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

Banyan Manor by Anna Maria Island Accommodations 219 Chilson Ave Anna Maria, FL 34216VR20-000064Welcome to Banyan Manor! This stunning four-bedroom, four-bath canal-front vacation rental on Anna Maria Island is a dream retreat. Just a five-minute walk from the pristine Gulf of Mexico and within easy reach of the north end's popular restaurants and

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Highlights• 2-minute walk to the beach• Private pool, foosball table, and corn hole• Newly renovated• Across the street from Anna Maria Island trolley stop • Screened-in front porchGulf Shore Cottage by Anna Maria Island Accommodations 9206 Gulf Drive Anna Maria, FloridaVR16-000101Your dream beach vacation awaits at Gulf Shore Cottage! An original

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Love Me Blue by AMI Locals 792 Jacaranda Rd. Anna Maria, FL 34216Experience your vacation dreams at Love Me Blue! This stunning, brand-new luxury rental features 4 bedrooms and 4.5 bathrooms, making it the ideal choice for your family getaway on Anna Maria Island. A short walk leads you to the tranquil Bean Point beach, while just a mile away, you

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Seabreeze A by Anna Maria Island Accommodations Holmes Beach Family-Friendly Beach Retreat VRC16-000112Welcome to Seabreeze A, the perfect family-friendly condo just a three-minute walk from Manatee Beach in Holmes Beach! This cozy two-bedroom, two-bath home is ideal for creating lifelong memories with loved ones. Enjoy easy access to sandy beaches

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Bay Breezes at Bayside Bungalow by AMI Locals Bradenton Beach Bayside Retreat with Pool VR18-000088Welcome to Bay Breezes at Bayside Bungalow, a charming Anna Maria Island vacation rental offering two bedrooms, one bathroom, and a resort-style experience just steps from beautiful Bay beaches! This delightful coastal retreat features a lush shared h

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Bay Breezes at Bayside Bungalow

Highlights• Brand-New Construction• 2-minute walk to the beach• Private Pool and In-ground Spa• Rooftop Deck• Dog FriendlyLuna Sea by AMI Locals2109 Avenue C Bradenton Beach, Florida Welcome to Luna Sea, a brand-new home with high-end finishes and incredible amenities to create the finest vacation experience. This seven-bedroom and seven and a half

Highlights• Less than a 5-minute walk to the beach • Putting green• Private Pool• Ping pong table and Corn hole• Outdoor ShowerSimply Chic by Anna Maria Island Accommodations214 67th StHolmes Beach, FL 34217VRC16-000105Welcome to Simply Chic, an inviting ground-level vacation home with four bedrooms and three bathrooms just a quick walk from the sp

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Highlights• 5-minute walk from the beach• Private pool • Putting green, pool table, and ping pong table• Near restaurants and shops• Outdoor showerStormalong Bay by Anna Maria Island Accommodations 308 56th St Unit AHolmes Beach, FL 34217Welcome to Stormalong Bay, a beautiful two-bedroom, two-bath vacation home with a bonus room just a quick walk f

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Totally Beachin’ by AMI Locals2208 Ave A Bradenton Beach, Florida Welcome to Totally Beachin’, a timeless paradise with three bedrooms and three bathrooms just seconds from the Anna Maria Sound and a quick walk from the sparkling Gulf beach! This getaway has many features perfect for entertaining friends and family, including a private pool, a putt

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Sunsets and Daydreams by Anna Maria Island Accommodations 6250 Holmes Blvd, Unit 24 Holmes Beach, Florida Welcome to Sunsets and Daydreams! This multi-level villa offers a serene escape with two bedrooms, two and a half baths, and a tranquil downstairs patio enveloped by lush, tropical landscaping. Enjoy amenities including outdoor seating, a BBQ

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Sunsets and Daydreams

Beach Escape by AMI Locals789 Jacaranda Rd Anna Maria, FloridaVR18-000090Welcome to Beach Escape a luxury vacation home that is just one street from the sugary white sands of the Gulf of Mexico! Your resort-style backyard is perfect for all-day fun, play a few rounds of miniature golf and a competitive game of cornhole then jump in the beautiful pr

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Blue Lagoon 1 by Anna Maria Island Accommodations Holmes Beach Vacation Condo VRC16-000166Welcome to Blue Lagoon 1, a charming Poolside vacation condo just a two-minute walk from the white sands of Holmes Beach! Perfect for couples, friends, or small families, this condominium offers one bedroom and one and a half bathrooms, comfortably sleeping up

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