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 74 properties available
Shore Is Paradise by AMI Locals 315 N Bay Blvd, Anna Maria, Florida VR20-000087 Welcome to Shore Is Paradise, a modern four bedroom, four and a half bath home overlooking Bayfront Park on the north end of Anna Maria Island. Enjoy a private resort-style pool and spa, plus a rooftop deck with panoramic bay views and a putting green. You are a short
Hot HOT 11
Shore Is Paradise
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (5)
Acquaviva by Anna Maria Island Accommodations 310 Tarpon St, Anna Maria, Florida Welcome to Acquaviva, a stunning canal-front retreat that captures the essence of Anna Maria Island. This elegant three-bedroom, three-bath home offers a private dock for boating and wildlife watching, a sparkling pool, and a bonus game room. It's all just a short wal
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Acquaviva
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (11)
Bay Breezes at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #1, Anna Maria, FL 34216VR18-000088Welcome 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 the beautiful bay and minutes to Anna Maria beaches! This delightful coastal
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Bay Breezes at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 2 BR
Bathrooms 1 BA
Guests 6 guests
Rating 5 (64)
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 15
Turtle Crawl
Anna Maria
Bedrooms 2 BR
Bathrooms 2 BA
Guests 4 guests
Rating 5 (37)
Mangoes on Magnolia by Anna Maria Island Accommodations 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 convenience. With a priva
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Mangoes on Magnolia
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (13)
Bay View Bliss by AMI Accommodations 117 7th St N Unit 29, Bradenton Beach, FL 34217 Welcome to Bay View Bliss, a newly remodeled two-bedroom, one bath coastal condo tucked in the heart of Bradenton Beach. Just a block from the beach, steps from the bay, and less than a mile from the vibrant Bridge Street district, this ground floor unit is your pe
Hot HOT 17
Bay View Bliss
Bradenton Beach
Bedrooms 2 BR
Bathrooms 1 BA
Guests 4 guests
Rating 5 (2)
Jackie’s Cottage by Anna Maria Island Accommodations Holmes Beach Canal Front Retreat with Dock VRC18-000190Welcome to Jackie’s Cottage, a stunning one level canal front home with a private wet dock and dry dock, now showcasing recently updated interiors with modern furnishings and coastal decor. Just a block and a half from the pristine Gulf beac
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Jackie's Cottage
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (10)
Seahorse Paradise by Anna Maria Island Accommodations 311 68th St Holmes Beach VRC16-000108 Welcome to Seahorse Paradise, a beautiful vacation rental home just two and a half blocks from the beach! Pack your favorite beach toys and head to the warm sand and turquoise waters of the Gulf for the ultimate beach day. Then, hop on the Free Anna Mari
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Seahorse Paradise
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (18)
South Seas by Anna Maria Vacations 307 A 66th Street, Unit A, Holmes Beach, FL 34217 VRC16-000311 Welcome to South Seas, a show-stopping three-level vacation home just a 5-minute walk to Holmes Beach! With six spacious bedrooms, four and a half bathrooms, and a private pool with an incredible waterslide, this luxury retreat is perfect for family
Hot HOT 27
South Seas
Holmes Beach Pet Friendly
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (3)
Salty Soul by Anna Maria Island Accommodations 26 Seaside Ct, Holmes Beach, FL Welcome to Salty Soul, your family’s canal-front island escape located in beautiful Holmes Beach on Anna Maria Island! With two spacious bedrooms, two ensuite bathrooms, and a private dock, this charming single-level retreat is perfect for families or small groups lookin
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Salty Soul
Holmes Beach Pet Friendly
Bedrooms 2 BR
Bathrooms 2 BA
Guests 4 guests
Rating 5 (4)
Gulf View Beach House by AMI Locals 105 4th St N, Bradenton Beach, FLTPL18-000442Experience tranquility at Gulf View Beach House, a stunning retreat just minutes from Bradenton Beach’s white sands and turquoise waters! This luxurious five-bedroom, three-bath home features panoramic Gulf views from the living room, balconies, and rooftop deck. With
Hot HOT 21
Gulf View Beach House
Bradenton Beach Pet Friendly
Bedrooms 5 BR
Bathrooms 3 BA
Guests 15 guests
Rating 5 (66)
On the Flip Side by AMI Locals2210 Avenue A Bradenton Beach, FloridaTPL23-000007Welcome to On the Flip Side, a marvelous getaway with a rooftop deck that boasts water views and an outstanding backyard with a sparkling pool with custom built-ins and an in-ground spa. This home is tucked away in a beachy neighborhood near Tampa Bay and just a quick w
Hot HOT 11
On the Flip Side
Bradenton Beach Pet Friendly
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 16 guests
Rating 5 (24)

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