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.

224 properties available

Covey Cottage by Anna Maria Island Accommodations 418 Spring Ave, Anna Maria, FL 34216 VR16-000292 Welcome to Covey Cottage by Anna Maria Island Accommodations, a three bedroom, three and a half bathroom vacation home with a private pool and an unbeatable location. Just a seven-minute walk to the white-sand Gulf beaches and one minute to Pine Avenu

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The Curated Palm by Anna Maria Island Accommodations 520 Kumquat Drive, Anna Maria, FL 34216 Welcome to The Curated Palm, a four bedroom, four and a half bath luxury canal-front home designed for multi-family vacations, group getaways, and extended stays. This stunning retreat offers resort-style outdoor living with a private saltwater pool, oversi

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Stones Throw by Anna Maria Island Accommodations Holmes Beach Beachside Getaway with Pool VRC16-000152Welcome to Stones Throw, a charming two-bedroom, one-bath vacation home in the heart of Holmes Beach! Just a four-minute walk to Holmes Beach, this bright and airy retreat features access to a community shared heated pool, a screened-in lanai, pet-

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Hip Nautic by AMI Locals 870 N Shore Dr, Anna Maria, Florida 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 pr

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Turtle Crawl by Anna Maria Island Accommodations 763 Jacaranda Rd, Unit B, Anna Maria, FL 34216VR16-000350Welcome to Turtle Trax, a cozy ground-level duplex tucked away in the peaceful north end of Anna Maria Island. Just a five-minute walk to the beach, this two-bedroom, two-bath vacation rental offers a shared backyard pool surrounded by lush lan

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Pineapple Palms by Anna Maria Island Accommodations 308 64th St, Holmes Beach, FL 34217VRC17-000041Welcome to Pineapple Palms, the ultimate ocean-loving getaway just two-and-a-half blocks from the stunning beaches of Holmes Beach! Perfect for a small family or friends, this charming two-bedroom, two-bathroom home offers a private heated pool, lush,

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Ohana by Anna Maria Island Accommodations 4807 2nd Ave, Holmes Beach, FL 34217Experience the perfect family vacation at Ohana, a stunning four-bedroom, three and a half bath home just a three-minute walk from the white sands and turquoise waters of Holmes Beach! This beautifully furnished home features a private pool shaded by graceful palms, an o

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Honey I'm Holmes by Anna Maria Island Accommodations305 73rd St Holmes Beach, FloridaWelcome to Honey I’m Holmes! Start your island getaway here at our newly refreshed coastal home in a charming neighborhood of Holmes Beach! This gorgeous, modern four bedroom, three bath retreat is a short walk to the glistening sandy beaches of the Gulf! An open l

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Two Pina Coladas by Anna Maria Island Accommodations 123 46th St, Holmes Beach, FL 34217 VRC16-000094 Welcome to Two Pina Coladas by Anna Maria Island Accommodations, a luxurious six bedroom, four and a half bath home just one block from the Gulf beaches of Holmes Beach. Designed for large families and groups, this coastal gem combines resort style

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Tide of Your Life by AMI Locals 106 12th St S, Bradenton Beach, FL 34217 TPL22-000073 Welcome to Tide of Your Life, a spectacular nine bedroom, nine and a half bath luxury retreat in Bradenton Beach. Just a one-minute walk to the beach, this home features a rooftop deck with beach views, a private pool with spa and sun shelf, and spacious indoor an

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The Royal by Exclusive Vacations 3015 Avenue E, Holmes Beach, FL 34217 VRC23-000111 Experience luxury and island paradise at The Royal, part of our Exclusive Collection. This designer four-bedroom, five-and-a-half-bath beachfront home is just steps from the soft powder sands of Anna Maria Island! This three-level estate boasts a spectacular roofto

EXCLUSIVE COLLECTION

Queen Palm by Anna Maria Island Accommodations 5701 Holmes Blvd, Unit B (North), Holmes Beach, FL 34217 VRC19-000042 Welcome to Queen Palm by Anna Maria Island Accommodations, a cozy two-bedroom, one-bath ground-level retreat located less than a five-minute walk from the white-sand shores of Holmes Beach. Perfect for couples, small families, or fri

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