March and April, are the most popular times on Anna Maria Island, and we welcome back guests year after year at this time. If you are looking for your dream vacation for 2018, we would love to welcome you to beautiful Anna Maria, and our Pineapplefish homes. But as with everywhere across the island, availability is limited. We have just a few last remaining weeks for all of March and April, so hurry and reserve your Pineapplefish rental for as little as $500!


  • 17th March: $4,500
  • 28th April: $3,750


  • 17th March: $4,080
  • 7th April: $4,080
  • 14th April: $3,400


  • 17th March: $3,900


  • 3rd March: $2,250
  • 7th April: $2,700

We also are delighted to offer a few, short break deals:


  • 29th April-4th May: 5 night stay. Special offer rental rate: $2,500


  • 21st-25th April: 4 night stay. Special offer rental rate: $1,800


  • 15th-17th February. 2 night stay. Special offer rental rate: $800


  • 15th-17th February. 2 night stay. Special offer rental rate: $600

All prices above are weekly rental rates. All other fees, including cleaning, administration and taxes (12%) apply. For full information, and prices, please contact our team at, or telephone (941) 778 7200.

We, Pineapplefish Unique Island Rentals, offer a collection of the most exclusive properties in some of the most pre-eminent waterfront locations found anywhere on the island. All 6 homes have been individually and professionally designed, bringing attention to key features of the style of home and their beach or bay front location. Private towers with 360 views or picture windows looking out to spectacular views. Expansive decking and stunning outside space to enjoy, with plenty of loungers, dining tables and BBQ’s. And gorgeous secluded swimming pools set in beautifully landscaped gardens, making the most of their beautiful vistas and showcasing the lifestyle of Floridan, outdoor living.

Inside, discover, open plan living, spaciousness, beautiful and original decor, sumptuous furniture, and little soft furnishings and extra touches, make each Pineapplefish property, a home from home, completely unique from each other and from anything else you will find on the island.