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Welcome to Anna Maria Island!

With award winning white sand beaches, crystal clear blue waters, old Florida charm, and year round sunshine, Anna Maria Island is one of Florida’s most stunning destinations on the Gulf Coast. Join us, take a look around, discover our homes and come dip your toes in the water!

Wonderfully Unique

We pride ourselves on the fact that guests come back and stay with us year after year. You will not find anything else quite like Pineapplefish on Anna Maria. Gorgeous beach front and waterfront homes, close to all the boutique stores and finest dining, Pineapplefish offer a unique and perfectly located island experience, with spectacular views, private pools, beautiful decor and family comfort. Come take a look around, and discover your perfect Pineapplefish Home.

Our Homes

Explore Anna Maria Island

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Let us show you round

Come and take a look around Anna Maria. Find where each of our Pineapplefish homes are on the island and in location to some of our favorite and highly recommended restaurants, and eateries, bars and boutique stores.

As well as our stunning island history, historic Piers and buildings, our museum, mhurches, and of course our award winning, white sandy beaches, there are many of wonderful things to discover and enjoy on Anna Maria Island.

Come immerse youself in the tranquil and laid back culture of our Old Florida style.

Come Explore

Bikes & Buggys


A birds eye view

of the beautiful Anna Maria Island


Take to the water

and enjoy a catamaran trip


Things to do on

Anna Maria Island



Anna Maria Island