Vacation Rentals
65 properties available
Crab Shack Anna Maria VacationsTownhome in Holmes Beach, Florida Welcome to Crab Shack, a charming two bedroom, two and a half bathroom Holmes Beach retreat just two blocks from the white sand shores of Manatee Beach. This cozy, modest island home offers a private heated pool, beach essentials, and easy walkability to the Holmes Beach Towne Center,
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
Away To Play by Anna Maria Vacations Home in Holmes Beach, Florida VRC20-000047 Welcome to Away To Play, a charming coastal retreat located just a few blocks away from the City of Anna Maria on Anna Maria Island! With just a 2-minute walk to the Beach, this beautifully designed four bedroom, two and a half bath vacation home features a private back
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
Ilha Bela by Anna Maria VacationsHome in Holmes Beach, Florida Welcome to Ilha Bela, a timeless three-bedroom, two and a half bath vacation home tucked away in the heart of Holmes Beach on beautiful Anna Maria Island. Blending classic Old Florida charm with modern comfort, this inviting getaway features a lush backyard oasis with tropical landscapi
Welcome to A Lil’ Nauti, a charming ground level home nestled in the heart of Anna Maria Island! This recently updated one-bedroom, one-bath retreat offers a cozy atmosphere combined with outdoor adventures just steps from the bay and a short, 4-minute bike ride to Holmes Beach. Perfect for couples or small families. Enjoy a peaceful seaside escape
Anna Maria Wave by Anna Maria Island Accommodations Welcome to Anna Maria Wave by Anna Maria Island Accommodations, a spectacular four-bedroom, four-bathroom beachfront home that captures the essence of coastal luxury on beautiful Anna Maria Island. Perfect for families and groups, this contemporary retreat combines modern design, breathtaking Gulf
Stay Calm by Anna Maria Vacations Home in Holmes Beach, Florida VPR16-000304 Welcome to Stay Calm, a beautiful ground-level vacation rental nestled just five minutes from Anna Maria Island’s white sandy beaches! This spacious three-bedroom, two-bath home offers a private sparkling pool, a screened-in lanai, and a covered patio perfect for family
Salty Margarita by AMI LocalsWelcome to Salty Margarita, a stunning three-level coastal retreat just two houses from the white-sand shores of Holmes Beach! This luxury Anna Maria Island vacation rental features four king suites, a private heated pool and spa, elevator access, and a rooftop deck with breathtaking Gulf and sunset views. With vibrant
Calypso Cottage by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000622Your island vacation starts at Calypso Cottage, a Mediterranean-inspired escape just a short stroll from Holmes Beach’s white sandy beaches on Anna Maria Island! This three-bedroom, three-bath home offers a private pool with a spa, a ping pong table, and tropical outd
Gulf Sands #102 by Anna Maria Vacations Condo in Holmes Beach, Florida VRC16-000363 Welcome to Gulf Sands #102, a charming 2-bedroom, 2-bath beachfront condo offering private Gulf access, sweeping coastal views, and an ideal location in the heart of Holmes Beach. Perfect for families and couples, guests will enjoy direct access to the white sand sh
