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

Buttonwood Cottage by AMI Locals 405 Pine Ave, Anna Maria, Florida 34216 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 boutiq

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Margarita-Ville by Anna Maria Island Accommodations 121 46th Street, Holmes Beach, FL 34217VRC16-000136Experience the ultimate island escape at Margarita-Ville, a stunning six-bedroom, four and a half bath vacation home designed for large families or groups seeking a memorable getaway! Just a two-minute walk from the beach, this beautifully landsca

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Beachly Beloved by AMI Locals 2206 Avenue A, Bradenton Beach, FL 34217 Welcome to Beachly Beloved, a stunning 7-bedroom, 7.5-bathroom luxury beach home just a 5-minute walk from Bradenton Beach. Designed for large families and groups, this coastal chic retreat features a private pool and spa, a rooftop deck with sweeping Gulf and Bay views, and ele

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Another Paradise by Anna Maria Island Accommodations 115 Willow Ave, Anna Maria, FL 34216 VR16-000382 Welcome to Another Paradise, a beautifully designed three-bedroom, three-bath coastal retreat located just a two-minute walk from the white sands of Anna Maria Beach. Perfect for families or small groups, this Anna Maria Island accommodation offers

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Seaside Manor by Anna Maria Island Accommodations 106 8th St S, Bradenton Beach, FL 34217 Welcome to Seaside Manor, a beautifully updated 3-bedroom, 2-bathroom vacation home just a two-minute walk from the sugar-white sands of Bradenton Beach. With a private pool and spa, multiple living spaces, and a location steps from the free island trolley, th

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Mermaid’s Retreat by Anna Maria Island Accommodations 104 29th St Unit 3, Holmes Beach, FL 34217 Welcome to Mermaid’s Retreat, a bright and inviting two-bedroom, one-bath Holmes Beach vacation rental by Anna Maria Island Accommodations, perfectly positioned just steps from the sugar-white sands of the Gulf of Mexico. This charming upper-level cond

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La Mer by Anna Maria Island Accommodations 313 58th St, Unit A, Holmes Beach, FL 34217VRC18-000126Welcome to La Mer, a fabulous beach vacation home just a short stroll from the soft sandy beaches of Holmes Beach! This beautifully decorated, four-bedroom, three-bath estate offers a private pool with a built-in tiki bar, sun shelf, and hot tub. Just

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Mangoes on Magnolia by Anna Maria Island Accommodations 313 Magnolia Ave, Anna Maria, Florida Welcome to Mangoes on Magnolia, a three-bedroom, two-bath vacation home with a private pool and hot tub, located less than a 10-minute walk from the white-sand beaches of Anna Maria Island. Nestled in a quiet neighborhood just two blocks from Pine Avenue’s

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Gulf Horizons by AMI Locals 201 17th St N, Bradenton Beach, FL VPL22-000084Experience the ultimate Florida escape at Gulf Horizons, a spectacular three-level estate with seven bedrooms and six and a half bathrooms! Located just across the street from Bradenton Beach's pristine Gulf beaches, this home offers panoramic water views from the rooftop de

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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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Beach View Paradise by AMI Locals 2406 Avenue C, Bradenton Beach, Florida Experience the ultimate coastal elegance at Beach View Paradise, a brand new seven-bedroom, seven and a half bath luxury vacation rentals just steps from Bradenton Beach’s turquoise waters and powdery white sands. Perfect for large families or groups, thus stunning retreat fe

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Hammock Dreams by Anna Maria Island Accommodations 131 Hammock Rd, Anna Maria, FL 34216 VR16-000408 Welcome to Hammock Dreams! Escape to the peaceful island lifestyle at Hammock Dreams, a stunning canal-front home nestled in the heart of Anna Maria. With three bedrooms, two bathrooms, and a private pool, this tropical retreat is ideal for families

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