Anna Maria Island Vacation Rentals

Anna Maria Island Vacation Rentals

Duncan Vacation Rentals is your Anna Maria Island vacation rentals expert, servicing the Florida Gulf Coast Island cities of Anna Maria, Holmes Beach, Bradenton Beach, Longboat Key, and the surrounding area. 

Duncan Real Estate offers the best Anna Maria Island Vacation Rentals.

Relax and enjoy the sun and sand as you fully immerse yourself in the island's laid-back atmosphere. Have a memorable vacation with friends and family as you

Explore local shops and restaurants in Anna Maria Island or simply spend your days lounging on the pristine beaches.

Our rentals range from cozy cottages to luxury Beachfront Rentals. Whether you're looking for a peaceful retreat or an action-packed vacation, Duncan Real Estate has the rental for you.

Want to bring your pet on your next vacation? Browse our Anna Maria Island Pet Friendly Rentals.


Filter by pool, location, bedrooms and more! Our rentals are fully furnished and equipped with amenities to make your vacation hassle-free and enjoyable.

Our team is dedicated to providing exceptional customer service and ensuring a smooth booking process. We are available to answer any questions or address any concerns during your stay.

Don't wait to experience the beauty of Anna Maria Island. Book online your dream vacation rental. We look forward to having you stay with us on this paradise island.



View All Anna Maria Island Vacation Rentals


Properties Available 104 properties available
Casual yet luxurious, this three-bedroom duplex with a private, heated pool and close proximity to the beach is the perfect choice for vacationers to relax and unwind when visiting Anna Maria Island. Your favorite dog is also invited for a small pet fee (30 lbs. max, please!). Sapphire Beach House is located two blocks from the powdery sand on Holm
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Sapphire Beach House
Duplex - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
THE SALTED COCONUTThe Salted Coconut is just a short stroll to the beautiful beaches of Anna Maria! This gorgeous home is a 3-bedroom, 3-bath with a private, heated pool. There is plenty of room to host 8 guests. The ground level floor plan makes it easy to take advantage of the backyard. The pool area is very inviting with the sun on it throughout
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The Salted Coconut
Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (7)
Welcome to Island Escape! This home is a beautifully decorated, newly remodeled two-bedroom, two-bathroom vacation duplex in the heart of Holmes Beach. In this convenient ground level layout guests will enjoy a well-equipped kitchen perfect for preparing a gourmet meal or cook outdoors on the gas grill. Island Escape is a very short walk from the b
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Island Escape
Duplex - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (5)
Looking for a great vacation location on beautiful Holmes Beach, then look no further. This newly renovated light & bright private 2-bedroom, 2-bathroom home features a great floor plan complete with brand new heated pool with spa & sun-shelf, game room, full size washer / dryer, cable TV, Wi-Fi and so much more. This tropical retreat and luxuriou
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Lazy Pelican
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Lazy Pelican
Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (1)
NORTH BEACH ISLAND TREE HOUSEWelcome to North Beach Island Tree House! With pure privacy and a close stroll to the beach! Sleeps six in three bedrooms, with two full bathrooms and outdoor shower. Luxury at an affordable price. Private location with exotic, tropical landscaping, and a nice variety of palm trees. Less than a two-minute walk to the b
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North Bch Isl Tree House
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North Bch Isl Tree House
Duplex
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Welcome to The Getaway which is in a complex that is located just across the street from the white sandy beaches of Anna Maria Island! The Getaway is a beautifully renovated and updated 2-bedroom, 2-bath Townhouse condo. This spacious first and second floor rental invites to a pleasant beach vacation with its superb location. The complex with its G
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The Getaway
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (1)
This casual and comfortable three-bedroom duplex comes with a private, heated pool. And proximity to the beach with no streets to cross to reach the beach access! A convenient location close to the heart of Holmes Beach is the perfect choice for vacationers to relax and unwind when visiting Anna Maria Island. With coastal decor, an open floor plan,
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7 Doors Down
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7 Doors Down
Duplex - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Gladiolus on the Water was recently updated with a brand-new master suite. Enjoy new furnishings and fresh paint, all tied together with a festive and tropical theme! The convenient ground level layout accommodates up to 6 g
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Gladiolus on the Water
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (4)
Welcome to Cayman Cay 201 which is in a complex that is located just across the street from the white sandy beaches of Anna Maria Island! Cayman 201 is a beautifully updated and comfortable 2-bedroom, 2-bath condo. This spacious second floor rental invites to a pleasant beach vacation with its superb location. The complex with its Gulf Drive addres
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Cayman Cay 201
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Rating 5 (4)
Please contact us for a detailed pricing quote and to book!Splurge yourself in this luxurious ground level on beautiful Anna Maria Island only a few steps away from the white beach. The perfectly maintained, marvelous private custom-built vacation rental home features 6 bedrooms, 4.5 bathrooms and can accommodate up to fourteen people. The ground l
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AMI Beach House
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AMI Beach House
Home
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Pool pool
Rating 5 (5)
Welcome to Coquina Cottage A! Family friendly Coquina Cottage A is exceptionally located at the northern end of Anna Maria Island, just steps away from gorgeous Tampa Bay. Enjoy water views from this two-bedroom, groundlevel, two-story duplex home across from the calm waters and playground amenities of Bayfront Park. Walk to catch the free trolley,
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Coquina Cottage A
Duplex
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (4)
Welcome to "Spring Break"! This property is located on the North end of the Anna Maria Island and has a wonderful private, heated pool. Conveniently close to the beach to enjoy the sunset view from the front porch and a short walk of 176 yards to the white sand of the Gulf of Mexico. Just pass a few homes and stick your toes in the water or dine at
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Spring Break
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pool pool
Rating 5 (7)

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