Anna Maria Island Waterfront Vacation Rentals

View of the canal from one of our luxury waterfront vacation rentals. In the foreground is a private heated pool with a spacious deck and six lounge chairs. Beautiful tropical vegetation frames the photo.
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.

Experience the ultimate island escape with our Anna Maria Island waterfront vacation rentals, where breathtaking ocean views and the soothing sounds of waves greet you each morning. Whether you’re eager to explore the island’s pristine waters with kayaking, enjoy a day of fishing off the private dock, or simply unwind on the nearby white sandy beaches, we have the perfect rental to suit your needs. 

Looking for something specific? Explore our luxury vacation rentals by size — 2-, 3-, 4-, and 5+ bedroom homes.

Properties Available 4 properties available
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
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Bateman's
Bateman's
Anna Maria
$600.00 - $1,900.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (14)
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
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Tern Key
Tern Key
Anna Maria
$900.00 - $1,850.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (8)
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
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.AcquaLuxe
.AcquaLuxe
Anna Maria
$650.00 - $2,050.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (12)
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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Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$600.00 - $1,750.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (9)

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