Featured Vacation Rentals

Featured Vacation Rentals For A Perfect Florida Gulf Coast Vacation!

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 of Manatee County

Duncan Real Estate distinguishes itself from other Anna Maria Island vacation rentals with our personal touch. Experience the Duncan difference and find out why many of our guests return year after year. We strive to make your Anna Maria vacation the best one yet. As you begin to plan your Anna Maria Island vacation, it starts with ease over the phone where you talk to one of our local vacation rental agents that know all the properties and can help plan your trip. If you prefer online booking, start the reservation process by searching for your perfect Anna Maria Island getaway.

Don’t Miss out on Anna Maria Island Vacation Rentals Deals!

Make sure to browse our Online Specials. Duncan Deals are changing often and you do not want to miss a good deal!

New properties join our program all the time, so be sure to check out our Featured Vacation Rentals for the latest additions. Oftentimes introductory rates with special pricing are offered on the brand new Anna Maria Island vacation rental properties.

If you like to keep up to date with all Duncan Real Estate and Anna Maria Island news, sign up for our newsletter. Be the first one to know what is happening on beautiful Anna Maria Island!


Anna Maria Island Vacation Rentals Duncan Benefits

Duncan Vacation Rentals cooperates with island vendors to ensure you have everything you need while in paradise. Check out our Duncan V.I.P. perks and use your Duncan Real Estate guest promo code to enjoy special pricing while you are on your Anna Maria Island vacation!

Upon check in, we provide you with arrival information in addition to the guest handbook in every property. Find useful information about the house and Anna Maria Island. If you encounter any concerns during your stay, Duncan Vacation Rentals has their own maintenance staff to address your issues. Just give us a call and we are happy to help! Our emergency line is open 24/7. We encourage our guests for feedback on their stay with a short guest survey. This ensures us and our owners that we provide the best service possible.

Our return guests love the repeat discount! Be sure to mention it when you book with Duncan Vacation Rentals again.

Contact one of our professional vacation rental specialists today! We love to help you plan your perfect Anna Maria Island vacation getaway on the Gulf of Mexico. There’s nothing quite like walking out your front door and finding yourself toes deep in the magnificent white sand of our shoreline. Duncan Vacation Rentals is ready to serve your every beach holiday need, call today 941-779-0304 or email us.


View All Featured Vacation Rentals



Properties Available 16 properties available
Welcome to Hibiscus Villa! A canal front home in the heart of Anna Maria. Situated within easy walking distance of all three beaches, Bean Point; the Sandbar beach and Bay Front beach. Plus, the famous Rod and Reel Pier, City Pier and Pine Avenue with its shops, bars and restaurants.Hibiscus Villa is new to the rental market and provides perfect f
Hot HOT 59
Hibiscus Villa
Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (1)
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 120
Bayside Bliss
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (7)
Welcome to The Beach House 2! Enjoy absolute beachfront on the north end of Anna Maria. Directly on the Gulf of Mexico, north of Pine Avenue on beautiful Anna Maria Island, The Beach House 2 is a spectacular beach retreat. This Old Florida beach house on the outside, the interior has been remodeled and updated with all the comforts of a family home
Hot HOT 57
The Beach House 2
Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Only a block from the beach, Ahoy Matey is the perfect ground-level vacation rental home. This home is a two-bedroom, two-bathroom home that can comfortably accommodate up to six guests. The open floor plan provides a warm, welcoming atmosphere to relax with your friends and/or family. With a private, heated pool and an outdoor shower, Ahoy Matey h
Hot HOT 105
Ahoy Matey
Duplex
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Welcome to Surf Riders which is a fully remodeled four-bedroom/four-bathroom, cottage on the westside of Gulf Drive in the City of Holmes Beach. The property sleeps up to 8 guests. The downstairs is an open floor plan streamlines the living area, kitchen, and dining room. There is plenty of seating in the large living room with its large flat scree
Hot HOT 51
Surf Riders
Home
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Pool pool
Welcome to Veselka! The Island’s Rainbow. Enjoy this canal front home with dock and easy boat access to the intercoastal waters of Anna Maria, gulf breezes, island living and sea air from this stunning, newly renovated beach home located in the award-winning island of Anna Maria. Veselka offers four bedrooms and three bathrooms and can accommodate
Hot HOT 49
Veselka
Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Welcome to Maritime Memories! This north-end 3 bedroom, 2 bath pool home is waiting for you to enjoy your next vacation on Anna Maria Island. Maritime Memories is an eclectic island home with plenty of room for a large family, two living areas plus den so the house comfortably sleeps 8 people. Relax by the pool and enjoy the privacy of a tropica
Hot HOT 39
Maritime Memories
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pool pool
Welcome to Bodacious Oasis! This beautiful 4 bedroom 2 and 1/2 bath property can accommodate 8 guests very comfortably inside and out. Larger families will enjoy the open floor plan, providing plenty of room to spread out and enjoy comfortable island style furnishings and entertainment features.Pretty quilts are just the beginning when it comes to
Hot HOT 40
Bodacious Oasis
Home
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pool pool
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
Hot HOT 30
The Getaway
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (1)
Welcome to Playa Encantada 205, a supreme Anna Maria Island Gulf front complex. It offers direct access to one of the best beaches on the Florida West Coast. This recently remodeled 2-bedroom, 2-bathroom condo offers plenty of amenities. Take the elevator to this 2nd floor unit that provides a partial view of the water from the open balcony. You ca
Hot HOT 39
Playa Encantada 205
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Runaway Bay 212 is a fully furnished 1-bedroom, 1-bathroom condominium in the centrally located Runaway Bay community. The Runaway Bay complex is situated in the middle of Bradenton Beach around many shops and restaurants. Runaway Bay also has private beach access available to its residents and guests as well as a private fishing dock and kayak lau
Hot HOT 28
Runaway Bay 212
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Pool pool
Welcome to Coquina Cottage B! Coquina Cottage B is exceptionally located at the northern end of Anna Maria Island, just steps away from gorgeous Tampa Bay. Enjoy panoramic water views from this three-bedroom, upper level, two story duplex home across from the calm waters and playground amenities of Bayfront Park. Walk to catch the free trolley, sho
Hot HOT 344
Coquina Cottage B
Duplex
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool

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