Anna Maria Island Accommodation

    A little bit about Pineapplefish

    Welcome to Pineapplefish Villas, our unique vacation rentals on Anna Maria Island.  We are delighted that you have taken the time to view our Anna Maria holiday homes and hope that you will love what you see.


    At Pineapplefish we have eight villas available to rent, all of which have been personally designed by us with their own characteristics and features that make them truly unique! Watch our individual property videos on the pages below, giving you a unique insight into each villa. 
    Our properties boast beautiful locations; from spectacular waterfront views to direct beach access – our villas have it covered!
    We are pleased to have created villas that can cater for every need, from newly-weds intimacy to family fun to large group amenities. Take a look at each individual holiday home to appreciate what they have to offer. You can also compare all of our villas to pick your own piece of paradise!


    • Beach Front
    • 3 Bed / 4 Bath
    • Sleeps 8-10
    • Private Pool
    Limefish enjoys one of the most enviable beach front locations on Anna Maria. Rated "amazing" "a gem" and "the perfect setting" on Tripadvisor. Read more reviews.


    • Gulf Front
    • 3 Bed / 2.5 Bath
    • Sleeps 6
    • Private Pool
    Fall in love with Yellowfish, one of the most impressive and luxurious homes on Anna Maria Island, located directly on the Gulf front, on exclusive North Shore Drive.


    • Waterfront
    • 4 Bed / 4 Bath
    • Sleeps 10
    • Private Pool
    A block from Tampa Bay Beach, Mintfish is a spectacular home on the edge of Bimini Bay in Anna Maria.  A beautiful, spacious, 4 bed rental with stunning views.


    • Water Front
    • 4 Bed / 4 Bath
    • Sleeps 8-10
    • Private Pool
    Watch dolphins & enjoy spectacular views across Bimini Bay. A fantastic waters-edge location, Honeyfish is a spacious, stylish, 4 double bed rental with private pool.


    • Tampa Bay Beach
    • 4 Bed / 3 Bath
    • Sleeps 8
    • Private Pool
    A short stroll to Tampa Bay Beach, an abundance of lavish fixtures & high quality décor, 4 beds & a fantastic private pool area. Find out more about Cherryfish villa.


    • Canal Front
    • 4 Bed / 3.5 Bath
    • Sleeps 8-10
    • Private Pool
    Lemonfish is a fabulous & spacious Key West style canal front, 4 bed villa, close to City Pier.  Perfect for larger family group vacations on Anna Maria Island.


    • Waterfront
    • 3 Bed / 2 Bath
    • Sleeps 8
    • Private Pool
    Plumfish is a beautiful Old-Floridian style home, overlooking the Hammock Bayou on Anna Maria Island. Bright, 3 bed rental with private pool.


    • Gulf Beach
    • 6 Bed / 4 Bath
    • Sleeps 6-12
    • Private Pool
    These 2 Caribbean style apartments are perfect for larger groups vacationing together on Anna Maria. Shared deck and outside pool, with stunning Gulf views. 6 beds.
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