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

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luxury stays for 7 nights

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Book with confidence

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

Anna Maria Island beach sunset

AMI History

Anna Maria Island is an experience of history and heritage – Old Florida preserved by the sun for the next generation of visitors. Crystal clear water, miles of white sandy beaches, and genuine relaxation. Where time slows to a crawl...

Fully set table overlooking Anna Maria Island water

Dining with a View

Congratulations on finding a gem of a destination for your vacation! Insulated from everyday worries, Anna Maria Island is celebrated for its world-class beaches, an authentic Old Florida way of life and its eclectic, yet grounded, sense of community. While...

Rain boots and pink umbrella on a rainy day

Rainy Day Magic

While everyone expects clear skies and days filled with sunshine, every now and then the weather might not fully cooperate with your vision of the perfect beach vacation. Don’t fret. We have you covered. While it’s tempting to give you...



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  • 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.

    stars
  • 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

    stars
  • 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.

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

    - Marie L.

    stars

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

CONTACT US

Mainsail Vacation Rentals
5325 Marina Drive,
Holmes Beach, FL 34217
754-465-1164

PROUD PARTNER

Homes & Villas by Marriott International

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