Now Featuring Exclusive Four Bedroom Homes on Islamorada!

Book with Confidence on Anna Maria Island, Sarasota and Islamorada, FL

Our Top Priority: The Well Being of Our Guests and Associates. Learn more about our COVID-19 response and commitment, including SAFE cleaning and our flexible cancellation policy.

Welcome To Mainsail Vacation Rentals

Our Anna Maria Island accommodations are all near the gorgeous famous turquoise blue waters of AMI. We go above and beyond the competition to bring you the best service and ensure you will love our Anna Maria Island rentals. From one-bedroom suites to 3-bedroom Anna Maria Island beachfront vacation rentals, we have a rental that will fit your needs. What are you waiting for? Book your rental today! By reserving your stay on our website, we guarantee you the best rate.

Things To Do

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  • Our experience at Mainsail was unbeatable. The townhouse was immaculate and decorated so well. The mattresses in all 3 rooms were very comfortable. Everything was provided even umbrellas for the beach. The pool/hot tub were steps from our door. And the ocean was 50 steps away. The staff were kind and treated our children well. We will stay here again, no doubt.

    - Anonymous

  • Can't beat the view and relaxed atmosphere. Come and go as you please yet the staff is always ready to assist.

    - Lars A.

  • our experience was overall spectacular. the view is breathtaking. the staff is very friendly and helpful. we did have a few issues, our dryer did not work, the hot tub heater was broke, as well as tile around the pool with orange cones during our entire stay. the balconies are so narrow you can not pass by chairs. but these things did not take away from our overall visit and I would stay here again.

    - Kristina C.

  • Great location right on the beach. The advertised chair service was misleading - they unlock the chairs and you have to then drag to/from their spot in the beach. That was not how I had interpreted from the website. Good size pool (and clean) when you want a break from the beach. Our unit was well worn more than the pictures showed online but everything worked fine. The sunset views right from our balcony more than made up for it! Management did super job cleaning the common areas to remove sand. Added plus having free access to paddleboards and kayaks. Overall, a solid good stay.

    - Anonymous


Property Management

Our fantastic marketing and direct booking process means you can spend less time worrying, and more time relaxing.

See How Easy It Can Be!
AMI Chamber of Commerce


Mainsail Vacation Rentals
5325 Marina Drive,
Holmes Beach, FL 34217


Homes & Villas by Marriott International


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