The Lookout

Perfectly positioned directly on the water, The Lookout offers a private waterfront pool, an incredible covered gazebo lounge, and sweeping bay views that make every moment feel like a postcard.

*Features Include*

• Direct beachfront location

• Private waterfront swimming pool

• Huge covered gazebo outdoor living area

• Outdoor dining and lounge spaces overlooking the bay

• Bayfront loungers with umbrellas

• Outdoor firepit gathering area

• New top-to-bottom designer renovation

• Three bedrooms, two full bathrooms

• Washer and dryer

• Minutes to Bean Point and Pine Avenue

Welcome to The Lookout, a stunning bayfront retreat on coveted North Shore Drive in Anna Maria. Fresh from a top-to-bottom designer renovation, this beautifully reimagined three-bedroom, two-bath home pairs relaxed coastal style with breathtaking views of Tampa Bay and unforgettable outdoor living.

Start your mornings with coffee as boats drift by, spend your afternoons lounging poolside in the sunshine, and end the day watching the sky turn shades of pink and gold over the water.

The outdoor living space is truly the star of the show. A spacious covered gazebo creates a breezy waterfront lounge where you can relax in the shade, dine alfresco, or gather with friends and family while enjoying uninterrupted views across the bay. Just steps away, the sparkling waterfront pool offers the perfect place to cool off while taking in the peaceful beauty of Tampa Bay. Lounge by the water under shaded umbrellas, or gather around the firepit in the evening as the sky turns shades of pink and gold over the bay.

Inside, the home has been completely transformed with a thoughtful designer remodel that blends bright coastal style with warm natural textures and elegant finishes. The open living and dining areas feel light and inviting, creating a perfect space for gathering after a day of exploring the island.

Each bedroom reflects the calm coastal palette found throughout the home, creating a relaxed atmosphere that perfectly matches the waterfront setting.The main living level features a spacious king bedroom and full bathroom, offering a comfortable retreat just steps from the heart of the home. On the ground floor, two private queen bedrooms share a Jack-and-Jill bathroom. These rooms can be accessed either through the ground-level entrance or via a spiral staircase inside the home.

Located on the quiet and highly sought-after North End of Anna Maria Island, The Lookout places you just moments from Bean Point, Pine Avenue’s shops and restaurants, and some of the island’s most beautiful beaches. Whether you spend your days biking the island, exploring nearby beaches, or simply relaxing by the water, this home offers an unforgettable Anna Maria Island experience.

With its incredible bayfront setting, stunning outdoor living spaces, and beautiful designer interiors, The Lookout is the kind of island retreat guests remember long after the vacation ends.

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 3 vehicles in the driveway only. No parking 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.