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.

266 properties available

Emerald Shores by Anna Maria Island Accommodations 214 Fir Ave Anna Maria, FloridaEmbark on your paradise getaway at Emerald Shores! This entire duplex features two vacation rental units, each boasting an identical floor plan with three bedrooms and two baths, totaling six bedrooms and four baths. Just steps from the beach, you and your loved ones

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Highlights• Less than a 5-minute walk to the beach• Private Pool• Putting Green• Near shops and restaurants• BBQ Grill and Outdoor SeatingSocial Nest by Anna Maria Island Accommodations 308 Pine AveAnna Maria, FL 34216Welcome to Social Nest, a second-level home above a business in the heart of Pine Avenue with a private backyard featuring a stunnin

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Villa #4 Sand Dollar by AMI Locals3605 Gulf Dr, Unit #4 Holmes Beach, FloridaWelcome to Villa #4 Sand Dollar, a charming one-bedroom, one-bath beach-style villa perfect for couples or solo travelers seeking a tranquil getaway. Nestled in the heart of Holmes Beach, Florida, this inviting property is just a two-minute walk from the sparkling Gulf of

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Seaside Serenity by Anna Maria Island Accommodations 301 Bay Dr N, Bradenton Beach, FL 34217 Welcome to Seaside Serenity, a charming two-bedroom, one-bath stilted villa perched directly on the serene waters of the bay. With panoramic sunrise views, a private dock, and an unbeatable location just a short 10-minute stroll from the white sand beaches

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Key Largo Cottage by Anna Maria Island Accommodations 315 62nd St Holmes Beach, FL 34217 Discover the ultimate family getaway at Key Largo Cottage, a charming bungalow-style vacation rental perfectly situated for your fun-filled escape to Anna Maria Island. This lovely home features three spacious bedrooms and three modern bathrooms, offering ever

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Sun Daze by Anna Maria Island Accommodations126 51st St, Unit B Holmes Beach, FL 34217VRC16-000103Discover the perfect beach getaway at Sun Daze, this 2-bedroom, 2-bathroom villa located on Anna Maria Island was recently remodeled in 2025. Only a few homes from beautiful Holmes Beach and a short stroll to “downtown” Holmes Beach, this updated prope

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Highlights • Less than a 5-minute walk to the beach • PoolAnna Maria Guest House 212 by Anna Maria Accommodations 212 Pine AveAnna Maria, FL 34216Welcome to Anna Marie Guest House 212, an inviting vacation rental one and a half blocks from the warm Gulf of Mexico waters and beach. This three-bedroom and two-bathroom getaway is above a small, local

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Anna Maria Guest House 212

Mangoes on Magnolia by Anna Maria Island Accommodations Anna Maria Vacation Home 313 Magnolia Ave, Anna Maria, FL Welcome to Mangoes on Magnolia, your ultimate island retreat nestled just two blocks from the charm and energy of Pine Avenue. This beautifully appointed three-bedroom, two-bathroom vacation home offers the perfect blend of privacy and

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Boundless Waves by Anna Maria Island Accommodations408 Magnolia Ave Anna Maria, FloridaWelcome to Boundless Waves, an incredible vacation home with six bedrooms and six-and-a-half bathrooms, where friends, family, and pets can relax and have endless fun. You'll be blown away by the resort-style pool and spa, perfect for hours of fun in the sun. Plu

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Sun Porch by AMI Locals 102 7th St S, Unit C, Bradenton Beach, Florida TPL21-000135 Welcome to Sun Porch, a vibrant 2-bedroom, 2-bathroom cottage located just one house away from the white sand shores of Bradenton Beach. Tucked into a friendly three-unit complex, this ground-floor retreat is ideal for couples or friends seeking a relaxed, walkable

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Gulf Pearl by AMI Locals Holmes Beach Luxury Beach Home with Pool & Spa VRC21-000130Welcome to Gulf Pearl, an exquisite four-bedroom, three-and-a-half-bath vacation home on Anna Maria Island! This coastal paradise boasts a sparkling pool, relaxing in-ground spa, and an inviting backyard oasis with a tiki umbrella, poolside bar, and outdoor TV,

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Coconut Lagoon by Anna Maria Island Accommodations Holmes Beach Exotic Retreat with Pool & Trolley Access VR16-000285Welcome to Coconut Lagoon, a stunning coastal escape just steps from the white sands of Anna Maria Beach! This spacious four-bedroom, three-bath home features a sparkling private pool, elegant outdoor living spaces, including a c

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