Featured Properties
Our Anna Maria Vacations Featured Properties still have select Availability! Book an unforgettable vacation today and experience all the beauty of Anna Maria Island and the surrounding area. These rental homes offer incredible pools, beautiful interiors, and a wonderful space to relax and enjoy a little “Island Time”. Our expert Reservations team is ready to answer any questions, so please feel free to call us at 941-778-4178.
14 properties available
Direct Beach Front by Anna Maria VacationsCondo in Bradenton Beach, FL TPL18-000062 / CND5105467Welcome to Direct Beach Front by Anna Maria Vacations, a beautiful Gulf-front condo offering panoramic views of the turquoise waters from nearly every room. Located on the second level of the Sandcastle Condominium, this three-bedroom, two-bath retreat f
Villa Sand Dollar by Anna Maria VacationsWelcome to Villa Sand Dollar, a charming three-bedroom, two and a half bath Holmes Beach vacation rental just a 2-minute walk to the sugar white sands of Holmes Beach on Anna Maria Island This inviting coastal townhouse retreat offers a private pool, spacious outdoor living, and easy access to the Holmes Bea
Bright, breezy, and effortlessly warm – welcome to The Salty Perch – thoughtfully outfitted to be the backdrop to your favorite vacation memories. Designed for romantic escapes and small family getaways, this inviting one-bedroom, one-bath condo features a king bed in the primary suite and memory foam queen sleeper in the living room. Located steps
Ocean Breeze by Anna Maria Vacations Duplex in Holmes Beach, Florida VPR16-000337 Discover Ocean Breeze, a perfect Gulf Coast escape in the heart of Anna Maria Island! Offering four spacious bedrooms and three bathrooms, with a spectacular backyard featuring a private pool, in-ground spa, and a covered patio with outdoor seating and a BBQ grill.
Buttonwood Cottage by AMI Locals Welcome to Buttonwood Cottage, a recently restored three bedroom, two bathrooms home full of Florida charm. Perfectly located on iconic Pine Avenue in Anna Maria and 10-minute walk to the Gulf. With a private heated pool, a pet-friendly policy, and easy access to island boutiques, restaurants, and attractions, this
Island Bay House Unit A by Anna Maria VacationsWelcome to Island Bay House Unit A, a three-bedroom, two-bath waterfront duplex vacation rental in Holmes Beach. Located on the third floor of a unique two-unit property, this private rental offers beautiful waterfront surroundings, a shared enclosed indoor pool, and an approximately seven-minute walk
Island Bay House Unit B by Anna Maria VacationsWelcome to Island Bay House Unit B, a three-bedroom, two-bath waterfront vacation rental in Holmes Beach. Located on the second floor of a unique two unit property, this private rental features a shared enclosed indoor pool and an approximately seven-minute walk to Manatee Public Beach. Its king, queen
Peachy Keen by AMI Locals VPR22-000026 Escape to Peachy Keen, a luxurious family vacation rental on Anna Maria Island! This spacious three-bedroom, plus loft, home is just 200 steps from the Gulf, offering stunning water views and easy access to the island’s best amenities. Wake up to breathtaking sunsets, splash in your private saltwater pool, or
Sugar Beach by Anna Maria Vacations Duplex in Holmes Beach, FloridaVRC16-000340 Make your vacation dreams come true at Sugar Beach, a charming island retreat just minutes from Holmes Beach’s white sandy beaches! This spacious three-bedroom, two and a half bath home features a private backyard with a sparkling pool, covered patio with outdoor dini
Gypsy Sol by Anna Maria Island Accommodations VR18-000034 Welcome to Gypsy Sol, your ultimate Anna Maria Island escape! This four bedroom, two bath canal front vacation home is packed with fun and relaxation, featuring a private pool, hot tub, and ping pong table for endless entertainment. Just a short stroll from Pine Avenue’s charming boutiques,
Island Tropical Villa by Anna Maria Vacations Condo in Holmes Beach, Florida VRC19-000249Welcome to Island Tropical Villa, a charming three-bedroom, two-bath vacation home located just a five-minute walk from the turquoise waters and white sand of Holmes Beach. Perfect for families and small groups, this newly updated retreat offers multiple outdoo
Sunny Side Down by Anna Maria Vacations Duplex in Bradenton Beach, Florida VRC16-000153 / DWE5105831Welcome to Sunny Side Down, a colorful and cozy duplex perfect for families or small groups seeking a tranquil beach escape! Located just three minutes from the white sandy beaches and a short trolley ride to Bradenton Beach shops, restaurants, and
