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Anna Maria Island Vacation Rentals

from Island Real Estate

Island Real Estate has been serving Anna Maria Island’s vacation rental and real estate needs since 1970. Quite a bit has changed over the last 50 years, but our dedication to our work has remained the same. The recently reinvented vacation rental division of Island Real offers one of a kind vacation rentals and unmatched customer service. Whether you’re looking for beachfront rentals overlooking the Gulf, or a pet friendly rental big enough for the whole family, you’ll find it here at Island Real.

For those looking to make their stay on Anna Maria Island more long-term or permanent, Island Real Estate is here to help. With more than 50 years of real estate experience in Anna Maria City, Holmes Beach, and Bradenton Beach, Island Real is your key to Anna Maria Island. Check out our homes for sale on Anna Maria Island, or browse all MLS listings on the island! From sunning oceanfront mansions to affordable condos, there’s something for every taste and budget here on Anna Maria Island.

Let our team help to find your perfect "peace" of paradise! With the best real estate and property management services since 1970, our qualified team is here to help whether you are looking to rent a vacation rental on Anna Maria Island or purchasing your new Florida home, we are your one stop shop for real estate sales and vacation beach rentals!


family fun

Anna Maria Island Rentals

Rich in old-Florida charm and breathtaking views of the Gulf, Anna Maria Island is a vacation destination second to none. It’s a place where many go to escape the stress of everyday life and enter a world of pure relaxation. With more than 7 miles of soft, sandy beach to explore, and no high rises or highways to distract the senses, you can really get away from it all on Anna Maria Island. Wake up to the sound of waves crashing in your beachfront rental overlooking the Gulf, or bring the whole family and stay in one of our pet friendly rentals.

You're just a few clicks away from booking a relaxing Anna Maria Island Rental for your next vacation! Let our Island Real Estate Vacations team help you find your perfect getaway. Our local team has worked, lived or played on the island for several decades and can help with any questions about the Island including where to stay, where to eat and anything else to help make your vacation perfect in every way! Island Real Estate has managed tens of thousands of visitors to Anna Maria Island, so let our expertise work for you.


dream home


If you're looking to find your own little 'peace' of paradise, you've come to the right place. Since 1970 Island Real Estate has been helping patrons find their get-a-way home, condo, cottage or villa on and off Anna Maria Island. The sales professionals at Island Real Estate are full time specialists, no "weekend warrior" realtors here! With more than 225 years of combined experience working for you, our experts will show you all that Anna Maria Island has to offer. For almost 50 years, Island Real estate has been committed to helping our community through every step of the home buying process. Don't believe us? Just check out reviews of our real estate services.

Anna Maria Island Real Estate

stay in touch with ourLocal Scene BLOG

Keep up to date on the latest happenings on and around Anna Maria Island. What to do, where to eat and all the fun you could possibly have on vacation! Our local vacation and real estate sales experts have created thousands of pages of information on and off Anna Maria Island. The information is shared to make the most out of your vacation or real estate purchase on Anna Maria Island. Check out our top ten lists for Anna Maria Island shopping, restaurants, things to do on rainy days, top burgers, desserts, you name it! Have an interest, we have likely written about it. Use our search functionality or easy informational selections to find out more. We would love to host your next get-away or help with any real estate inquiries you may have. Let Island Real Estate's expertise work for you!