Duncan Real Estate 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. 


Accommodations For A Perfect Florida Gulf Coast Vacation!

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 brandnew 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 Rentals

Properties Available 92 properties available
Welcome to The Beach House! Amazing Northern end, luxury home sitting on the Gulf of Mexico with a pool! Directly on the Gulf of Mexico, north of Pine Avenue on beautiful Anna Maria Island, The Beach House is a spectacular beach retreat. Looking like an Old Florida beach house on the outside, the interior has been remodeled to make a stunning, comf
Hot HOT 50
The Beach House
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pool pool
Rating 5 (2)
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 32
Flamingo Bay
Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)
Welcome to Catch N Relax! Nestled right amid Anna Maria Island is this 3-bedroom, 2-bath single family home with a private dock. This cottage-styled home offers a spacious floorplan to accommodate six people comfortably. There is plenty of seating in the living area with a decorative fireplace. The second living area at the back of the house featu
Hot HOT 24
Catch N Relax
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Sand N Suds! On the city line of Holmes Beach and the city of Anna Maria and a short walk to the beach, this three-bedroom, three-bathroom cottage home is situated on a spacious corner lot surrounded by lush tropical landscapes for a great deal of privacy. Sand N Suds uses the White Avenue beach access. White Avenue is considered a 'nort
Hot HOT 46
Sand N Suds
Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Pool pool
Rating 5 (3)
Come to this Island home and have a vacation of a lifetime! Totally remodeled, this 3-bedroom, 3-bath pool home is well appointed with designer finishes throughout. The living area has plenty of seating for the whole family. The kitchen is outfitted with gorgeous granite countertops and stainless-steel appliances. Start your day with your favorite
Hot HOT 17
Ebb Tide
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Welcome to Blue Coconut Bungalow! This beautiful, centrally located 3-bedroom, 2.5-bathroom house has 1,612 square feet of elevated living space and offers the best of Island vacationing. Up to six guests will be accommodated very comfortably inside and out. From the quality quilts and linens on the beds, TVs in all the bedrooms and several fantast
Hot HOT 38
Blue Coconut Bungalow
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Located in Bradenton Beach, this fabulous 3-bedroom, 1.5-bath Key West Style cottage with private pool is only a minute to the beautiful Gulf beach. Violetta Cottage is located a short walk from Bridge Street with all its restaurants, great shopping, and the Bradenton Beach City Pier. Violetta Cottage has a large open plan living area with plenty o
Hot HOT 27
Violetta Cottage
Home
Bedrooms 3 bedrooms
Bathrooms 1 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Welcome to Lazy Hammock! This amazing north-end canal front home has everything you need to make this your best Anna Maria Island vacation ever. Park your car in the circular drive, enter through a jasmine pergola to this stunning ground level beach house and never leave! The vacation home is located on the very quiet Hammock Road in the historic c
Hot HOT 19
Lazy Hammock
Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Pool pool
Rating 5 (3)
Welcome to Water’s Edge, a beachfront getaway with stunning views! The Water’s Edge 110N condo is a beautiful two-bedroom, two-bath condo that is located directly on the Gulf of Mexico. This stunning property has undergone major renovations and is embellished with all new appliances, furniture, bedding, art, and much more! Offering picturesque view
Hot HOT 21
Waters Edge 110N
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Rating 5 (6)
Welcome to Beach N Bay 206! A honeymooners delight or a couple’s retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is th
Hot HOT 27
Beach N Bay 206
Duplex - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Pool pool
Rating 5 (6)
Welcome to Conch Cottage! This cottage-style home is part of a triplex in Bradenton Beach on a quiet dead-end street within a short walk to Bridge Street. It is one of the two ground level rental units with the upstairs being used privately. The property sits only five houses from the Gulf Beaches and two houses from the Bay side. This efficiency
Hot HOT 11
Conch Cottage
Duplex - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 5 (6)
Welcome to Island Hideaway! With a prime location on Anna Maria Island, Island Hideaway is perfect for your next relaxing beach getaway. This two-bedroom, two-bathroom condo features updates throughout and has been designed with a vacation in mind. The open floor plan will give you the space to spend time together, while the private bedrooms will o
Hot HOT 66
Island Hideaway
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool

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