Anna Maria Island Waterfront Rentals

Waterfront Vacation Homes on Anna Maria Island...

Anna Maria Island is known for its beautiful beaches and family oriented atmosphere. We have a stellar selection of waterfront vacation rentals for you to choose from. Canalfronthomes are perfect for those families looking for some additional fun things to do as you can boat, paddleboard, or fish right from your own backyard. Bayfront vacation rentals, with the skyway bridge as their backdrop, offer unique views and an immersion into the surrounding nature.


Properties Available 29 properties available
Anna Maria Wave by Anna Maria Island Accommodations 2806 Avenue E, Holmes Beach, FL 34217 Welcome to Anna Maria Wave by Anna Maria Island Accommodations, a spectacular four-bedroom, four-bathroom beachfront home that captures the essence of coastal luxury on beautiful Anna Maria Island. Perfect for families and groups, this contemporary retreat com
Hot HOT 32
Anna Maria Wave
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Rating 5 (2)
Captain Ron's Beach Pad by Anna Maria Island Accommodations Bradenton Beach Gulf Front Rental Welcome to Captain Ron's Beach Pad, a stunning beachfront home directly on Bradenton Beach. This inviting ground-level retreat features two bedrooms and two bathrooms, comfortably sleeping up to six guests. With breathtaking Gulf views from your private pa
Hot HOT 67
Captain Ron's Beach Pad
Bradenton Beach
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (50)
Highlights• Beachfront • Outdoor kitchen area• Pool and hot tub• Private beach access• ElevatorTarpon Lookout by Anna Maria Island Accommodations2302 Gulf Dr NBradenton Beach, FL 34217TPL18-000468The ultimate beachfront vacation awaits you at Tarpon Lookout, a luxury five-bedroom and five-and-a-half bathroom getaway with private beach access, a gul
Hot HOT 31
Tarpon Lookout
Bradenton Beach
Bedrooms 5 BR
Bathrooms 5 BA
Bathrooms 1 Half Bath
Guests 10 guests
Rating 5 (43)
Seaside Serenity by Anna Maria Island Accommodations 301 Bay Dr N, Bradenton Beach, FL 34217 Welcome to Seaside Serenity, a charming 2-bedroom, 1 bath bayfront cottage in Bradenton Beach. The second story living space is perched directly on the water with a private dock and panoramic sunrise views, this Florida-style home is perfect for guests seek
Hot HOT 36
Seaside Serenity
Bradenton Beach
Bedrooms 2 BR
Bathrooms 1 BA
Guests 7 guests
Rating 5 (15)
Sea Swept by Exclusive Vacations 2516 Gulf Dr N, Bradenton Beach, FL 34217 TPL22-000035 Welcome to Sea Swept, part of our Exclusive Collection. This beachfront luxury home boasts ten-bedrooms, eight-and-a-half-baths with breathtaking Gulf views, private beach access, and resort-style amenities. Located just steps from the pristine beaches, this h
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EXCLUSIVE COLLECTION
Sea Swept
Bradenton Beach Pet Friendly
Bedrooms 10 BR
Bathrooms 8 BA
Bathrooms 1 Half Bath
Guests 20 guests
Rating 4.9 (34)
Banyan Manor by Anna Maria Island Accommodations 219 Chilson Ave, Anna Maria, FL 34216 VR20-000064 Welcome to Banyan Manor, a stunning canal front vacation home on the north end of Anna Maria Island. With four bedrooms, four bathrooms, a private 50-foot dock, and a resort style backyard, this luxury retreat is perfect for families and groups seekin
Hot HOT 62
Banyan Manor
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Rating 4.9 (31)
Bay View Beauty by Exclusive Vacations 881 N Shore Dr, Anna Maria, FL 34216 VR18-000097 Welcome to Bay View Beauty, part of our Exclusive Collection. This luxurious seven-bedroom, seven and a half bath beachfront home with direct beach access and unobstructed bay views. Ideally located along Anna Maria’s North Shore Drive, this luxury retreat place
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EXCLUSIVE COLLECTION
Bay View Beauty
Anna Maria Pet Friendly
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 16 guests
Rating 5 (61)
Highlights • Canal front with private dock• Less than a 10-minute walk to the beach• Private pool with in-ground spa• Poolside bar• ElevatorBayshores by Anna Maria Island Accommodations228 S Harbor DrHolmes Beach, FL 34217VRC18-000040Step into a slice of Old Florida at Bayshores, a charming three-bedroom, three-bathroom canal front retreat nestled
Hot HOT 30
Bayshores
Holmes Beach
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (38)
Jackie’s Cottage by Anna Maria Island Accommodations 209 N Harbor Dr, Holmes Beach, FL, 34217VRC18-000190Welcome 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 beaches
Hot HOT 31
Jackie's Cottage
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (10)
Silver King by Anna Maria Island Accommodations 316 Tarpon Street, Anna Maria, FL 34216 VR16-000118 Welcome to Silver King, a stunning four-bedroom, three-bathroom canal-front vacation home with a bonus bunk room, rooftop deck, and a backyard designed for endless fun. Located just four blocks from the Gulf beaches and three blocks from the charming
Hot HOT 51
Silver King
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (17)
Honeywood House by Anna Maria Island Accommodations 243 Willow Ave, Anna Maria, FL 34216 Welcome to Honeywood House, a canal-front three-bedroom, four-bath vacation home with a private dock, pool, and spa. Located on scenic Bimini Bay, this pet-friendly retreat offers direct access to Tampa Bay by boat and is just a short ten-minute walk to the Gul
Hot HOT 27
Honeywood House
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (10)
Our Tern by Anna Maria Island Accommodations111 Tern Dr, Anna Maria, Florida 34216VR22-000023Welcome 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 perfect s
Hot HOT 40
Our Tern
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 6 guests
Rating 5 (15)

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