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Pirates Lookout

Almost beachfront







Pet friendly

Pirates Lookout

Welcome to Pirates Lookout, a slice of island paradise. This eclectic, surfer-chic carriage house is nestled on Anna Maria's North end.   

*Features include*

  • Chic and newly renovated carriage house with water views

  • Direct access to Bay beach

  • Kayak and SUP

  • 3 bedrooms and 2 full bathrooms

  • Sleeps six

  • Close proximity to shops and restaurants on Pine Avenue

  • Beach chairs, umbrella and cart

  • Pet friendly!

Perfect for families, couples, or close-knit friends, Pirates Lookout is a stylish and fun retreat for up to 6 guests. Ascend the outdoor stairs and enter the main living space that will beckon you with its cozy nooks and funky decor. The kitchen is fully remodeled and features coffee bar equipped with a Keurig and drip coffee maker. Take in glimpses of the water from the dining area and outdoor deck. 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 a full size washer and dryer as well as all the amenities you need to bring to the beach!  

Pirates Lookout offers all the modern amenities such as Wi-Fi, cable TV in each room, and tile throughout for a refreshing feel. Outside enjoy the private beach path, kayaks, SUP, and gas grill. 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 wall.

Pirates Lookout 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 front of this property is “Pirates Bay” - a stunning two bedroom waterfront pool house - although no amenities are shared when you rent Pirates Lookout, 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.

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 Lookout


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
Outdoor shower
Beach chairs
Beach umbrella
Beach wagon/cart
Beach towels
BBQ grill
Free parking on premises