bg

Book Your Anna Maria Island Rental In Confidence

Our Top Priority is the Well Being of Our Guests. Click Here to Learn More about our Commitment to Safe Cleaning and our Flexible Cancellation Policy.

Mello

Mello
On the Beach
island dining

Island
Dining
Royal Blue Dreams

Royal Blue Dreams
attractions

Local
Attractions
luxury stays for 7 nights

For luxury stays
less than 7 nights
about us

Book with confidence
Anna Maria Island Rentals

Anna Maria Island
Vacation Rentals
list your property

List Your
Property

Welcome To Mainsail Vacation Rentals

Family-Friendly Anna Maria Island Vacation Rentals

Book a Anna Maria Island beach vacation rental that’s more than just a getaway—make it unforgettable with Mainsail Vacation Rentals. Whether you’re looking to relax in a Holmes Beach condo or to enjoy the coastal charm of Bradenton in a private home, we offer a variety of AMI rentals to suit every family.

Choose from spacious 2-bedroom & 3-bedroom condos located just steps from the sand in the popular Mainsail Beach Inn.

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 AMI 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...



decorative quotation mark
  • After 11 years of renting homes for our Thanksgiving trip to AMI with family we elected to choose a Mainsail Beach Inn condo this year. We were pleasantly surprised with the spacious accommodation and the "bed and Breakfast" feel of the Inn. It was nicely furnished and provided an excellent view of the beach from the south end of Holmes Beach to Bean Point. The on-site management (Property Manager Matthew and his colleagues John and Rhoda) could not have been welcoming and courteous throughout our stay. We shall return!

    - Glenn D.

    stars
  • Our vacation experience was wonderful. We had so much fun despite the cold weather. Unit 11 was clean and worked pefectly for our family. Mathew was incredibly helpful and accomodating when we learned the pool wouldn't be heated during our stay. It's because of his professionalism and kindness of all staff including reservation associates plus the Inn it's self is so exceptionally clean and nice that we can't wait to come back. Thank you for making this trip so special for our family!

    - Dawn T.

    stars
  • Absolutely perfect location on an uncrowded area of Anna Maria Island. Our room on the 3rd floor had stunning 180 degree views of the ocean. The room was beautifully and comfortably appointed. Will visit again.

    - Kyle J.

    stars
  • We WERE repeat customers to Mainsail Beach Inn. They have horrible customer service and are all about the money.The prices keep going up and the service level keeps going down. Our last visit was bad. I spoke to Mainsail before we decided to come during COVID19, that is rampant in Florida. We drove 15 try and relax and what is the first thing we notice on the beach-the huge pipes and renourishment that was going on. Mainsail knew for months that this was going to happen but failed to inform us. I believe they mislead their guests and do not take any responsibility for anything. But, they don't have a problem taking your money when it is due. A decent place would try to rectify the situation but all Mainsail offers to do is offer a small discount on a future visit. We wanted to enjoy the present and be there in the moment but we could not. We could not use the small pool because too many people were in it and COVID is going on. We could not use the paddleboards or kayaks they advertise. We had to drive to a beach so that we didnt have to walk around a huge area of fencing and pipes and very murky water that lay right in front of the Mainsail property. We booked this place because it is beachfront. We drove this far because Anna Maria has the most beautiful clear water. Had we known that any of this was going on then we would have cancelled our trip especially since we risked getting COVID by coming there. There is no excuse for this poor service. It is a beautiful Inn and beautiful beach(when not getting renourished). They use to have a lot of little extra touches to the Inn but I see that budgets cuts have stopped that. The customer service and the outrageous prices are not worth staying at Mainsail. It is sad to see the rapid decline of customer service in this business because I believe we stayed there when they first opened and approximately 7 times.

    - Anonymous

    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
866-724-5287

PROUD PARTNER

Homes & Villas by Marriott International

RESOURCES

Terms & Conditions
Travel Insurance
Area Info
Homeowner Benefits
Owner F.A.Q
Guest F.A.Q
Mainsail Beach Inn
Mello on the Beach
Hunters Point
Waterline Villas & Marina
Rentals A-Z
Diversity
Careers

CONNECT

Sign up for our newsletter for access to our latest specials and updates.
  • This field is for validation purposes and should be left unchanged.

HAVE A QUESTION?
Contact Us
© Copyright 2026 Book with Confidence | Mainsail VR | Privacy Policy | Website Accessibility Policy | Website managed by RealTech Webmasters