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)
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 16
Latitude Adjustment
Duplex - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
Welcome to Coral Beach! 4-Bedroom Renovation in Progress! This beautiful 3-bedroom, 2-bathroom pool home comfortably accommodates six guests. From the quality quilts and linens on the beds, to the TVs in the two living rooms and the fully equipped kitchen, nothing has been spared when decorating this home. You will not want for anything when it com
Hot HOT 37
Coral Beach
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Fun N Sun is a second-floor unit in the Runaway Bay community. Enjoy the sights and sounds of this tropical getaway and all the amenities of the Runaway Bay Complex being a shared heated pool, private beach access, a club house with a kitchen and living areas to relax and unwind, also a tennis court, shuffleboard, bocce ball, pickleball, fitness ce
Hot HOT 20
Fun N Sun
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Pool pool
Rating 5 (1)
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
Hot HOT 20
Cayman 201
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Rating 5 (4)
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 28
Lazy Hammock
Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Pool pool
Rating 5 (3)
Welcome to Sea Pirate 5! Across from the beach access on Anna Maria Island. Sea Pirate 5 is a beautiful two bedroom, one bath villa that is located directly across from the amazing beaches of Anna Maria Island and the Gulf of Mexico. Sea Pirate is a private 8 villa complex with a large shared heated pool. An open private court yard to enjoy al fr
Hot HOT 41
Sea Pirate 5
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Pool pool
Gulf Watch 112 is a completely updated 2-bedroom 2-bathroom gulf to bay condo located in the Gulf Watch condo community. Gulf Watch is a beautifully maintained complex boasting a sparkling heated pool all-year round. This condo is located in Bradenton Beach and is only a few steps away from the beach, shopping, and dining. HIGHLIGHTS • Waterfront
Hot HOT 26
Gulf Watch 112
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (4)
Welcome to 1 Step Closer! This beautifully renovated duplex is only a short five-minute walk to the beach. 1 Step Closer is finished in a beach style with hardwood flooring throughout with custom cabinets & granite counter tops. This two-bedroom, two-bath elevated property is just like home, modernly furnished with all the bells & whistles. It slee
Hot HOT 32
1 Step Closer
Duplex
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 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 30
Spring Break
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pool pool
Rating 5 (5)
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 18
Flamingo Bay
Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)
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 36
Runaway Bay 212
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Pool pool

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