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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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  • 2nd time here and it is always amazing, pristine clean, smells amazing, right on the beach, friendly staff, great location will return!

    - Rebecca K.

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  • We love staying at Mainsail Beach Inn on Holmes Beach! The Inn is on the beach and has a welcoming and homey atmosphere. We didn’t time on the beach and at the pool area!

    - DEBORAH S.

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  • We all loved the condo including the comfort and location.
    I had condo#1. First floor. It was right in front of the beach and had immediate access. There were 8 of us. We slept very comfortably including The two adults that slept on the pull out couch.
    Concerns were the lack of toilet paper provided and the two showers outside that did not work. The water spouts did keep our feet cleaned.
    And I would most definitely stay here again!

    - Anna R.

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  • The townhome is nearly beachfront (just 15-20 steps away) and the views from the decks & windows are lovely. We appreciated the easy access to beach lounge chairs, bikes & kayaks.
    The townhome worked perfectly for 6 ladies on a girls trip. Having a bathroom off each bedroom was great & the kitchen / dining / living room layout worked well
    too.
    We didn’t have any issues with our stay & would highly recommend this property!

    - Camille A.

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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
866-724-5287

PROUD PARTNER

Homes & Villas by Marriott International

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