Five+ Bedroom Vacation Rentals
Explore our curated collection of 5 bedroom homes on Anna Maria Island, thoughtfully designed for elevated group stays and refined coastal living. These spacious homes feature designer interiors, private amenities, and beautifully integrated indoor and outdoor spaces.
Whether you're planning a multi-family getaway or a special occasion, each home offers a high-end island experience with intentional detail and effortless comfort.
4 properties available
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 Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Where gathering comes naturally and every generation finds its place in the sun.Just steps from the Gulf of Mexico in Bradenton Beach, this dual-home property offers
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 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
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