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

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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Just Breathe by Exclusive Vacations 415 N Bay Blvd, Anna Maria, FL 34216 VR23-000046 Welcome to Just Breathe, part of our Exclusive Collection. This luxury four bedroom, four and a half bath vacation home perfectly positioned on the Bayfront across from Tampa Bay and just a short walk to the Gulf beaches. This home pairs modern sophistication with

EXCLUSIVE COLLECTION

Called in Sic by Anna Maria Island Accommodations 813 Jacaranda Rd, Anna Maria, Florida 34216 VR18-000103 Welcome to Called in Sic, a stunning and newly renovated four bedroom, three bath luxury vacation home located just one block from Bean Point Beach access on the peaceful north end of Anna Maria Island! With a private heated pool and spa, rooft

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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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Shore Is Paradise by AMI Locals 315 N Bay Blvd, Anna Maria, Florida VR20-000087 Welcome to Shore Is Paradise, a modern four bedroom, four and a half bath home overlooking Bayfront Park on the north end of Anna Maria Island. Enjoy a private resort-style pool and spa, plus a rooftop deck with panoramic bay views and a putting green. You are a short

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Bo’s Beach Bungalow by Anna Maria Island Accommodations 306 N Shore Dr, Unit B, Anna Maria, FL 34216 Welcome to Bo’s Beach Bungalow, a two-bedroom, one-bath coastal villa in the heart of Anna Maria Island. This charming retreat is less than a five-minute walk from the soft white sands of Anna Maria City Beach and just a short stroll to Pine Avenue

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West Coast Best Coast by Exclusive Vacations 104 9th Street S, Bradenton Beach, FL 34217 TPL23-000099 Experience island luxury at West Coast Best Coast, part of our Exclusive Collection. This stunning seven-bedroom, seven and a half bath estate is just two houses from the beautiful Gulf on Anna Maria Island! Featuring a private pool with a sun she

EXCLUSIVE COLLECTION

West Coast Best Coast

Highlights• Newly Remodeled• Less than a 5-minute walk from the beach • Private Pool and Hot Tub• Putting Green, Corn Hole, and Ping Pong Table• Outdoor ShowerIsland Chic by Anna Maria Island Accommodations 212 67th St Holmes Beach, FL 34217Welcome to Island Chic, a beautifully renovated home featuring four bedrooms and four bathrooms. This incred

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Anna Maria Wave by Anna Maria Island Accommodations 2806 Avenue E, Holmes Beach, FL 34217 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 com

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The Sea Zoo by Anna Maria Island Accommodations402 Bay Dr. S, Bradenton Beach, FloridaWelcome to The Sea Zoo – Your Ideal Bayfront Escape! This gorgeous three-bedroom home is perfect for families and groups seeking a fun-filled getaway. Located just one block from Bridge Street and the Bradenton Historic Street Pier, you can easily explore the char

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Beach Haven by AMI Locals 5501 Holmes Blvd, Holmes Beach, Florida VRC18-000066 Welcome to Beach Haven, an eight bedroom, seven and a half bathroom luxury vacation home just a 5-minute stroll to the beautiful beaches of Anna Maria Island. This expansive, multi-level getaway is ideal for large family reunions or group vacations. With a private poo

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Gulf Shore Cottage by Anna Maria Island Accommodations9206 Gulf Drive, Anna Maria, Florida VR16-000101 Your dream beach vacation begins at Gulf Shore Cottage, a newly renovated four-bedroom, two-bathroom coastal retreat located just six houses from the pristine sands of the Gulf. With a private pool, foosball table, and pet-friendly policy, this ch

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