Anna Maria Island Featured Properties

Our Anna Maria Island Featured Properties showcase all of the best amenities and locations in Anna Maria Island and nearby Bradenton, Florida. Many offer a private pool or a rooftop deck, are close to the beaches, and have beautifully comfortable interiors that will ensure you enjoy every moment of your vacation! Our expert Reservations team is on standby to answer any questions, so please feel free to call us at 941-779-0733.


Properties Available 22 properties available
Gulf Shore Cottage by Anna Maria Island Accommodations 9206 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 c
Hot HOT 45
Gulf Shore Cottage
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 2 BA
Guests 8 guests
Rating 5 (15)
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
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Coconut Cove
Bradenton Beach Pet Friendly
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 14 guests
Rating 5 (76)
Shell We Dance by Anna Maria Island Accommodations 224 Chilson Ave, Anna Maria, FL 34216Experience the pinnacle of luxury on Anna Maria Island at Shell We Dance, part of our Exclusive Collection. This canal-front estate boasts six lavish bedrooms and six and a half bathrooms! Featuring a private pool, spa, rooftop deck with sweeping water views, an
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Shell We Dance
Anna Maria Pet Friendly
Bedrooms 6 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (6)
Addison’s Beach House by Anna Maria Island Accommodations Holmes Beach Family Beach Retreat with Pool VRC16-000188Welcome to Addison’s Beach House, your idyllic beach vacation escape just a three-minute walk from the breathtaking Holmes Beach of Anna Maria Island! This beautifully renovated, ground-level three-bedroom, two-bath home offers a tropic
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Addison's Beach House
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (30)
Hammock Dreams by Anna Maria Island Accommodations 131 Hammock Rd, Anna Maria, FL 34216 VR16-000408 Welcome to Hammock Dreams! Escape to the peaceful island lifestyle at Hammock Dreams, a stunning canal-front home nestled in the heart of Anna Maria. With three bedrooms, two bathrooms, and a private pool, this tropical retreat is ideal for families
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Hammock Dreams
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (8)
Carefree Cay by Anna Maria Island Accommodations 217 Sycamore Avenue, Anna Maria, FL, 34216 VR16-000412 Welcome to Carefree Cay, a spacious vacation home nestled in the desirable north end of Anna Maria Island. This three bedroom, two and a half bath retreat offers a private pool, in-ground spa, and lush outdoor living, perfect for families or gro
Hot HOT 44
Carefree Cay
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Bathrooms 1 Half Bath
Guests 6 guests
Rating 4.9 (31)
Highlights • Canal front • 5-minute walk to the beach • Rooftop deck • Private pool with in-ground spa • Outdoor living space Aqua Bay by Anna Maria Vacations 217 North Harbor Drive Holmes Beach, Florida Welcome to Aqua Bay! This luxurious canal-front home has four bedrooms and three bathrooms, providing guests with a relaxing and top-notch getaway
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Aqua Bay
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (16)
Beach Baby by Anna Maria Island Accommodations 704 Rose St Anna Maria, FL 34216VR16-000384Welcome to Beach Baby where you are only five houses away from the breathtaking gulf waters. This special two-story house offers a glorious backyard getaway with its heated pool, hot tub, and two inviting hammocks. Check out the ground level for some friendly
Hot HOT 35
Beach Baby
Anna Maria
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (25)
The Royal by AMI Locals 3015 Avenue E, Holmes Beach, FL 34217Experience luxury and island paradise at The Royal, part of our Exclusive Collection. This designer four-bedroom, five-and-a-half-bath beachfront home is just steps from the soft powder sands of Anna Maria Island! This three-level estate boasts a spectacular rooftop deck with panoramic oc
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The Royal
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 5 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (2)
Villa La Concha by Anna Maria Island Accommodations113 Maple Avenue, Anna Maria, FL, 34216VR16-000446Welcome to Villa La Concha, a luxurious six-bedroom, four-and-a-half-bath vacation rental just a one minute from the white sands of Anna Maria beach! Perfect for large families or groups, this coastal retreat features a private pool and hot tub, gam
Hot HOT 16
Villa La Concha
Anna Maria
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (37)
Social Nest by Anna Maria Island Accommodations 308 Pine Avenue, Anna Maria, FL 34216 Welcome to Social Nest, a charming three-bedroom, two-bath vacation home perfectly located on iconic Pine Avenue in the city of Anna Maria. This home is located directly above the popular Pizza Social shop right on Pine Avenue in the city of Anna Maria. This invit
Hot HOT 31
Social Nest
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 8 guests
Rating 5 (44)
Beach Escape by AMI Locals 789 Jacaranda Rd, Anna Maria, FL, 34216 VR18-000090 Welcome to Beach Escape, a stunning five-bedroom, four-bath luxury home just one street from the powdery white sands of Anna Maria Island. Ideally located on the peaceful north end near Bean Point Beach, this coastal retreat combines upscale comfort with endless outdoor
Hot HOT 20
Beach Escape
Anna Maria Pet Friendly
Bedrooms 5 BR
Bathrooms 4 BA
Guests 12 guests
Rating 5 (38)

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