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Pirates Bay








Pet friendly

Pirates Bay

Beachfront pool home on the secluded and desirable North end of Anna Maria just steps to the Rod and Reel Pier!

*Features include*

  • Charming and renovated ground level beachfront home

  • Private saltwater heated pool with full water views

  • Direct access to Bay beach

  • Kayak and SUP

  • Master suite with king bed and ensuite bath

  • Guest bedroom with king bed

  • Close proximity to shops and restaurants on Pine Avenue

  • Beach chairs, umbrella, cooler

  • Pet friendly!

Welcome to Pirates Bay, a stunning 2 bedroom, 2 bath vacation home designed for the perfect beach getaway. Nestled on the sought-after North Shore, this vintage coastal home seamlessly blends modern amenities with the laid-back charm of beachfront living.

Step inside to find a fully equipped kitchen with both a Keurig and drip coffee maker, for your morning caffeine fix. The open floor plan encompasses a great room and dining area, all 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 home features two king bedrooms and two full baths - the master suite treats you to an ensuite bathroom for added privacy. You will find plenty of amenities, including a laundry area with full-sized washer and dryer, gas grill, games, books, and cable TV throughout.

The highlight of Pirates Bay 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 Bay 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. In back of this property is a unique 3 bedroom carriage house, "Pirates Lookout", although no amenities are shared and the private heated pool is all yours when you rent Pirates Bay. You can rent both units for a 5-bedroom family retreat, ideal 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 2 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 Bay


AMENITIES (scroll through)
Ground level home
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 Bay