Anna Maria Single Family Homes For Sale - 83 homes

Remarks: Come take a look at this amazing Anna Maria home ready for you and your family to come live in paradise. Villa Maria is ready for you! An amazing 3 bedroom, 2 bathroom and a half bath just 2.5 blocks away from some of the most coveted beaches in the country. This popular vacation rental is perfectly nestled in the city of Anna Maria. Walking distance, a bike ride or short golf cart ride to the beautiful beaches of the Gulf of Mexico where you can bask in the sunshine all day. Or take in one of the most amazing sunsets in the world. Villa Maria is also close to all the happenings on Pine Avenue. Take in the shopping and grab a bite at one of the delicious restaurants. Villa Maria has been beautifully remodeled with the upmost attention to detail and beauty. As soon as the home comes into view, you will feel its character and beach vibe. Walk through the carport, just past the outdoor ping pong table and you'll enter the home. With a clean bright fully equipped kitchen, a dining table that seats 6, and a cozy living room ready for family night. Along with an additional family so the kids can have all the space they need for fun. The beautiful primary bedroom and bathroom are up stairs and away from the all the action. You will feel as if you entered a spa and be able to escape and chill out whenever you need. The other two bedrooms are beautifully decorated and ready for the rest of the family and or friends. Enjoy dining in the sun soaked dining area inside or you can take the fresh catch outside to the outdoor dining area just off the incredible pool. With lush landscaping and the feel of privacy, you'll want to spend the day by the pool. Villa Maria is a very popular vacation rental and could be your ticket to Anna Maria Life. It’s beautiful, full of fun and close to it all.

Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)

Listing Agent: Billi Gartman (941-545-8877)

Remarks: ***Welcome to Summer Breeze — a rare island gem on Anna Maria Island’s coveted North End.*** This elevated 5-bedroom, 4-bath "Old Florida Coastal Retreat" sits on an oversized corner ¼-acre lot surrounded by lush tropical landscaping, just steps from the world-famous Bean Point beaches. Whether you’re seeking a family getaway or a compelling short-term rental opportunity, this home delivers. The flexible floor plan includes multiple suites and bunk rooms, offering exceptional sleeping capacity. The open-concept main living area features a coastal-inspired kitchen with granite countertops, ample storage, and seamless indoor-outdoor flow to a large screened balcony. Grandfathered to accommodate up to 14 guests, this is a rare and valuable rental advantage on the North End. Outdoors, enjoy a private Tropical Oasis with a heated pool and spa, fenced yard, covered entertainment area, and two driveways with ample parking — an increasingly rare island feature. Elevated construction offers covered parking and elevated systems for added peace of mind. Offered fully furnished and turn-key, the home includes hurricane-impact windows and doors, newer metal roof, updated plumbing and electrical, new water heaters, elevated AC units, and all-new pool equipment. Investor Opportunity - Current rental performance reflects conservative management, presenting a strong value-add opportunity & appreciation. Comparable 5-bedroom homes within walking distance to the beach consistently outperform under optimized short-term rental strategies. Offered at $880 per square foot, this property represents one of the BEST VALUE propositions for a large-occupancy vacation rental on Anna Maria Island. Just a short two block stroll to Bean Point, and walking distance to Pine Avenue, and local favorites, Summer Breeze offers laid-back island living with serious investment upside. Seize this opportunity in 2026 to own your FLORIDA PARADISE!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)

Listing Agent: Stacy Cunneen (941-730-6194)

Remarks: Let the island breeze guide you home to 505 S Bay Boulevard, a waterfront haven where the world slows down and coastal living feels like poetry. Tucked along the tranquil north end of Anna Maria Island, this elevated five-bedroom, five-bath home invites you to experience a lifestyle wrapped in beauty, comfort, and pure island magic. Step inside and discover more than 3,200 square feet of thoughtfully designed living space, filled with natural light and framed by sweeping water views. The open-concept floor plan flows seamlessly, anchored by a gourmet kitchen featuring dual islands, high-end finishes, and a gas cooktop—perfect for everyday living and effortless entertaining. Multiple ensuite bedrooms, a versatile top-floor loft, and separate living areas provide privacy and flexibility for family, guests, or long-term stays. Four balconies extend the indoor spaces outdoors, offering uninterrupted views of sunrises over the bay and serene evenings on the water. This gorgeous home also presents a strong investment opportunity, with the potential to generate six-figure annual vacation rental income. Custom features abound, including a heated saltwater pool, a boat dock and lift on the canal, an eco-friendly rainwater cistern system, two tankless water heaters, an R38 metal roof with spray-foam insulated walls for energy efficiency, and a 25-year termite warranty for added protection. For boating enthusiasts, the home’s 32 feet of saltwater-canal frontage, deeded boat slip, and lift provide direct access to the Intracoastal Waterway and Gulf of Mexico. Durable coastal construction, impact-resistant features, and low-maintenance materials ensure peace of mind while embracing the waterfront lifestyle. Beyond the home, Anna Maria Island offers one of Florida’s most celebrated coastal experiences. A short stroll or bike ride takes you to Pine Avenue’s boutiques, cafés, and galleries, while world-renowned beaches with soft white sand and clear blue water await for sunbathing, shelling, or paddleboarding. From casual beach days to boating excursions and sunset views over the Gulf, this address delivers a truly effortless island lifestyle. At 505 S Bay Boulevard, you’re not just investing in a home—you’re securing a front-row seat to the island life that makes Anna Maria Island one of Florida’s top coastal destinations. Here, every day feels like a retreat, and every moment is framed by the natural beauty and charm of one of the Gulf Coast’s most desirable communities.

Listing is courtesy of: SIGNATURE REALTY ASSOCIATES (813-689-3115)

Listing Agent: Brenda Wade (813-655-5333)