Anna Maria City Vacation Rentals

Located on the North side of Anna Maria Island, Anna Maria City is the perfect destination for those seeking beautiful beaches and a family-friendly atmosphere. This charming "Old Florida" town offers beautiful sunsets and is surrounded on all sides by a beautiful white sand coastline and the tranquil turquoise waters of the Gulf of Mexico. Bean Point Beach and City Pier Park are two of the main beach attractions in this lovely and quaint city. With dolphins, manatees, and other marine life all around, Anna Maria City is a nature and beach lovers paradise. Local food and attractions offer something for everyone in your family, with plenty of activities to keep everyone entertained. Please browse our selection of finely appointed Anna Maria Island vacation rentals offering modern amenities and decorations. Anna Maria Island Accommodations offers the perfect vacation home rentals for your next getaway to Anna Maria City.

Frequently Asked Questions

What is Anna Maria Island known for?
Pristine beaches, crystal-clear waters, a laid-back atmosphere, historic landmarks, fresh seafood, and water activities like fishing, kayaking, and paddleboarding.

How far is Anna Maria Island from Miami?
Approximately 200 miles northwest, about a 3.5 to 4-hour drive.

How far is Anna Maria Island from Clearwater?
Approximately 40 miles south of Clearwater, about 1 to 1.5 hours by car.

225 properties available

Little Dream by Anna Maria Accommodations 203 64th St, Unit B, Holmes Beach, FL 34217VRC16-000139Welcome to Little Dream! A charming one-bedroom, one-bath getaway just steps from the stunning Anna Maria Beaches! Located in a vibrant gated community, this cozy home offers easy access to beautiful beaches, local shops, and all the local favorite rest

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Bay View Bliss by AMI Accommodations 117 7th St N Unit 29, Bradenton Beach, FL 34217 Welcome to Bay View Bliss, a newly remodeled two-bedroom, one bath coastal condo tucked in the heart of Bradenton Beach. Just a block from the beach, steps from the bay, and less than a mile from the vibrant Bridge Street district, this ground floor unit is your pe

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Two Sisters by Anna Maria Island Accommodations 6319 Gulf Dr, Holmes Beach, FL 34217 Escape to Two Sisters, an adorable three-bedroom, two-bath townhome nestled in a relaxed beach community of Holmes Beach! Just a five-minute walk to the soft sand and turquoise waters, this coastal retreat offers access to a community pool, a screened-in balcony,

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Lady From the Sea by Anna Maria Island Accommodations 205 Iris St, Anna Maria, FL 34216 VR18-000156 Welcome to Lady from the Sea, a coastal enchanted three bedroom, three and a half bathroom vacation home located on the coveted north end of Anna Maria Island! Just a six-minute stroll to the serene sands of Bean Point Beach and a short ride to Pin

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Emerald Shores East by Anna Maria Island Accommodations 214 Fir Ave, Unit B, Anna Maria, FL 34216 Welcome to Emerald Shores East, a three-bedroom, two-bath coastal duplex just one minute from the sugar white sands of Anna Maria Island. With beach views, a shared backyard pool, and a private deck for soaking in the Gulf breeze, this home combines co

Retreat Royale by Anna Maria Accommodations 604 Ambassador Ln, Holmes Beach, FL 34217 VRC19-000265 Welcome to Retreat Royale, a beautifully styled 2-bedroom, 2-bathroom island home nestled in a quiet neighborhood of Holmes Beach on Anna Maria Island! Designed for serenity and long-term stays, this charming retreat features a lush garden oasis, a sp

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Private Palms by Anna Maria Island Accommodations 132 48th St, Holmes Beach, Florida 34217 Welcome to Private Palms, a beautifully remodeled four-bedroom, two-bath coastal retreat just a 3-minute walk to Holmes Beach and close to the shops and dining of Holmes Beach Towne Center. This bright and stylish home features a private pool, relaxed outdoor

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Simply Chic by Anna Maria Island Accommodations 214 67th Street, Holmes Beach, FL 34217 VRC16-000105 Discover Simply Chic, a stylish four-bedroom, three-bathroom ground-level vacation home located just a three-minute walk from Holmes Beach. Designed for relaxation and fun, this coastal retreat features a private pool, putting green, and outdoor ga

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Bayfront Paradise by AMI Locals 238 S Harbor Dr, Holmes Beach, FL VRC18-000090 Welcome to Bayfront Paradise by AMI Locals, a spectacular 5-bedroom, 4.5-bathroom canal-front luxury home offering panoramic views of the Bay. Located in a quiet residential area of Holmes Beach, this coastal retreat combines elegance, relaxation, and adventure. With a p

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Bayfront Paradise (AMIL)

Bay View Beauty by Exclusive Vacations 881 N Shore Dr, Anna Maria, FL 34216 VR18-000097 Welcome to Bay View Beauty, part of our Exclusive Collection. This luxurious seven-bedroom, seven and a half bath beachfront home with direct beach access and unobstructed bay views. Ideally located along Anna Maria’s North Shore Drive, this luxury retreat place

EXCLUSIVE COLLECTION

Anna Maria Guest House 212 by Anna Maria Accommodations 212 Pine Ave, Anna Maria, FL 34216 Experience the relaxed charm of Anna Maria Island at Anna Maria Guest House 212. Located just one and a half blocks from the warm Gulf waters and beaches, this cozy and inviting three-bedroom, two-bath vacation home offers the perfect island escape. Situated

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Anna Maria Guest House 212

Island Breeze by Anna Maria Island Accommodations235 64th Street, Holmes Beach, FL 34217Experience the perfect beach retreat at Island Breeze, a stylish three-bedroom, two-bath townhome just a two-minute walk from Holmes Beach’s pristine Gulf beaches! Perfect for relaxation or adventure, this coastal gem offers a private screened-in porch, outdoor

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