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 31 properties available
Sail Away by AMI Locals 241 Willow Avenue, Anna Maria, Florida 34216 VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front luxury home in the heart of Anna Maria Island. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is des
Hot HOT 16
Sail Away
Anna Maria
Bedrooms 6 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (12)
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 19
Captain Ron's Beach Pad
Bradenton Beach
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (50)
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
Hammock Dreams
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (8)
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
Salty Seagull at Hunter's Point
Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Bathrooms 1 Half Bath
Guests 9 guests
Rating 4.9 (37)
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 18
Silver King
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (18)
Dolphin Daze by Anna Maria Island Accommodations 525 75th Street, Holmes Beach, FL 34217 VRC20-000001 Welcome to Dolphin Daze, a spacious five bedroom, four bath canal front vacation home in Holmes Beach, perfectly designed for unforgettable island getaways with family and friends. This Florida Gulf Coast rental features a private heated pool, sce
Dolphin Daze
Holmes Beach
Bedrooms 3 BR
Bathrooms 4 BA
Guests 6 guests
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 walk
Hot HOT 13
Acquaviva
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (15)
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 19
Tarpon Lookout
Bradenton Beach
Bedrooms 5 BR
Bathrooms 5 BA
Bathrooms 1 Half Bath
Guests 10 guests
Rating 5 (47)
Palm Gables 110 by Anna Maria Vacations 110 36th St, Holmes Beach, FL 34217 VRC16-000126 Welcome to Palm Gables 110, a rare Gulf-front three-bedroom, two-bathroom condo perfectly situated in the heart of Holmes Beach on beautiful Anna Maria Island! With bold tropical decor, stunning panoramic views of the ocean, and a private balcony that puts you
Hot HOT 13
Palm Gables 110
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 4.9 (42)
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 10
Anna Maria Wave
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Rating 5 (3)
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 12
Jackie's Cottage
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (11)
Salt Life by AMI Locals 112 11th St S, Bradenton Beach, Florida TPL 18-000551 Welcome to Salt Life by AMI Locals, a breathtaking five bedroom, five a half bath bayfront retreat located on the serene south end of Bradenton Beach. Perfect for families, boaters, and beach lovers, this luxury home offers the ultimate Anna Maria Island vacation rental e
Salt Life
Bradenton Beach Pet Friendly
Bedrooms 5 BR
Bathrooms 5 BA
Bathrooms 1 Half Bath
Guests 11 guests
Rating 5 (42)

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