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.

Properties Available 232 properties available
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
Hot HOT 16
Flip Flops and Fish Tales
Flip Flops and Fish Tales
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (6)
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Boundless Waves by Anna Maria Island Accommodations 408 Magnolia Ave, Anna Maria, FL Welcome to Boundless Waves, part of our Exclusive Collection. Offering a curated luxury experience with elevated amenities, personalized services, and refined island living. This six-bedroom, six-and-a-half-bath coastal retreat features a rooftop deck with panoram
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EXCLUSIVE COLLECTION
Boundless Waves
Boundless Waves
Anna Maria Pet Friendly
Bedrooms 6 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (6)
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Absolutely Anna by Anna Maria Island Accommodations 805 N Bay Blvd Anna Maria, FL 34216 VR16-000095 Escape to paradise at Absolutely Anna, just a stone's throw away from the stunning Bean Point Beach. With the warm waters of the Gulf of Mexico a mere 5-minute walk away, this vacation home is a dream come true for beach lovers.Highlights• Less than
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Absolutely Anna
Absolutely Anna
Anna Maria Pet Friendly
Bedrooms 2 BR
Bathrooms 2 BA
Guests 5 guests
Rating 5 (32)
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Coconut Cottage by Anna Maria Island Accommodations 310 68th St, Holmes Beach, FL 34217VRC16-000159Welcome to Coconut Cottage, a stunning coastal retreat just a quick stroll from the turquoise ocean of Holmes Beach! Perfect for families and groups seeking fun and relaxation. This three-bedroom, two and a half bath home offers a private heated pool,
Hot HOT 31
Coconut Cottage
Coconut Cottage
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Bathrooms 1 Half Bath
Guests 6 guests
Rating 5 (19)
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Beach Cottage by Anna Maria Island Accommodations 211 71st St, Holmes Beach, FL 34217 VRC16-000178 Welcome to Beach Cottage, a charming ground-level vacation home in Holmes Beach, just a 3-minute walk to the white sands of the Gulf beaches. With four bedrooms, three bathrooms, and a private pool and spa, this coastal retreat is ideal for families a
Hot HOT 50
Beach Cottage
Beach Cottage
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (35)
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It’s a Jungle Out There by Anna Maria Island Accommodations 4002 5th Ave, Holmes Beach, FL 34217 VRC19-000173 Welcome to It’s a Jungle Out There by Anna Maria Island Accommodations, a breathtaking six bedroom, three and a half bath luxury retreat located in the heart of Holmes Beach, just a short stroll from the white sand shores of the Gulf. This
Hot HOT 19
It's a Jungle Out There
It's a Jungle Out There
Holmes Beach
Bedrooms 6 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (28)
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Deckadance by AMI Locals407 N Bay Blvd. Anna Maria, FL 34216Experience the ultimate getaway at Deckadance! This brand-new luxury rental features 4 bedrooms and 4.5 bathrooms, making it the perfect choice for families or groups looking to indulge in the beauty of Anna Maria Island. Just across the street, you’ll find pristine bay beaches and the nea
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EXCLUSIVE COLLECTION
Deckadence
Deckadence
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (3)
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Ohana by Anna Maria Island Accommodations 4807 2nd Ave, Holmes Beach, FL 34217Experience the perfect family vacation at Ohana, a stunning four-bedroom, three and a half bath home just a three-minute walk from the white sands and turquoise waters of Holmes Beach! This beautifully furnished home features a private pool shaded by graceful palms, an o
Hot HOT 27
Ohana
Ohana
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (3)
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Turtle Crawl by Anna Maria Island Accommodations 763 Jacaranda Rd, Unit B, Anna Maria, FL 34216VR16-000350Welcome to Turtle Trax, a cozy ground-level duplex tucked away in the peaceful north end of Anna Maria Island. Just a five-minute walk to the beach, this two-bedroom, two-bath vacation rental offers a shared backyard pool surrounded by lush lan
Hot HOT 12
Turtle Crawl
Turtle Crawl
Anna Maria
Bedrooms 2 BR
Bathrooms 2 BA
Guests 4 guests
Rating 5 (37)
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Bay Vista at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #5, Anna Maria, FL 34216 VR18-000088 Welcome to Bay Vista at Bayside Bungalow, a three bedroom, two bath condo located in Anna Maria. With panoramic 180° water views, this coastal retreat offers front-row seats to dolphins, sailboats, and spectacular sunrises. Just steps from the Bays
Hot HOT 12
Bay Vista at Bayside Bungalow
Bay Vista at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (102)
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Highlights • 3-minute walk from Beach • Private pool and hot Tub • Outdoor shower • Washer and dryerBeach You To It by Anna Maria Accommodations 206 Palm Ave Anna Maria, FL 34216VR18-000150Welcome to Beach You To It, a stunning vacation rental home located just a block away from the beach! Grab your beach gear must-haves and check out the nearest b
Hot HOT 27
Beach You To It
Beach You To It
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (50)
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Barefoot by the Bay at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #3, Anna Maria, FL 34216VR18-000088Welcome to Barefoot by the Bay, a luxury ground-level villa offering one bedroom, two bathrooms, and a cozy den in a picturesque bayside setting! Located just across the street from beautiful Bay and within walking distance of the beach, re
Hot HOT 29
Barefoot by the Bay at Bayside Bungalow
Barefoot by the Bay at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 1 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (72)
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