Fall & Winter on Anna Maria Island!

We are delighted that we are now able to welcome guests back to our Pineapplefish rental homes on Anna Maria Island. On May 23, 2020 Manatee County announced that Gov. Ron DeSantis approved the county’s short-term vacation rental reopening plan which was effective immediately and it is so good to be able to see visitors coming back once more, and enjoying our beautiful island.

Of course, like so many, our community businesses have been hit hard, but so many of them are back up and running, and have been working hard to achieve and adhere to necessary and strict COVID-19 guidelines to keep you, and all our community safe. Whether it be open air dining or for drinks, curbside takeout, or delivery. Some of your favorites are open and serving, including: The Sandbar Restaurant, The Waterfront Restaurant, Eat Here, Ugly Grouper, Slims, Scotts Deli, AMI Beach Cafe, The Beach House. And many of our stores are open too: Anna Maria General Store, the new Bait Shop, and Beach Bums, for all your bike rentals, kayaks, paddle boards and more, are amongst those open. So please, we know they  would so very much welcome seeing you, and for your support!

Fall and winter is a really wonderful time to come to Anna Maria Island. While renowned for its peace and tranquility all year round, crowds are at their minimum during the winter months. With such fewer visitors, you’ll have more opportunities to truly experience our authentic Florida culture, get to the know the islanders, and have faster service in restaurants and eateries. And of course, you will have more privacy. You might even get the beach to yourself!

Temperatures are still fabulous and the sun continues to shine. During winter months, average temperatures reach a high of 77 degrees and a low of 65. The waters are warm, both the sea and your rental pool. Although at Pineapplefish, we have solar heating for all our pools, so our temperatures are always perfect! And the humidity is lower during winter months, so the weather really is at its best!

Our weekly rental rates are also much lower at this time of you, and we are able to reduce our minimum nightly stays to 4 nights. So you can even enjoy Anna Maria Island for a relaxing long weekend.

We really do hope that you might consider visiting us this fall or winter. A walk along the shore, a swim in the sea, fishing, relaxing by your pool, or simply unwinding in the peace and tranquality of the island. Whatever you need after the last few months, Anna Maria has it in abundance. We have lots of availability across all our properties, so why not take a look or give us a call and let us help you.

With even more poignancy this year, and with the opportunity to book less than a week in the quieter months, why not take the opportunity to celebrate one of the holiday weekends on the island with your family? Enjoy the beach, each others company, and some time away. We currently have availability remaining for:

Labor Day
Columbus Day
Veterans Day, and
and Christmas

In our homes, whilst our cleaning standard are already exceptional between guests, you can be assured that we are practising all the necessary additional measures to meet and exceed CDC recommendations, and are governed by a mandatory cleaning system as instructed by Manatee County.

We are delighted that people are still coming to Anna Maria, supporting our community and enjoying our beaches. And, with so many now looking for alternative vacations to ones already planned, we will be updating this page regularly with our current availability.

We would love to welcome you back to Pineapplefish and Anna Maria Island! For more information about COVID-19, our standard practices, and safety measures, availability, prices and to book, please get in touch with our team at Sato Real Estate.
Email hello@pineapplefish.com or the office: (941) 778 7200.

Mike Thrasher, Owner
Pineapplefish, LLC


*Under the plan, vacation rental agencies may now accept bookings from residents of U.S. states with an overall COVID-19 Case Rate within the state of less than 700 cases/100K residents as of May 15. Reservations from COVID-19 hot spots identified by the Governor are to be avoided for the next 30-45 days (from May 15). Reservations from international travelers will not be accepted.

Fall & Winter Availability!

From now through until the end of the year, please see our currently availability. This also includes a number of short term stays.


November 5-11: $2,870 (6 nights)
November 15-21: $2,870 (6 nights)
November 28-December 5: $3,350
December 5-12: $3,350
December 12-19: $3,350


October 31-7 November: $3,350
November 15-21: $2,870 (6 nights)
November 28-December 5: $3,350
December 5-12 $3,350
December 12-19: $3,350
December 19-26: $3,850


November 7-14: $2,000
November 14-21: $2,000
December 1-5: $1,143 (4 nights)
December 5-12: $2,000
December 12-19: $2,000


October 31-7 November: $2,950
November 7-14: $2,950
November 14-21: $2,950
December 5-12: $2,950
December 12-19: $2,950


October 31-7 November: $2,800
November 15-21: $2,400 (6 nights)
November 28-December 5: $2,800
December 5-12: $2,800
December 12-19: $2,800


November 7-14: $5,600
November 14-21: $5,320
November 28-December 5: $6,040
December 5-12: $5,320
December 12-19: $5,320

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