Holmes Beach Vacation Homes for Sale

Located in the quaint Shell Point condominium community, this second story end unit offers a rare 3BD/2BA layout filled with potential and ready for your personal touch. Featuring impact windows for peace of mind, this spacious condo invites natural light from multiple exposures, creating a bright and airy feel throughout.

ISLAND LIVING Meets INVESTMENT POTENTIAL– 2BR/2BA Condo in Holmes Beach! TURNKEY Airbnb/VRBO rental opportunity!!! Welcome to your slice of paradise on Anna Maria Island! This beautifully maintained 2-bedroom, 2-bathroom condo offers a bright, open living space designed for both comfort and income potential.

Watch dolphins play in Watson's Bayou. Soak up your spectacular bay views in a private setting with all the amenities - tennis/pickleball court, heated swimming pool, putting green, clubhouse, waterfront park, and shuffleboard.

Under contract-accepting backup offers. A rare find! - Lot is large enough to put in a pool! Rent analysis from island property manager came in at $45,000-$55,000 per year in gross rent. This will help you pay for your island getaway while you are away.

A rare opportunity to secure your piece of paradise in the highly sought-after Shell Point community on Watson's Bayou / Anna Maria Sound.

Turnkey Furnished 1-Bed, 1-Bath Condo Steps from the Beach on Anna Maria Island Enjoy island living in this elevated, turnkey 1-bedroom, 1-bath condo just steps from the public beach on Anna Maria Island.

Step into coastal living at its finest on Anna Maria Island! This beautifully furnished 2-bedroom, 2-bath condo offers a turnkey getaway just three blocks from the island’s iconic sugar-white shoreline.

Very nice 2 bedroom, 2 bath located in a very quiet and private area. This complex offers tennis, heated pool, coin laundry and covered parking. A very short walk to tennis courts, dog park, Duffy's Tavern and Hurricane Hanks. Easy to show and unit is unfurnished.

Prime Boat Slip in the Heart of Holmes Beach offering direct access to beautiful Tampa Bay this slip is the perfect launch point for boaters who value both convenience and prime location. Enjoy all the benefits of waterfront living without the waterfront price tag. The slip offers a 10,000 lb boat lift with water and fish cleaning station.

Now available for purchase, this 10x30 slip is currently configured as a jet ski slip and offers everything you need for easy access to Tampa Bay. Features include a 1,500lb jet ski lift with remote control, a dock box for storage, and convenient electric and water hookups. A davit post with an electric wrench makes it simple to move the jet ski onto land.

Beachside Luxury Rental – 3BR, 2.5BA with Pool Live just steps from the sand at 4808 Gulf Drive Unit B, an upscale and fully furnished 3-bedroom, 2.5-bath home located in the heart of Holmes Beach. Available for starting July 19th, this multi-level coastal retreat blends modern comfort with laid-back island living—perfect for a long vacation or seasonal stay.

Available for immediate move in. Leased Jan-Mar 2026. The rental rates are as follows: Off Season (May through December): $3,500 per week or $6,000 per month. In Season (January through April): $3,500 per week or $9,000 per month. The vacation home is beautifully renovated and elevated, with three bedrooms and two bathrooms. It features a large pool and spa in a tropical backyard oasis.