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Anna Maria Island Rentals

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Welcome To Mainsail Vacation Rentals

A Family-Friendly Beach Vacation Awaits

Take a beach vacation that’s more than just a getaway—make it unforgettable with Mainsail Vacation Rentals. Whether you’re looking to relax on Holmes Beach or enjoy the coastal charm of Bradenton, we offer a variety of Anna Maria Island vacation rentals to suit your family’s needs.

Choose from spacious 2-bedroom & 3-bedroom condos located just steps from the sand. Spread out and relax in our Holmes Beach house rental featuring a private pool.

Looking for something on the water? Our Bradenton beach house rental includes three bedrooms, a private dock, and a pool.

At Mainsail Vacation Rentals, you won’t have to compromise. Enjoy premium accommodations without stretching your budget.

From miles of white sandy beaches to stunning Gulf views, vibrant shopping, dining, and family-friendly attractions—there are plenty of things to do on Anna Maria Island. Start your vacation today with Mainsail Vacation Rentals.

Things To Do

Anna Maria Island

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...

people eating at anna maria island restaurant

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...

anna maria island pier

Guide to Anna Maria Island Piers

Anna Maria Island is a quaint, yet vibrant vacation destination, providing the perfect balance between relaxation and activity. You can spend your days lounging on the white sand beaches, chatting with the locals at a coffee shop, or strolling through...



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  • The property is clean and the location is great! The cabinets are a bit worn in the kitchen - but we were there for the beach and relaxation - so we didn't mind. The beds were really comfortable and the townhouse was very clean. The staff at the office were helpful and very accommodating! We needed a few additional coffee mugs and an extra parting space for our golf cart for a night and it was no problem at all. I would definitely go back to Mainsail !

    - Jean S.

    stars
  • I have visited Anna Maria Island several times but never stayed in Holmes Beach, always in Bradenton Beach. In fact Mainsail was not my first choice but I was absolutely delighted when getting there that although my vacation in October 2022 was booked in November 2021 my original choice was already booked. (As I live in the UK I have not been able to visit for quite a while and had to cancel a reservation for a resort nearby because of covid). We fell in love with Mainsail immediately.

    Mainsail is beautiful, the apartment is gorgeous and there is absolutely every amenity that you could possibly want. I have been to many places in the U.S staying in top rated hotels and nothing could beat what was ready and waiting at Mainsail. We arrived late in the evening and so in the morning when we opened the curtains the view just took our breath away. We never got over simply looking out to sea and as we live very close to the coast that says something for our third floor apartment in Holmes Beach. The staff there could not do enough to help in any way possible but are also lovely and friendly as opposed to treating it as 'just a job'. We love the whole area and always visit Longboat Key, St Armands Circle and have, even in the past, Casey Key but Mainsail is a wonderful place to base all our future trips - so peaceful.

    Finally - we will definitely stay again, hopefully in exactly the same apartment.

    - Joan R.

    stars
  • Hello, I am a Property Manager as well, so I know the drill. Matt and Rhoda were fantastic . When ther was an issue not only did they resolve it. They followed up as well. I have stayed there four 5 yrs, seen a few managers. Matt is bu far the best . I think the bike system they have needs to change so we rent our own . The property is beautiful , peaceful and extremely clean and comfortable . Already booking for next yr. Island is easy to navigate with fantastic beaches. Best place and staff ever. GO!

    - Melinda M.

    stars
  • We loved the Mainsail! Large rooms, great kitchen, amazing view and location. Super clean! Will definitely be back!

    - Anonymous

    stars

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Mainsail Vacation Rentals
5325 Marina Drive,
Holmes Beach, FL 34217
866-724-5287

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