Anna Maria Island Vacation Rentals

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 or simply spend your days lounging on the pristine beaches.

Our rentals range from cozy beach 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.

Browse by pool, pet friendly, 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.


Properties Available 34 properties available
Welcome to Flamingo Bay! This beautiful waterfront home with private bay beach and steps to the City Pier! New up-dates! New tiled flooring through the whole property and some up-dates. Absolute waterfront house on the bayside on the north end of Anna Maria. A spacious four bedroom/three-and-a-half-bathroom beach house. The master suite expands the
Hot HOT 34
Flamingo Bay
Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
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
Hot HOT 25
Gladiolus on the Water
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (4)
Emerald Surf is a newly remodeled three-bedroom, two-bathroom canal front home with a pool in the city of Anna Maria. This fabulous house is only 2 short blocks to the white sand beaches of Anna Maria Island and a short walk to the restaurants and shops on Pine Avenue. The easy ground level living offers a large living room with plush seating for t
Hot HOT 29
Emerald Surf
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (4)
Sunrise Vista is an Old Florida, vintage beach cottage, steps away from Tampa Bay. The house, which has been in the same family for three generations, is perfect for couples or small families that love a "close to nature beach" experience. We know you will love and experience the magic that Anna Maria holds while staying at Sunrise Vista.Surrounded
Hot HOT 19
Sunrise Vista
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)
Nestled on the far North end of Anna Maria right at Bean Point, is Seascapes, newly remodeled three- bedroom, two-bathroom vacation home directly across from the Beach. This property has direct access to the Gulf and is closer to the water than many of the Beach front homes on the Island! With direct access right out the front door, you can be on a
Hot HOT 19
Seascapes
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Welcome to Coquina Cottage! Relax stress-free in this two-bedroom ground level duplex accommodation with water views, across from Bay Front Park and within walking distance of Bean Point, gulf beaches, restaurants, bars, and shopping on Pine Avenue. Coquina Cottage is on the north-end of the Island in the City of Anna Maria. Enjoy the views of the
Hot HOT 19
Coquina Cottage A
Duplex
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (4)
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
Hot HOT 27
The Salted Coconut
Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (6)
Welcome to Pier to Pier Paradise! This beautiful newer luxury home is one of a kind! Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach and a short walk from the Rod and Reel pier, the city pier, and Pine Avenue. Professionally decorated with av
Hot HOT 39
Pier To Pier Paradise
Home
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Pool pool
Rating 5 (5)
Welcome to Bayside Bliss which is a fully remodeled three-bedroom/three-bathroom, ground level cottage north of Pine Avenue in the City of Anna Maria. Enjoy easy Island life surrounded by tropical landscaping. It sleeps up to 8 guests. The open floor plan streamlines the living area, kitchen, and dining room. There is plenty of seating in the larg
Hot HOT 129
Bayside Bliss
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (5)
Nestled on the far North end of Anna Maria Island, with the beach cottage is just around the corner, The Lady Fish is a three-bedroom, two-bathroom vacation home. The closest beach access is just around the corner at Cypress Avenue. There is no direct path to the water from the backyard. Come home from a sunny day on the shores of the Gulf of Mexic
Hot HOT 41
The Lady Fish
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Here it is - the ‘Old Florida’ charm you’ve been looking for! Relax stress-free in this two-bedroom attached villa, within walking distance of beach, Bay, restaurants, bars, shopping, and more. Latitude Adjustment has been recently updated throughout with all new appliances and fixtures. Everything is geared to creating ‘home away from home’ comfor
Hot HOT 12
Latitude Adjustment
Duplex - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
West O' Gulf is a mere 212 steps to the beach and the crystalline Gulf of Mexico! As you take your short walk to the Gulf beaches, you will take in the sights of the dense banyans, spectacular homes of Park Avenue, and the tropical sea grapes. West O' Gulf is perfectly located - West of Gulf Drive, walking distance to shops and restaurants yet not
Hot HOT 40
West O'Gulf
Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (5)

Tell us what you're looking for and someone will contact you with available options.

I agree