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 98 properties available
This pet friendly, ground floor villa is just one block from the beach and a short stroll to shopping and restaurants! Seahorse Villa West sleeps two featuring a king bedroom. Spend your island time in this bright and colorful duplex with free WIFI and washer/dryer.HIGHLIGHTS • 786 sq ft. • Pet friendly • Centrally located near Keyes Marina • 0.3
Hot HOT 18
Seahorse Villa West
Duplex - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
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)
Gulf Watch 204 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 • Waterfron
Hot HOT 12
Gulf Watch 204
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 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 131
Bayside Bliss
Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Pool pool
Rating 5 (5)
Coconut Breeze is a beautifully renovated duplex only a short five-minute walk to the beach. Coconut Breeze is finished in a beach style with tile throughout with custom cabinets & granite counter tops. This 2-bedroom, 2-bath ground level property is just like home, modernly furnished with all the bells & whistles. It sleeps four guests in total. T
Hot HOT 37
Coconut Breeze
Duplex - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Rating 5 (5)
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 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)
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 42
Island Hideaway
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Welcome to Coconut Cottage! This beautiful 3-bedroom, 2-bathroom cottage has 1,620 square feet of elevated living space and the ability to accommodate 6 guests very comfortably inside and out. From the quality quilts and linens on the beds, to the large TV in the living room, the fully equipped kitchen; nothing has been spared when decorating this
Hot HOT 48
Coconut Cottage
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (5)
The Westbay Point and Moorings complex is tucked away on the Bay side of the Island and a very sought-after neighborhood to escape the cold North! Westbay Point 214 is a lovely upstairs, 2-bedroom property with a canal view and with access to a heated pool, hot tub, and tennis/pickelball courts. Enjoy the open floor plan with updated kitchen and a
Hot HOT 40
West Bay Point Moorings 214
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool
Rating 5 (1)
Welcome to Sea Star Villa! This well constructed 3-bedroom, 3-bathroom Island home is ready to host up to six guests comfortably! 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 the
Hot HOT 34
SeaStar Villa
Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Pool pool
Rating 5 (5)
Island Haven is an updated 2-bedroom, 2-bath Island pool home on a canal with a private dock. From the moment you walk in, you will instantly feel relaxed and ready to take on the Island lifestyle. Enjoy this ground level private home in a quiet location. Island Haven has two dining areas and a large open living room with a reading area. There is
Hot HOT 12
Island Haven
Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Pool pool

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