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Pirates Bounty








Pet friendly

Pirates Bounty

The ultimate 5 bedroom beachfront retreat on the secluded and desirable North end of Anna Maria. Only steps to the Rod and Reel Pier!

*Features include*

  • Amazing beachfront retreat with private pool

  • 5 total bedrooms and 4 full bathrooms

  • 2 bedrooms located in beachfront ground level home

  • 3 bedrooms in the newly renovated carriage house with water views

  • Direct access to Bay beach

  • Kayaks and SUPs

  • Close proximity to shops and restaurants on Pine Avenue

  • Beach chairs, umbrella and cart

  • Pet friendly!

Pirates Bounty is an exclusive waterfront escape on Anna Maria Island! This 5-bedroom, 4-bath vacation rental offers panoramic water views, a private heated pool, and serene outdoor deck for a truly memorable stay. Set up as 2 private units - a 2 bedroom waterfront retreat with 3 bedroom carriage house right behind - Pirates Bounty offers togetherness and privacy for your extended family and friends getaway.

First, step inside the waterfront home known as “Pirates Bay” to find a fully equipped kitchen and open floor plan. The spacious great room and dining area are adorned with floor-to-ceiling windows, capturing every bit of the spectacular Bay views. In the evening, experience the magic of the moonlit bay and the distant glow of the Sunshine Skyway bridge - an idyllic scene to unwind and reflect.

This portion of the rental property features two king bedrooms and two full baths, one ensuite. You will find plenty of amenities, including a laundry area with full-sized washer and dryer, games, books, Wi-Fi, cable TV in each room, and tile throughout for a refreshing feel.

Next, ascend the outdoor stairs and head up to the 3 bedroom carriage house “Pirates Lookout”. The living space will beckon you with its cozy nooks and funky decor. The kitchen is fully remodeled and features a coffee bar equipped with a Keurig and drip coffee maker. On this main elevated level you will also find a comfy king bedroom and full bath accessible from the hallway.

Downstairs you will find 2 additional queen guest bedrooms connected by a Jack and Jill full bathroom. A small spiral staircase leads the way from inside the home, or you may also enter through the ground level door inside the garage. In the garage there is another full size washer and dryer as well as all the amenities you need to bring to the beach!

The true highlight of Pirates Bounty is the expansive waterfront pool deck that leads to a sandy beach and calm waters perfect for wading or swimming. Take one of the provided kayaks or stand up paddleboards out for a little exploring. It's important to note that due to recent hurricanes, the sandy beach in front of the seawall has changed and may continue to change with the tides. At high tide the water will come up to the deck.  

Pirates Bounty is conveniently located steps from the Rod and Reel Pier. Indulge yourself with refreshing drinks, fresh seafood, fishing, and dolphin or manatee spotting from the pier. This 5-bedroom family retreat is your ideal spot for larger gatherings and shared memories.

We generally require a minimum stay of 7 nights with Saturday check-in during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!

We are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing.


2 pets maximum unless granted an exception. Weight limit of 75 lbs maximum per pet.

Due to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted:  

  • Pit Bull 

  • Akita 

  • Rottweiler 

  • German Shepherd 

  • Siberian Husky 

  • Malamute 

  • Doberman Pinscher 

  • Chows 

  • Any Wolf-dog hybrid 

  • Any other dog that has been known to have bitten anyone

Anna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music is allowed during these hours along with any other noise which may disturb the neighbors.

We do not accept reservations from any guests under the age of 25. The primary guest will be required to provide proof of age and must occupy the rental home for the duration of the reservation.

This home provides off-street parking for up to 4 vehicles. Please note there is no parking allowed in the garage.

A minimum deposit of 25% of the total rental fee is due at the time of booking. If the arrival date is within 60 days, payment is due in full. For information regarding our cancellation policy, please click here.


Pirates Bounty


AMENITIES (scroll through)
Basic soap
Starter toilet paper
Starter paper towels
Linens provided
Towels provided
Hair dryer
Washing machine
Clothes dryer
Wireless internet
Standard coffee maker
Heated pool
Private pool
Outdoor shower
Beach chairs
Beach umbrella
Beach wagon/cart
Beach towels
Sun loungers
BBQ grill
Free parking on premises


Pirates Bounty