Anna Maria Island Rentals | Book with Confidence | Mainsail VR – Vacation Rentals and Property Management on Anna Maria Island

Take the risk out of your vacation with more control, flexibility, and SAFE cleaning.

Book with confidence on Anna Maria Island

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 accommodations are all near the gorgeous waters of Anna Maria Island. We go above and beyond the competition to bring you the best service and ensure you will love our coastal homes and condos. From one-bedroom suites to 5-bedroom beachfront vacation homes, 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.

Summertime Savings

Promo Code: Summer15

Experience the best of Anna Maria Island from our well-appointed vacation rentals! Save 15% off on stays of 4 nights or more.

Book now through August 31 for stays July 12 through September 30, 2020.

Blackout dates and restrictions apply. Valid for new reservations only.

Things To Do

decorative quotation mark
  • Great property. Only issue was with the lock box. After that was resolved the rest of our experience was fantastic.
    We will do this vacation again.

    - Philip M.

  • Having stayed there Jan and Feb for the past 5 years we obviously like it. We would be there next year as well but Mainstay raised the rental rate by 30% and wants a 50% non refundable deposit. Quin Sabatini was great, very helpful.

    - Anonymous

  • We have stayed here before and have been pleased with the property and location. There were some small maintenance issues that were addressed in a timely fashion.

    - Trey R.

  • very good, left on March 24th instead of March 31st because of theCodiv 19.

    - Marie L.


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


Sign up for our newsletter for access to our latest specials and updates.