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 16 properties available
Called in Sic by Anna Maria Island Accommodations 813 Jacaranda Rd, Anna Maria, Florida 34216 VR18-000103 Welcome to Called in Sic, a stunning and newly renovated four bedroom, three bath luxury vacation home located just one block from Bean Point Beach access on the peaceful north end of Anna Maria Island! With a private heated pool and spa, rooft
Hot HOT 11
Called In Sic
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (48)
Santorini by Anna Maria Island Accommodations 111 9th St. N, Bradenton Beach, FL, 34217 Welcome to Santorini, a charming two bedroom, one and a half-bath cottage that blends Greek-inspired style with Florida’s coastal charm. Just a three-minute walk to the white sands of Bradenton Beach, this cottage is ideally located near local restaurants, shops
Santorini
Bradenton Beach Pet Friendly
Bedrooms 2 BR
Bathrooms 1 BA
Bathrooms 1 Half Bath
Guests 5 guests
Rating 5 (5)
Shore Is Paradise by AMI Locals 315 N Bay Blvd, Anna Maria, Florida VR20-000087 Welcome to Shore Is Paradise, a beautifully designed four-bedroom, four and a half bath vacation home overlooking Bayfront Park on the north end of Anna Maria Island. With sweeping bay views, a private pool and spa, and a two-level rooftop deck with a putting green, th
Shore Is Paradise
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (5)
Gypsy Sol by Anna Maria Island Accommodations 516 Loquat Dr, Anna Maria, FL, 34216 VR18-000034 Welcome to Gypsy Sol, your ultimate Anna Maria Island escape! This four bedroom, two bath canal front vacation home is packed with fun and relaxation, featuring a private pool, hot tub, and ping pong table for endless entertainment. Just a short stroll f
Gypsy Sol
Anna Maria
Bedrooms 4 BR
Bathrooms 2 BA
Guests 8 guests
Rating 5 (27)
Ainsley Beach House by Anna Maria Island Accommodations 209 55th St, Holmes Beach, FL 34217 VRC16-000185 Welcome to Ainsley Beach House, a charming three-bedroom, two-bath vacation home perfectly situated in the heart of Holmes Beach on Anna Maria Island. Just a five-minute stroll from the powder soft Gulf beaches, this inviting coastal retreat off
Hot HOT 17
Ainsley Beach House
Holmes Beach Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (41)
Our Tern by Anna Maria Island Accommodations 111 Tern Dr, Anna Maria, Florida 34216 VR22-000023 Welcome to Our Tern, a gorgeous canal front vacation home on the north end of Anna Maria Island! This three bedroom, three and a half bath retreat offers a private dock, sparkling pool and hot tub, and multiple outdoor living spaces, making it the perfec
Hot HOT 13
Our Tern
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 6 guests
Rating 5 (18)
Beach Breeze by AMI Locals 205 Elm Ave, Anna Maria, FL 34216 VR16-000510 Welcome to Beach Breeze by AMI Locals, a vibrant four bedroom, three bath coastal retreat perfectly situated in the heart of Anna Maria Island. Just a two-minute walk to the beach and two minutes from Pine Avenue’s charming shops and restaurants, this home combines island styl
Hot HOT 13
Beach Breeze
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 3 BA
Guests 10 guests
Rating 5 (44)
Periwinkle Place by Exclusive Vacations 226 Periwinkle Plaza, Anna Maria, FL 34216 VR25-000004 Indulge in the ultimate luxury beach home at Periwinkle Place, part of our Exclusive Collection. This stunning estate in the heart of Anna Maria offers six spacious bedrooms and six and a half bathrooms. Just a five-minute walk from the pristine shoreline
EXCLUSIVE COLLECTION EXCLUSIVE COLLECTION
EXCLUSIVE COLLECTION
Periwinkle Place
Anna Maria Pet Friendly
Bedrooms 6 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (2)
Just Beachy by AMI Locals 211 65th St, Holmes Beach, Florida 34217 VRC19-000141 Welcome to Just Beachy by AMI Locals, a beautifully designed 6-bedroom, 4.5-bath luxury beach home just a 2-minute walk from the Gulf shores of Anna Maria Island. Nestled in the heart of Holmes Beach, this coastal chic retreat blends elegant design with family-friendly
Just Beachy
Holmes Beach Pet Friendly
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (34)
Island Mojo by Anna Maria Island Accommodations 312 58th St, Holmes Beach, FL 34217 VRC16-000143 Welcome to Island Mojo, a charming three bedroom, two bathroom ground-level home just eleven minutes from the Gulf. Perfectly located near parks, restaurants, shops, and the island trolley, this cozy coastal retreat features a private heated pool, relax
Hot HOT 27
Island Mojo
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (24)
North End Zen by Anna Maria Island Accommodations 112 Hammock Rd, Anna Maria, FL 34216 VR16-000360 Welcome to North End Zen, a newly renovated four-bedroom, three-bath canal front retreat just a five-minute walk to Anna Maria Beach and steps from Pine Avenue’s boutique shops, cafes, and waterfront dining. Perfect for families and groups, this Anna
Hot HOT 19
North End Zen
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (28)
Margarita-Ville by Anna Maria Island Accommodations 121 46th Street, Holmes Beach, FL 34217VRC16-000136Experience the ultimate island escape at Margarita-Ville, a stunning six-bedroom, four and a half bath vacation home designed for large families or groups seeking a memorable getaway! Just a two-minute walk from the beach, this beautifully landsca
Hot HOT 23
Margarita-Ville
Holmes Beach
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (21)

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