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

Where to Enjoy Anna Maria Island Waterfront Dining

One of the best parts of a beach vacation is enjoying a meal with a view of the water. Anna Maria Island offers several restaurants where guests can watch boats pass by, listen to the waves, or catch a colorful...

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
  • We had an overall great vacation experience. About two hours before check-in I received a call that the air conditioner had went out in the unit I had rented and they would need to re-arrange our stay a little. They made accommodations for us at Waterline Marina Resort and the resort was fabulous, however, it was not directly on the beach but we were assured an available unit at Mainsail the following day, so we were just displaced one night. The only drawback was that the original unit I had rented was ocean view (I love to sit on balcony and look at ocean), but the first floor unit we ended up with was not. Ending up on the first floor didn't hamper our stay. We were just a few short steps from our unit to the sand. Would definitely stay again!!

    - Anonymous

    stars
  • We had condo #10 at Mainsail, and it was very clean and neat. Very comfortable beds, and not too bad of a view, because when we opened the front door, we could see the ocean. Loved staying at Mainsail for the second time. Will use them again!

    - Cynthia J.

    stars
  • We arrived and instantly felt relaxed! The staff was so incredible; they went the extra mile! Having lounge chairs, SUPs and bikes available added to our experience. We would go back in a heartbeat!!

    - Jeffrey W.

    stars
  • 4th or 5th year we've come. Had a great time with three generations of the family. Thank you for a very relaxing vacation.

    - David Q.

    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