Holmes Beach Vacation Homes for Sale

Coastal Elegance Meets Modern Luxury Just Minutes from the Gulf. Discover the ultimate island living with this newer custom-built luxury beach home, just moments from the pristine shores of the Gulf. Designed for both style and functionality, this home features 4 spacious bedrooms, 4.5 bathrooms, plus a private study and inviting den, offering flexible spaces for work, relaxation, or entertaining.

Unique opportunity to own one of the most prestigious waterfront lots on Anna Maria Island. The lot is 23,634sqft and features over 300 feet on open water with a 180 degree view of Watsons Bayou, Intracoastal Waterway and Anna Maria Sound. The lot is perfectly situated in a protected no wake zone with deep water access. It is also conveniently a 1 min drive straight to the beach.

Discover the Coastal Chic Beach House, a stunning residence featuring four bedrooms and 3.5 baths, which has undergone an impressive transformation by renowned interior designer Adrian Griffin.

Ask about our rent to own option! This newly renovated waterfront home on Anna Maria Island features nearly 80 feet of prime canal frontage, providing breathtaking views from almost every room of the property. A private boat dock and lift make this residence a paradise for boating enthusiasts, while also being only steps away from the beach.

Under contract-accepting backup offers. Located adjacent to the sparkling gulf waters this inviting triplex is a great investment opportunity for those seeking both charm and versatility, offering a diverse array of units: a 3BD/2BA, a 2BD/2BA, and a 2BD/1BA, each offering unique and comfortable living spaces.

Under Construction. Under Construction by Award-Winning Builder Stunning 4 bedroom, 3.5 bath modern coastal contemporary home by Modus Builders — recipient of the 2025 Home of the Year honors earlier this year — located at 2908 Avenue B on Holmes Beach, with an estimated completion of May 2026.

Exceptional Gulf-Front Opportunity in the Heart of Holmes Beach! Discover the perfect blend of island charm and coastal luxury with this rare gulf-front parcel on Anna Maria Island. Ideally located just steps from the sugar-white sands, and surrounded by the vibrant energy of Holmes Beach’s shops, restaurants, and island attractions, this property offers unlimited potential.

Storm-ready luxury meets waterfront serenity — live confidently on Anna Maria Island!!! Welcome to 634 Key Royale Drive—an elevated, energy-efficient canal-front home offering peace of mind just minutes from the sugar-sand beaches of Anna Maria Island. Built in 2011 by Shoreline Builders, this 4 BD / 3.

Paradise is Here! 6-Bedroom, 5-Bathroom Furnished, Turnkey Island Retreat in Holmes Beach Welcome to your dream beachside escape: This stunning 3-level single-family home is located just one block from the powdery sand beaches of the Gulf coast in highly sought-after Holmes Beach on Anna Maria Island.

It's time to make Anna Maria Island your home. Discover a rare opportunity to own an iconic piece of Holmes Beach history. Designed by Emily-Anne Smith, this beloved island residence is known for its signature pink exterior and timeless coastal charm.

Experience understated elegance in this contemporary coastal 5BR/4BA home located in the esteemed Key Royale community on Anna Maria Island. Thoughtfully designed and impeccably finished, this residence exudes quiet luxury from the moment you step inside. Soft natural light, refined materials, and serene water views create a sense of calm throughout the open concept living spaces.

Luxury Beach Retreat Just 2 Minutes from the Gulf! Welcome to Beach Breeze, a coastal oasis designed for pure relaxation and unforgettable memories. This beautifully appointed 6-bed, 4.5-bath home blends high-end luxury with the easy comfort of beachside living—perfect as a personal getaway or a standout vacation rental.