel
Our online travel partners don't provide prices for this accommodation, but we can search other options in Holmes Beach
Check In Check Out
Show Prices
Management photos
Anna Maria Pirates Den
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"containerClass":null,"scriptFlags":null}
Add Photo Write a Review

165 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
There are newer reviews for Anna Maria Pirates Den
See the most recent reviews
Showing 164: English reviews
Sobieski, Wisconsin, United States
Level Contributor
7 reviews
common_n_hotel_reviews_1bd8 5 helpful votes
Reviewed 26 February 2016

If you want to be just steps across the street from the beach with a Publix right around the corner ... have a nice warm pool and a phenomenally clean, perfect apartment... Then Pirate's Den is the spot for you! You feel like you are visiting family because Kathy, Al and Vicky are so warm and friendly - whatever you... More 

Thank christina390
vickykay8364, Owner at Anna Maria Pirates Den, responded to this review

We are so glad you enjoyed your stay and look forward to your return!! Thank you for your kind words. -vicky and Kevin mcphail More 

Moncton, Canada
1 review
Reviewed 23 February 2016

Love love love this spot! Stayed from Feb 9 to Feb 18, 2016 - the weather was perfect, the island is amazing - we walked most of it :-) you can hear the surf from bed...the apartments are comfortable and well provisioned couldn't ask for anything more and we didn't !!!!!! I'm pining already and want to come back :(... More 

Thank Charmyra
vickykay8364, Owner at Anna Maria Pirates Den, responded to this review

We are so glad you enjoyed your stay and our beautiful island. We look forward to your return to the pirates den! Hope to see you again soon-Vicky and Kevin McPhail More 

Champlin, Minnesota
Level Contributor
72 reviews
23 hotel reviews
common_n_hotel_reviews_1bd8 20 helpful votes
Reviewed 24 January 2016

This is a great place for families. It is less than 5 minutes from the beach and very close to the "commercial district" in AMI. The pool is nice. The WI-Fi was disappointing but you don't go to FL for the Wi-Fi. They even let us use towels for the beach.

Thank Cesamos
vickykay8364, Owner at Anna Maria Pirates Den, responded to this review

Your kind words are appreciated and glad you enjoyed your stay! Each of our units have individual wifi and so sorry it was acting up, our local provider has corrected the issue with your unit! Hope to see you back at the pirates den.-vicky More 

Sarasota, Florida
1 review
Reviewed 23 January 2016

The Pirates Den was like going to a family cottage by the beach. First of all its family owned, which is awesome. We were greeted by Vicky and her mother who went above and beyond to make our stay the best it could be.. And it was. In my opinion, it's in the best location on the island, short walk... More 

Thank Brian H
vickykay8364, Owner at Anna Maria Pirates Den, responded to this review

We are so glad you enjoyed your stay and we will be honored to help you and your family celebrate your special day! See you soon!-vicky More 

Bradenton, Florida
1 review
Reviewed 18 January 2016

By far our favorite place to stay on Anna Maria Island yet! Vicky couldn't have been more helpful and went above and beyond to accommodate our needs. Words can't explain what wonderful customer service means. We were greeted by Vicky's mother to show us our place and make us feel at home...it's so nice to see a family run resort... More 

Thank Audra L
vickykay8364, Owner at Anna Maria Pirates Den, responded to this review

We are so glad you enjoyed your stay! Thank you for your kind words and we look for a rd to your return! Vicky and Kevin More 

Provincetown, Massachusetts
1 review
Reviewed 16 December 2015

We have recently returned from another stay at the Pirates Den and once again have enjoyed every moment of our stay. The apt is comfy and has everything that we could ever need...just as if we were at home. The unit is clean and the location is perfect. The beach is just across the street and the Publix grocery store... More 

Thank joady b
Level Contributor
17 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
Reviewed 2 December 2015 via mobile

Pirates Den is a wonderful, small, family run resort. We stayed for 3 nights. Vicky was a pleasure from the first phone call. We brought our 21 ft boat and our dog. Vicky made room for us to park our boat/trailer on site. Our well behaved dog was welcome throughout the beautifully landscaped resort...including the pool area. Our 1 bedroom... More 

Thank Teresa C
Edinburgh, United Kingdom
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
Reviewed 26 October 2015

Our family of 5 spent one night at Pirates Den in Oct & we had a fantastic time. Vicky was very helpful & always replied quickly to emails . The beach is a few minutes walk away and is stunning. We appreciated being able to borrow chairs from the garage at Pirates Den. Vicky's parents were so friendly and happy... More 

1 Thank Yvonne D
Burnside, Kentucky
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
Reviewed 6 October 2015

It was within walking distance to the beach, the owner and everybody else there are very friendly, they make you feel right at home, their very clean and organized and I would totally stay there next time we come back to Anna Maria island

1 Thank kayce j
Leicester, United Kingdom
Level Contributor
52 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 22 helpful votes
Reviewed 13 August 2015 via mobile

Just got back from a lovely 2 nights here at Pirates Den. We booked with Vicky and had regular contact which is reassuring. On arrival we had a warm welcome from Vicky's parents Kathy & Al. Kathy was lovely and showed us up to apartment 4. She was happy to help and answer any questions. You can access the garage... More 

4 Thank Louise B

103 photos of this hotel

Traveller photos: See what travellers like you saw

All Traveller Photos (63)
Hotel & Grounds (2)
Pool/Beach Area (14)
Room/Suite (12)
Bathroom (1)
View from Room (5)
Dining (4)
Other (25)

Management photos: Courtesy of the property manager

All Management Photos (40)
Room/Suite (22)
Pool/Beach Area (3)
View from Room (1)
Hotel & Grounds (6)
Bathroom (6)
Other (2)
Check In Check Out
Hotels you might also like...
Also consider these accommodations in or near Holmes Beach
1.0 km away
Cedar Cove Resort & Cottages
Cedar Cove Resort & Cottages
#2 of 15 in Holmes Beach
870 reviews
2.5 km away
Silver Surf Gulf Beach Resort
Silver Surf Gulf Beach Resort
#3 of 12 in Bradenton Beach
544 reviews
2.4 km away
An Island Getaway at Palm Tree Villas
Show Prices
Show Prices
Show Prices
1.3 km away
Anna Maria Island Dream Inn
Anna Maria Island Dream Inn
#11 of 12 in Bradenton Beach
137 reviews
2.6 km away
Queen's Gate Resort
Queen's Gate Resort
#7 of 12 in Bradenton Beach
162 reviews
3.4 km away
Haleys Motel and Resort
Haleys Motel and Resort
#5 of 15 in Holmes Beach
271 reviews
Show Prices
Show Prices
Show Prices


  • Pool
  • Free Parking
  • Beachfront
About the property
  • Beachfront
  • Pets Allowed ( Dog / Pet Friendly )
Things to do
  • Pool
Room types
  • Suites
  • Kitchenette
In your room
  • Air Conditioning
  • Refrigerator in room
  • Free Parking
Official Description (provided by the hotel)
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". ... more   less 

Additional Information about Anna Maria Pirates Den

Address: 3501 Gulf Dr, Holmes Beach, Anna Maria Island, FL 34217-2028
Region: United States > Florida > Anna Maria Island > Holmes Beach
Price Range: $107 - $248 (Based on Average Rates for a Standard Room)
Number of rooms: 6
Also Known As:
Anna Maria Pirates Den Hotel Holmes Beach
Hotel Anna Maria Island
Resort Anna Maria Island
Anna Maria Pirates Den Anna Maria Island/Holmes Beach, Florida
Hotel Style:
#1 Best Value Hotel in Holmes Beach
#3 Family Hotel in Holmes Beach
#3 On the Beach Hotel in Holmes Beach
#6 Romantic Hotel in Holmes 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

Questions & Answers

Here's what travellers have asked, with answers from Anna Maria Pirates Den staff and other travellers.
1 question
Ask a question
6 months ago

See all questions (1)

Questions? Get answers from Anna Maria Pirates Den staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travellers prefer

“All room very clean with the coastal décor with a bit of Key West flare.”
 of 5 bubbles davidrZ5493OY, 16 Aug 2016 | Read review
“The upper level units are more modern than the lower level units.”
 of 5 bubbles lisarodriguez1840, 5 Aug 2016 | Read review
“We stayed in the upstairs apartment and from the deck and out the bedroom window you can get a little glimpse of the beach.”
 of 5 bubbles A5860MYkimberlys, 29 Jun 2016 | Read review
“Everything looked great !”
 of 5 bubbles Mamamia15, 30 May 2016 | Read review
“Unit 1 has a partial view of the beach down the street. Unit 2 overlooks the pool. Both upstairs units.”
 of 5 bubbles luv2cruise2013, 30 May 2016 | Read review
5 of 5