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.

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. Relax and take in the stunning sunsets from your own luxury beachfront home on Anna Maria Island, creating unforgettable memories in your home away from home.

Be sure to browse our listing of luxury vacation rentals by bedroom: 2 Bedrooms, 3 Bedrooms, 4 Bedrooms, and 5+ Bedrooms.

Properties Available 5 properties available
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.A luxurious 2,825 sq. ft. canal-front home featuring a heated pool, spa, and spacious living areas designed for relaxation and comfort.HIGHLIGHTS: Open Concept Living:&nbs
Hot HOT 60
Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$540.00 - $1,950.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
Welcome to A Shore Thing!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 the ultimate island getaway in this waterfront luxury retreat, perfectly situated just moments from the powdery white sands of Anna Maria Island and the charming boutiqu
Hot HOT 44
A Shore Thing
A Shore Thing
Anna Maria
$580.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 10 guests
Rating 5 (8)
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.Newly Built Luxury Canal-Front Home with Pool, Spa, and Private DockHIGHLIGHTS: Private Single-Family Home: Unique and spacious layout, professionally designed for comfort and luxu
Hot HOT 44
Tern Key
Tern Key
Anna Maria
$900.00 - $2,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
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 unparalleled luxury at AcquaLuxe, a stunning canal-front retreat on Anna Maria Island featuring a heated pool, private dock, gourmet kitchen, and upscale amenities designed
Hot HOT 69
AcquaLuxe
AcquaLuxe
Anna Maria
$750.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (6)
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.Discover the ultimate in coastal luxury at Bateman's, a stunning canal-front retreat perfect for families and friends seeking an unforgettable Anna Maria Island getaway.2543 sq
Hot HOT 40
Bateman's
Bateman's
Anna Maria
$560.00 - $2,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (11)

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