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
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 54
Captain Ron's Beach Pad
Bradenton Beach
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (50)
Salty Seagull at Hunter’s Point by AMI Locals 4321 Marina View Way, Cortez, FL 34215 Enjoy an unforgettable island escape at Salty Seagull at Hunter’s Point, a brand new canal front vacation home just one mile from Anna Maria Island’s iconic beaches. This three bedroom, two and a half bath residence is located in an exclusive new sustainable commun
Hot HOT 10
Salty Seagull at Hunter's Point
Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Bathrooms 1 Half Bath
Guests 9 guests
Rating 5 (26)
Coco Cottage by Anna Maria Island Accommodations 113 Los Cedros Dr, Anna Maria, FL, 34216 Welcome to Coco Cottage, a welcoming 3 bedroom, 3 bath canal-front home designed for easy island living. Located just a 4-minute walk to Anna Maria Beach and moments from the shops and restaurants along Pine Avenue, this relaxing getaway blends coastal comfort
Hot HOT 17
Coco Cottage
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (4)
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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Sea Swept
Bradenton Beach Pet Friendly
Bedrooms 10 BR
Bathrooms 8 BA
Bathrooms 1 Half Bath
Guests 20 guests
Rating 4.9 (34)
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)
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 40
North End Zen
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (28)
Dolphin Daze by Anna Maria Island Accommodations Holmes Beach Canalfront Home with Pool VRC20-000147Welcome to Dolphin Daze, a stunning canal front vacation home with a dock and private heated pool, just a thirteen-minute walk from Holmes Beach! This spacious three-bedroom, four-bath getaway sleeps up to six guests. Perfect for families and friends
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Dolphin Daze
Holmes Beach
Bedrooms 3 BR
Bathrooms 4 BA
Guests 6 guests
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
Hot HOT 36
Salty Soul
Holmes Beach Pet Friendly
Bedrooms 2 BR
Bathrooms 2 BA
Guests 4 guests
Rating 5 (4)
Highlights •Located directly on the Bay•Rooftop Deck with Panoramic Bay and Gulf Views•Exciting Backyard Putting Green•7-minute walk to Beach Access•Elevator for Guest convenience•Dog friendly with approval and additional fee•Outdoor Grill, Dining Area and Living Area•Resort Style Pool and Spa Overlooking the Bay•Close Proximity to Historic Bridge
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Big Nauti
Bradenton Beach Pet Friendly
Bedrooms 8 BR
Bathrooms 8 BA
Bathrooms 1 Half Bath
Guests 18 guests
Rating 5 (17)
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)
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 37
Banyan Manor
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Rating 4.9 (31)
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 41
Anna Maria Wave
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Rating 5 (2)

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