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.
19 properties available
Dolphin House by Anna Maria Vacations Duplex in Holmes Beach, FloridaVRC16-000338Experience the tropical charm and luxury of Dolphin House, a beautiful three-bedroom, two-and-a-half-bath townhome just a six-minute walk from the beach in Holmes Beach! This stunning home features a brand-new sparkling pool with a gorgeous waterfall, a covered patio w
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
Beach Escape by AMI Locals Vacation Rental License #VR18-000090 Welcome to Beach Escape, a stunning five-bedroom, four-bath luxury home just one street from the powdery white sands of Anna Maria Island. Ideally located on the peaceful north end near Bean Point Beach, this coastal retreat combines upscale comfort with endless outdoor fun. Spend your
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
Starfish Cove, B by AMI Locals Duplex in Holmes Beach, FLVRC21-000189Welcome to Starfish Cove, B, a charming beach-themed retreat in Holmes Beach! This two-bedroom, one-bath vacation home is ideal for small families seeking a cozy, functional escape just minutes from the shoreline. Located on Palm Drive, this home offers easy access to the Anna Mar
Hawaiian Hideaway by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000298 Welcome to Hawaiian Hideaway, a tropical duplex paradise just a short 5-minute walk from Holmes Beach! This spacious four-bedroom, two-bath home offers a serene backyard retreat featuring a private pool with a built in table, ample outdoor seating, and a BBQ gr
Hip Nautic by AMI Locals Vacation Rental License #VR22-000090 Welcome to Hip Nautic, a luxury four bedroom, four and a half bath beach retreat just steps from the beautiful bayside shores of Anna Maria Island. Perfectly situated near Pine Avenue’s shopping and dining, this modern, pet-friendly home offers upscale amenities including a private pool
Changes in Latitude #403 by AMI Locals Vacation Rental License #STR23-00171Welcome to Changes in Latitude #403! This gorgeous penthouse condo offers three bedrooms and three full bathrooms in a newly built luxury community overlooking Anna Maria Sound! With sweeping water views from the oversized screened-in lanai, custom interior finishes, and res
Shells and Sunshine by Anna Maria VacationsHome in Anna Maria, FL VR16-000437Discover Shells and Sunshine, a family-friendly beach-front retreat on the prestigious north end of Anna Maria Island! This charming home features two levels with three bedrooms and two bathrooms, accommodating up to eight guests. Enjoy unobstructed views of the ocean from
Whim Sea by AMI Locals Vacation Rental License #STR23-00173 Welcome to Whim Sea, your luxurious top floor penthouse escape in the exclusive gated community of One Particular Harbor at Margaritaville! This stunning residence features two spacious primary suites, two bathrooms, and panoramic sunrise views over the marina and mangroves. A short drive
Villa Portofino by Anna Maria Vacations VRC18-000050Experience the perfect family vacation at Villa Portofino, a charming island retreat just a short walk from the pristine beaches of Holmes Beach! Offering five bedrooms, three and a half bathrooms, and a private backyard oasis featuring a sparkling pool, lush tropical landscaping, and outdoor livi
Sea Place by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000265 Welcome to Sea Place, a beautiful island bungalow with a private heated pool, tropical style, and all the comforts of home. Just a short 3-minute walk from the beach, this three-bedroom, two-bathroom ground level retreat is perfect for families or small groups seeking a
