Book With Confidence on Florida's Gulf Coast

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.

For luxury stays
less than 7 nights

Anna Maria Island
Vacation Rentals

Welcome To Mainsail Vacation Rentals

A Florida Gulf Coast Vacation Awaits

Discover the pristine and unique stretch of beaches with a Anna Maria Island rental nestled along the picturesque Florida Gulf Coast. Our selection of accommodations ensures proximity to the renowned turquoise waters of AMI, offering an unparalleled experience in coastal living. With elevating standards, we prioritize exceptional service to ensure your complete satisfaction with our Florida Gulf Coast Rentals. Explore our diverse offerings, ranging from 2-bedroom, 3-bedroom, or 4-bedroom condos located in beautiful Holmes Beach.

Additionally, indulge in a luxurious 2-bedroom house rental in Sarasota or a 3-bedroom house in Bradenton, Florida. Each featuring a range of amenities including a family-friendly pool, outdoor grilling area, a private boat dock, and a fully furnished laundry room. Embrace the allure of Gulf Coast living and reserve your perfect retreat with confidence through our convenient online booking platform.

Why wait any longer? Secure your dream rental today and unlock the best rates guaranteed when you book directly through our website.

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Our rental had a spectacular view of the gulf! You can’t beat it. Fabulous location and steps from the ocean. We loved the huge sliding doors and kept them open. The beds were really comfortable and it was clean and nice. The kitchen was nicely organized. Also, it was great to have use of bikes, paddle boards, and kayaks and the front desk crew is really great. The only criticism is that the sofa and chairs are extremely uncomfortable. It’s hard to believe. Our friends had warned us of that, I think they need be changed.
- Anonymous
We’ve read a lot about Anna Maria Island and knew we needed to explore it. The island didn’t disappoint! Great sunsets, bike riding, meals and close enough to do day trips. The Mailsail property is in a great location and really nice beach access and sports activities as complimentary. The only miss we found was items in the kitchen, e.g. spices and cleaning supplies.
- Mike S.
This was our first trip to AMI and Mainsail. What a pleasant surprise! We met up with family from Nashville and had the best time. Mainsail was perfect! Our main goal was to find a spot on the Gulf that was away from high rise condos, fast food, and other chain stores. AMI was wonderful and had EVERYTHING we needed. Access to chairs, kayaks, paddle boards, grill, and pool was so nice - and not having to get nickel and dimed for every amenity. Mary was a wonderful host and was so responsive to the couple request we had. Thank you for such a nice experience. Can’t wait to go back!
- Anonymous
We had a wonderful stay! All of the staff were friendly and helpful:) The property was spotless and beautiful... we loved it and hope to come back soon♥️
- Paul B.

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Book With Confidence on Florida's Gulf Coast

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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On the Beach

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For luxury stays
less than 7 nights