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Anna Maria Island Vacation Rentals

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Vacation Rentals on Anna Maria Island

We are the Flip-Flop Company. The Anna Maria Island Accommodations team exudes the laid-back Island vibe. With many years of Anna Maria Island vacation rental property management under our belts, we are resident experts and are always ready to share our vast wisdom of all things AMI. We invite you to relax and enjoy an extraordinary vacation experience. So lose the shoes and live life like a local in one of our many amazingly appointed Island vacation homes.

Three Cities, One Island

Welcome to Florida’s most charming beach town. With its clear turquoise waters, white powdery sand beaches, and spectacular sunsets, Anna Maria Island is a rare gem. From the moment you step foot, you will experience an "Old Florida" feel entwined with an easy-going ambience. Whether you choose to rent a vacation home in Anna Maria, Holmes Beach, or Bradenton Beach you are sure to be captivated by the Island’s allure.

OUR NEWEST PROPERTIES

Shimmer

4 Bedrooms

4 Baths

8 Guests

Bikinis And Martinis

4 Bedrooms

4.5 Baths

8 Guests

Key Largo Cottage

3 Bedrooms

3 Baths

6 Guests

What Our Guests Are Saying

We have rented from AMIA four times and keep returning to them year after year. The level of customer service is amazing, the rental process is very organized and they keep in touch via email. Any time we have had a minor maintenance concern or question, they have been able to answer or resolve the issue quickly and easily.

- Susan Porter

We loved working with AMI Accommodations! They matched us with a PERFECT place for a vacation on AMI! Ideal location, close to the gorgeous beach and downtown Pine Avenue. Our family of four had plenty of room to eat, sleep and relax in this immaculate home. Layout was fantastic! Super fun basement with shuffleboard opened

- Virginia Russo

We loved our rental house and our time on Anna Maria Island. Working with Anna Maria Island Accommodations was seamless. Our unit was spotless and exactly as presented online. Everyone we communicated with was friendly and helpful. I would definitely book through them again.

- Kelli Tenbrock

AMI Accommodations was the best rental company I've ever dealt with. Their pre-arrival and departure communications were superior. And the few minor maintenance issues we had during our stay were handled with courtesy and "whiplash" speed! What a great group of folks they have on staff.

- Leigh Farmer

The staff of Anna Maria Accommodations were courteous, friendly and professional. I had to have maintenance for minor issues at our rental. Our issues were addressed promptly and efficiently.

Frances Bonin

This house was nothing short of amazing! Perfect location and was immaculate! AMI Accommodations was so on top of everything the entire week we were there. If we had even simple question they were there to take the call. We all cannot wait to come back!

- Miss Charlie

We have used Anna Maria Island Accommodations for about nine years now. All our experiences have been positive beyond expectations. The cottages we have rented are clean and well equipped. The beds are comfortable and the spaces are welcoming. The best part of this enterprise is the people they employ.

- Susana Isaacson

AMIA is the best vacation rental service on Anna Maria Island. My husband and I have been renting from them for years. The people at AMIA are knowledgeable about all things Anna Maria, friendly, helpful, and efficient, and accommodating.

- Denise