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Escape to paradise in this newly remodeled 4-bedroom, 4-bathroom Anna Maria Island vacation rental on North Shore Drive. Enjoy your own private heated pool, plus a golf cart, bikes, paddle boards, and kayak for endless fun. This luxury coastal beach house is steps from the Gulf, perfect for families and...
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Escape to Salt + Sol, a stunning 4-bedroom canal-front home on Anna Maria Island. This bright and airy retreat offers a perfect blend of coastal elegance and modern comfort. Enjoy easy access to sugar-white beaches, charming boutiques, and delicious dining options. Relax in the sun-filled great room with...
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Escape to Shangri-La, a stunning beachfront estate on Anna Maria Island's coveted Bean Point. This private, gated sanctuary offers unparalleled Gulf views and direct beach access. Enjoy luxurious amenities, spacious rooms, and a serene atmosphere perfect for a memorable vacation. Experience the best...
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Escape to Beach Bliss, a stunning 4-bedroom, 3-bath waterfront home on Anna Maria Island. Enjoy the perfect blend of luxury and relaxation with a private pool and spa, ideal for soaking up the Florida sun. With beach access and water activities nearby, your dream island getaway awaits.The Space Backyard...
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Experience the ultimate Anna Maria Island getaway at Tripletail! This stunning 4-bedroom, 4-bath bayfront home offers breathtaking waterfront views and is perfectly located near Pine Avenue and the City Pier. Enjoy mornings watching dolphins, afternoons by the private pool, and evenings relaxing in the...
Featured review
Beautiful, outstanding home with unbelievable views from every window! The water is right outside your door. Plus there's a hot tub out back and a pool out front. It was a very memorable trip that I'll...
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Escape to Fanta-Sea, your private tropical retreat on the coveted north end of Anna Maria Island — where backyard fun, beachside relaxation, and effortless island exploring come together.Step through your back gate and feel the soft Gulf sand beneath your feet. This ground-floor coastal haven...
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Wake up to the sound of waves and step straight onto the sugar-white sands of Anna Maria Island. Serendipity Gulf is your private beachfront sanctuary on the coveted north end—where relaxed bohemian style meets unforgettable Gulf views.Just completed: a stunning beachside heated pool, perfectly...
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Escape to Beach Escape, a charming 3-bedroom, 3-bathroom Mediterranean-style house in the heart of Holmes Beach, Florida. Enjoy easy access to the pristine beach, walkable dining and shopping, and a free trolley stop. This home offers a private outdoor oasis with a heated pool, outdoor dining, and a gas...
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PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered during that time and are reflected in the pricing.This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!Cottage 110A is a beautifully...
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Escape to Sandcastle, a stunning Anna Maria Island house with breathtaking beach and water views! This family-friendly retreat boasts a private pool, is steps from the beach, and offers luxurious amenities like a complimentary 6-passenger Golf Cart, BBQ grill, and bikes. Enjoy the perfect blend of relaxation...
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Escape to Serendipity, a luxurious beachfront haven on Anna Maria Island! This stunning 4-bedroom home offers direct beach access, a beachfront hot tub, and an elevator for easy access. Enjoy breathtaking sunsets, king beds in every room, and a 6-passenger golf cart. With bikes, paddleboards, and kayaks...
Distance to beach: 50 feet to across the street
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Key Lime Cottage is a charming 3BR/2BA coastal retreat just across the street from the Gulf beach and two houses from the iconic Rod & Reel Pier. This pet-friendly home features a private fenced yard, hot tub, bikes, and paddle boards, plus a fully stocked kitchen, Smart TVs, and fast Wi-Fi. Walk...
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Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group needs for an unforgettable island escape — from elegant interiors...
Featured review
This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!
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Wake to waves and end each day with award-winning Gulf sunsets at Limefish Luxe—a Gulf-front, 3BR/3BA luxury retreat in North Holmes Beach. Enjoy direct beach access, a private heated pool, complimentary 6-passenger golf cart, bikes, paddle boards, and beach gear. Steps from the best of Anna Maria...
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Escape to Serendipity Deux, a luxurious 4-bedroom house on Anna Maria Island, where refined interiors meet the laid-back island lifestyle. Enjoy premium beach access and a prime location near Bean Point and Rod & Reel Pier. This stunning retreat offers the perfect blend of comfort, privacy, and coastal...
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Escape to Waves, a stunning house on Anna Maria Island, offering luxurious comfort and direct beach access. Perfectly positioned just across the street from the beach, Waves offers stunning water views and the convenience of stepping from your front door to the sugar-white sands in moments.The Space The...
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Discover The Salty Fern, a stunning 3-bedroom, 2-bathroom house on Anna Maria Island's desirable North End. This stylish coastal retreat boasts a private pool, ideal for relaxing after a day at the beach. Enjoy easy access to pristine beaches, water activities, and the charm of Anna Maria.The...
