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 93 properties available
The beautiful Blue Water Escape! Experience its panoramic rooftop deck views with a location in the heart of Bradenton Beach around the corner from Bridge Street! This three-story duplex features a rooftop deck and balconies on every level. Enjoy celebrating the sunrises over the Bay each morning and sunsets over the Gulf every evening during your
Hot HOT 30
Blue Water Escape
Duplex
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 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 26
Catch N Relax
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
The Terrace 3 invites to a great Island vacation! This beautiful, newly renovated 2-bedroom, 2-bath townhouse style condo sleeps up to five. Traveling couple will enjoy the two queen beds. This resort is located on the west side of Gulf Drive, so there are no busy streets to cross on the short walk to the beach. After a day at the beach relax at th
Hot HOT 19
The Terrace 3
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Pool pool
Rating 5 (5)
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 41
Beach N Bay 206
Duplex - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Pool pool
Rating 5 (6)
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 22
Gladiolus on the Water
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (4)
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 20
The Lady Fish
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
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
Hot HOT 21
Sapphire Beach House
Duplex - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Treat yourself to a great Island getaway in this custom-built ground floor vacation home. AMI Beach Home is just a few steps from the white sandy beaches of Anna Maria Island. It features four spacious bedrooms for up to eight guests and comes with all the bells and whistles needed for a comfortable vacation. HIGHLIGHTS • 2534 sq ft. • Private heat
Hot HOT 57
AMI Beach Home
Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (5)
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
Hot HOT 31
Spring Break
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pool pool
Rating 5 (5)
Welcome to Coccoloba! This beautiful single-family home is located across from the sugar sand beaches in Holmes Beach. You enter the living room that features a large TV for great family entertainment. There is also a small table with chairs for a morning coffee or a cocktail before dinner or just hanging out with a good read. The galley style kitc
Hot HOT 19
Coccoloba
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Welcome to Anna Maria's Dream! This newly remodeled and furnished two-bedroom, two-bathroom vacation duplex is in the heart of Holmes Beach. Guests will enjoy a well-equipped kitchen perfect for preparing a gourmet meal or cook outdoors on the gas grill. The living area is spacious, with plenty of seating for family and friends to take in a movie
Hot HOT 21
Anna Maria's Dream
Duplex
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Luxurious views of the bay and just 285 feet to the white sand beaches of Bradenton Beach. Bay Winds 113 is a 3-bedroom, 3-bathroom townhouse style apartment. This townhouse is very comfortable and extremely well equipped. This property is close to the restaurants and shops of Historic Old Bridge Street and just a minute walk to the beach. There is
Hot HOT 12
Bay Winds 113
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)

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