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

Villa #7 AMI Lime Fish by AMI Locals 3602 Gulf Dr, Unit #1, Holmes Beach, FL 34217 Welcome to Villa #7 AMI Lime Fish, a beautifully designed two-bedroom, two-bath beach villa located at the Islands West Resort! Just a two-minute walk to the white sandy beaches of Holmes Beach, this villa combines coastal charm with resort-style amenities including

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Villa #7 AMI Lime Fish

Coconut Cove by AMI Locals 205 17th St N, Bradenton Beach, Florida TPL22-000085 Welcome to Coconut Cove by AMI Locals, a vibrant six bedroom, four and a half bath luxury beach home just a three-minute walk from the soft sands of Bradenton Beach. Perfectly designed for families and groups, this retreat combines island style, modern comfort, and endl

Coral Palms by Anna Maria Island Accommodations 209 81st St, Holmes Beach, FL 34217VRC16-000157Welcome to Coral Palms, a beautiful ground-level vacation home featuring three bedrooms and 2 bathrooms, perfect for families or groups seeking a relaxing escape on Anna Maria Island! Just a four-minute walk to the sparkling beaches of Holmes Beach, this

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Blissful Bay at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #4, Anna Maria, FL 34216 VR18-000088 Welcome to Blissful Bay at Bayside Bungalow, a bright and beachy three bedroom, two bath condo perfectly located on the north end of Anna Maria Island! Just across the street from the Tampa Bay and near the islands pristine white-sand beaches, t

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Blissful Bay at Bayside Bungalow

Sail Away by AMI Locals 241 Willow Avenue, Anna Maria, Florida 34216 VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front luxury home in the heart of Anna Maria Island. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is des

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Surf View by AMI Locals 209 54th St, Holmes Beach, FL 34217VRC18-000095Welcome to Surf View, an expansive eight bedroom, six bath luxury vacation home in Holmes Beach, perfect for large family gatherings, reunions, and group getaways. With a rooftop deck offering sweeping Gulf and Bay views, a resort style pool with waterslide and spa, and plenty o

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Sea Swept by Exclusive Vacations 2516 Gulf Dr N, Bradenton Beach, FL 34217 TPL22-000035 Welcome to Sea Swept, part of our Exclusive Collection. This beachfront luxury home boasts ten-bedrooms, eight-and-a-half-baths with breathtaking Gulf views, private beach access, and resort-style amenities. Located just steps from the pristine beaches, this h

EXCLUSIVE COLLECTION

Ocean's 77 by Anna Maria Island Accommodations 205 77th Street, Unit B, Holmes Beach, FL 34217VRC19-000012Welcome to Ocean's 77, a charming beach cottage just five houses from the stunning white sandy beaches of Anna Maria Island’s Holmes Beach! This two-bedroom, two-bath home offers a tropical backyard oasis with a private sparkling pool, a game r

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Three Little Birds Cottage by Anna Maria Island Accommodations 308 56th St, Unit B, Holmes Beach, FL 34217 Welcome to Three Little Birds Cottage by Anna Maria Island Accommodations, a stylish two bedroom, two and a half bath modern retreat with a bonus loft, located just a five-minute walk from the pristine sands of Holmes Beach. Perfect for famili

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Three Little Birds Cottage

Flip Flops and Fish Tales by AMI Locals426 Magnolia Ave, Anna Maria, FL 34216VR19-000035(Sat–Sat, 7-night minimum stay may be required during high season weeks)Home Under New Ownership • Recently Refreshed Interior and ExteriorWelcome to Flip Flops and Fish Tales, a beautifully updated three bedroom, two and a half bathroom coastal retreat located

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Flip Flops and Fish Tales

Periwinkle Place by Exclusive Vacations 226 Periwinkle Plaza, Anna Maria, FL 34216 VR25-000004 Indulge in the ultimate luxury beach home at Periwinkle Place, part of our Exclusive Collection. This stunning estate in the heart of Anna Maria offers six spacious bedrooms and six and a half bathrooms. Just a five-minute walk from the pristine shoreline

EXCLUSIVE COLLECTION

Coming in Hot by AMI Locals Anna Maria Island Luxury Home with Rooftop Deck and Pool VRC22-000171 Live the island dream at Coming in Hot, a stunning newly built four-bedroom, four-and-a-half-bath retreat located in Holmes Beach—just one minute from the sugar-white sands of Anna Maria Island. With a rooftop deck offering panoramic Gulf views, a res

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