Home. Away from Home.
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!
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.
“As soon as you enter the front door you know you’re on vacation, it is beautifully decorated inside and out. If you’re looking for relaxation wait till you see the pool you’ll never want to leave, some days we didn’t”
4 bedrooms, sleeps 8. Private pool. Ocean views.
“This place is amazing with almost total privacy yet right on the beach. Beautifully decorated, immaculately clean. A great pool. You won’t be disappointed”
Gulf side. Beach front. 3 bed. Sleeps 8. Secluded private pool.
Beautifully decorated and landscaped with every amenity imaginable provided. Its location was ideal with the blue gulf waters and beach across the street and restaurants within walking or biking distance. Lemonfish is a property I would want to return to or more accurately say never want to leave”
4 bedrooms. Canal front. Private pool. Great location
“The villa itself was prefect accommodation, very colorful and well decorated. The favorite part for us all was the balcony with the lovely views across the Bayou, which had a huge table and chairs and this is where we spent most of our time”
Waterfront. Private dock. Dip pool. Beautiful screened porch
“Once we unpacked, we simply didn’t want to leave for anything: groceries, restaurants, or beach–although all of that is so close by and wonderful! Mintfish is just what we were hoping for: spectacular pool, the floorplan open and airy, rooms colorful and updated, all on one level, room to spread out, large bedrooms and a great view! “
Panoramic views of Bimini Bay. 4 bedrooms. Private pool.
“We loved staying at Honeyfish. It DID have stunning and amazing views across the Bay just like they described. We loved watching the moonlight on the bay, as well as seeing dolphins, manatees, ducks, and other wildlife swim right in front of us as we sat on the back deck. I would highly recommend it!”
Bimini Bay Waterfront. Secluded pool. 4 bedrooms. Sleeps 10
Explore Anna Maria Island
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.
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