Book With Confidence on Anna Maria Island and Sarasota, 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.

For luxury stays
less than 7 nights

Anna Maria Island
Vacation Rentals

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. We also offer Holmes Beach rentals from 1-bedroom suites to 3-bedroom condos.

Our inventory also includes a beautiful house rental in Sarasota, Florida, fully equipped with a family friendly pool, outdoor grilling area, and a furnished laundry room. Book online with confidence today.

What are you waiting for? Book your rental today! By reserving your stay on our website, we guarantee you the best rate.

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Absolutely fabulous. John, Rhoda and Matthew all 5 stars
- Cheri R.
My family enjoyed an amazing time in Unit 11. The townhouse was extremely cozy, well stocked, and immaculately clean, while being nicely maintained. The friendly management, Matthew, John, and Rhoda, made us feel so welcome, and were always available for questions. The beach, pool, and hot tub were only steps away. We also found the balconies great areas to gather outdoors. We could not have stayed at a nicer resort!
- Anita W.
Have stayed in much better places for far less money (including on AMI). Did not expect the layers of dust, broken window latch, etc.
- Anonymous
This was a trip that my wife had dreamed of taking. She had fond memories of Anna Maria Island from her childhood. She was a little concerned that it may not be all that she remembered; however, it was more than we expected. The beach, sunsets, food and lodging made a great trip for our family. The service and hospitality at Mailsail went beyond expectations. The staff was extremely kind and helpful.
- James S.

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Property Management

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

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Book With Confidence on Anna Maria Island and Sarasota, 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.

Mello
On the Beach

Island
Dining

SAFE cleaning

Local
Attractions

For luxury stays
less than 7 nights