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Casa Cay by Duncan Real Estate

Welcome to Casa Cay! This Bay front pool home on Anna Maria Island sounds like an absolute paradise! With its prime location on the North end between the 2 piers, stunning views of the bay and the Sunshine Skyway, and direct access to a private bay beach, it offers the quintessential island experience. The layout of the house, featuring three bedrooms and three bathrooms, including two suites with ensuite bathrooms, sounds perfect for families or groups of friends looking for comfort and ...

Heated pool, 3-Story bay views, 5min walk to beach

Escape to The Blue Ark, a stunning architectural gem on Anna Maria Island, offering a serene retreat for families. This unique 3-story haven boasts breathtaking lagoon views, and as the island's only natural lagoon, you'll enjoy front-row seats to manatees and aquatic life. Enjoy fishing from the dock, relaxing in the private heated pool and spa, or take a short stroll to the Gulf. With an elevator, 3 bedrooms, 4.5 bathrooms, and extra spaces for kids, this home has everything families need.

Island in the Sun, luxury beach house,private pool

WELCOME to Island in the Sun ... this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay Beach offers narrow white sand beaches, views of the of the City Pier, the Skyway Bridge and the boats traveling back and forth in Anna ...

NEW Coastal luxury, so close to beach!

Modern & comfortable 2-bedroom, 2-bathroom stay is a short couple minute walk to the white sand beach of Anna Maria Island. The fully equipped kitchen has modern appliances, and the open layout provides plenty of space to relax. Step outside onto private outdoor space to enjoy a morning coffee, sit and relax, or watch the sunset! Newly outfitted for the 2025 season, with brand-new furnishings, linens, and everything you need for a comfortable stay. Side-by-Side Units – Book One or Both!

Charming cottage w/heated pool in prime location.

Welcome to an old Florida 'The Starfish Cottage" . Enjoy the private heated pool with lush tropical setting. Inside you'll find an open concept living space where dining area, kitchen and living room have been newly furnished with luxurious deep seat couches and lounge chairs, hardwood floors add to the charm. Fresh linens, bath and beach towels are provided along with basic toiletries. Decor has been collected over time and obtained from local artists for a unique old Florida style.

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Modern vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Bathroom with walk in shower * Small kitchenette with full-size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Off-street parking for one vehicle * Trolley stop across the street * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella, and cart * Steps to the beach!

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

Discount 33% June 3-Day and July 4-Day w/Dock-Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

Welcome to Heavenly Hideaway, a beautiful canal-front vacation home located just a few blocks from the beach. With 3 bedrooms and 3 bathrooms, this home is perfect for families and friends seeking an unforgettable getaway on Anna Maria Island. This retreat offers luxury and comfort, close to attractions, shops, and dining. Enjoy a serene outdoor oasis with a private heated pool, a private dock on a canal, and a fire pit for smores.