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
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 5 (26)
Lavender Lagoon by Anna Maria Island Accommodations 123 Crescent Dr, Anna Maria, FL 34216VR22-000006Welcome to Lavender Lagoon, a beautiful canal front three-bedroom, two-bath vacation home tucked in the heart of Anna Maria. This waterfront retreat offers a private pool and spa, screened lanai, a backyard putting green, and a private dock ideal fo
Hot HOT 33
Lavender Lagoon
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (12)
The Curated Palm by Anna Maria Island Accommodations 520 Kumquat Drive, Anna Maria, FL 34216 Welcome to The Curated Palm, a four bedroom, four and a half bath luxury canal-front home designed for multi-family vacations, group getaways, and extended stays. This stunning retreat offers resort-style outdoor living with a private saltwater pool, oversi
Hot HOT 44
The Curated Palm
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (4)
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 17
Honeywood House
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (10)
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
EXCLUSIVE COLLECTION EXCLUSIVE COLLECTION
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)
Bayfront Paradise by AMI Locals 238 S Harbor Dr, Holmes Beach, FL VRC18-000090 Welcome to Bayfront Paradise by AMI Locals, a spectacular 5-bedroom, 4.5-bathroom canal-front luxury home offering panoramic views of the Bay. Located in a quiet residential area of Holmes Beach, this coastal retreat combines elegance, relaxation, and adventure. With a p
Hot HOT 17
Bayfront Paradise (AMIL)
Holmes Beach Pet Friendly
Bedrooms 5 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (29)
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 41
North End Zen
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (28)
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)
Triple Play by Anna Maria Island Accommodations 313 Iris Street, Anna Maria, Florida VR16-000416 Welcome to Triple Play, a canal-front 3-bedroom, 3-bath vacation home where you can enjoy three perfect ways to relax: a short walk to the beach, a refreshing dip in your private pool and spa, or fishing and kayaking right from your own docks. Located j
Hot HOT 41
Triple Play
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (30)
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 52
Captain Ron's Beach Pad
Bradenton Beach
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (50)
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
Hot HOT 24
Aqua Bay
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (16)
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
Hot HOT 31
Hammock Dreams
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (8)

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