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
So Beachy Chic is a gorgeous newly remodeled 2-bedroom, 2-bath Island pool home with a private dock located in Holmes Beach. From the moment you walk in, you will instantly feel relaxed and ready to take on the Island lifestyle. The white sand beaches of Anna Maria Island are a short three block walk from this home. Or take a leisurely bike ride to
Hot HOT 26
So Beachy Chic
Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
The Palm Leaf is a newly remodeled three-bedroom, two-bathroom private home with a pool and spa. This fabulous house is only a short walk to the white sand beaches of Anna Maria and a short walk to Bayfront Park. Stroll down to Pine Avenue and dine out at one of the many fine restaurants. Don't forget to explore the island on the free trolley that
Hot HOT 32
The Palm Leaf
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)
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 7th Heaven on beautiful Longboat Key! A beachfront escape directly on the Gulf of Mexico with views of turquoise waters from your balcony. Plenty of amenities to enjoy a quiet dinner at the condo or eat out at one of the many Long Boat restaurants. Explore John Durante Park which is right across from the Sea Club Condo Complex. The one
Hot HOT 29
7th Heaven
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Pool pool
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
Bay Winds 113
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)
This pet friendly, ground floor villa is just one block from the beach and a short stroll to shopping and restaurants! Seahorse Villa East sleeps four in total with a king bedroom and a sofa sleeper. A full kitchen, free WIFI and washer/dryer are provided. HIGHLIGHTS • 786 sq ft. • Pet friendly • Centrally located near Keyes Marina • 0.3 miles fro
Hot HOT 17
Seahorse Villa East
Duplex - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
Talk about location! Wrights Retreat is barely a block away from the sugar white sandy beaches on the Gulf of Mexico. This spacious three-bedroom cottage-style home is located West of Gulf Drive in Holmes Beach and can host up to six guests. It features a comfortable and spacious family room, master bedroom with an ensuite bathroom and two guest be
Hot HOT 20
Wrights Retreat
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Emerald Surf is a newly remodeled three-bedroom, two-bathroom canal front home with a pool in the city of Anna Maria. This fabulous house is only 2 short blocks to the white sand beaches of Anna Maria Island and a short walk to the restaurants and shops on Pine Avenue. The easy ground level living offers a large living room with plush seating for t
Hot HOT 32
Emerald Surf
Home
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Rating 5 (4)
Professional Pictures coming soon!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 super
Hot HOT 32
The Getaway
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool
Welcome to Coquina Cottage! Relax stress-free in this two-bedroom ground level duplex accommodation with water views, across from Bay Front Park and within walking distance of Bean Point, gulf beaches, restaurants, bars, and shopping on Pine Avenue. Coquina Cottage is on the north-end of the Island in the City of Anna Maria. Enjoy the views of the
Hot HOT 19
Coquina Cottage A
Duplex
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (4)
Welcome to Gulf Sands, a beachfront getaway with stunning views! Gulf Sands 108 condo is a beautiful two-bedroom, two-bath condo that is located directly on the Gulf of Mexico. Offering picturesque views of the white sugar sand and turquoise water, a shared heated pool and an open balcony overlooking the beach! Simply sit back, relax, and enjoy the
Hot HOT 35
Gulf Sands 108
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Pool pool

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