Anna Maria Island Waterfront Vacation Rentals
Real peace moves in waves. We curated these sanctuaries for the sunrise watcher, the quiet soul, and the water lover. Step onto your terrace and let the rhythm of the tide wash away the rest of the world.
Looking for something specific? Explore our luxury vacation rentals by size — 2-, 3-, 4-, and 5+ bedroom homes.
11 properties available
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceMornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each mom
Welcome to Ocean Sunrise!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation RentalsThe SpaceSet directly on the Bay in Bradenton Beach, Ocean Sunrise offers 4,793 square feet of bright, inviting living. The design balances elegance and ease—sun-filled rooms, expansive gathering spaces, and a backyard where the lin
Welcome to AcquaLuxe!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience AcquaLuxe — a canal-front home designed for inspiration, connection, and ease.The SpaceNestled near Anna Maria Island’s beloved north-end beaches and Pine Avenue
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi
Welcome to Happy Ours!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.JUST RELAUNCHED AS A RENTAL and UNDER NEW MANAGEMENT! Experience Happy Ours — a rare direct beachfront retreat tucked along Magnolia Avenue on Anna
Welcome to Bateman's!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Bateman’s — where thoughtful design and waterfront living come together.Set along a quiet canal on Anna Maria Island’s north end, this modern coastal h
Welcome to Cortez Dock & Dine!On Florida’s Gulf Coast (Cortez, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please note: Fresh, updated photos are on the way. The home has been thoughtfully refreshed following the hurricane, and while a few items may differ from previo
Welcome to Hangin’ on Hammock!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please Note: The pool and spa are currently under construction and are scheduled for completion by May 2026. Construction is set to begin January 1, 2026. Because the po
Welcome to The Curated Palm!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceThe Curated Palm is a home that feels at once elevated and effortless — where thoughtful craftsmanship, inspired design, and island living align in perfect h
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceSet between the Gulf of Mexico and the Intracoastal Waterway, Mariner’s Crossing offers balance — connection and privacy, activity and calm. With
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere connection meets calm, Sea La Vie Beach House brings family, friends, and loved ones together in a space designed for comfort, laughter, and easy island liv
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