Pets allowed:
Wi-Fi available:

Description from owner

TripAdvisor Property ID: 4880825

About the area

Anna Maria Island is 7 miles long, located just south of the Tampa Bay area and just north of Longboat Keyon the Gulf of Mexico. Beautiful white sugar sand beachesand sunsets that will take your breath away. Parasailing, deep sea fishing charter boats, jet ski rentals, boat rentals, bike rentals, and don't forget to ride the free Island Trolley. Many golf courses within 1/2 hour's drive. The island is full of fantastic restaurants and cafes, many right on the gulf. There are plenty of unique shops including art galleries and antiques. Sarasota if full of cultureabout a 45 minute drive, there is the Ringling Museum, Sarasota Jungle Gardens, the Mote Marine Aquarium (world renowned ocean/science center), and much more. Disney World, Orlando is just about a 2 hour drive. Drive south through beautiful Longboat Key, and you'll reach St. Armand's Circle, on Lido Keyabundant with outdoor cafes, art galleries and quaint boutique shops. A shopping experience you will never forget. Beach, shops, restaurants! BeachHouse Sandbar Gulf Drive Cafe Wicked Taco Bridgetender

Getting around

Free island trolley!

Owner profile

Linda V.
Years listed:

Languages spoken: English



  • Air conditioning
  • Grill
  • Heating
  • Balcony/Terrace
  • Housekeeping Included
  • High Speed Internet
  • Linen provided
  • Private outdoor pool (unheated)
  • Parking Included
  • Pet Friendly


  • Ceiling Fans
  • Clothes dryer
  • DVD player
  • Hair dryer
  • Iron
  • CD player
  • Refrigerator
  • Satellite TV
  • Microwave
  • Stove
  • Telephone
  • Toaster
  • Video player
  • Washing machine


  • Cycling Trips
  • Fishing
  • Water sports
  • Horse riding

Reviews (9)

Very Good – based on 9 reviews Very Good
9 reviews

“Tradewinds Anna maria”

Reviewed 8 Aug 2016

Good location. Clean, well supplied, good daily maid service. Not much area for being pet friendly for bathroom and for walking dog. Parking lot flooded with minimal rain. No overhang on porch at door or over chairs to get out of rain to even enjoy the outdoors. Rain would pour over the edge so no gutter etc., Beaches are beautiful, office staff very user friendly, lots of items provided for beach use. Nice pool and dock. There are multiple amenities provided with this place. I would return and recommend families too.

“Nice Resort”

Reviewed 8 Dec 2014

This was our second stay at Linda's cottage. Great place to vacation within walking distance of beach and local shops. Warm pool and friendly staff. Beach chairs, umbrellas and towels provided. Cottage is so much nicer than one room hotel. Cook in ~ dishes, pans and utensils provided, grill outside, or eat out - restaurants within walking distance or take the trolley. Resort is quiet and grounds are kept up beautifully.

Owner's reply: Thanks Catherine for your nice review! We loved having you stay at our Tradewinds cottage. The Tradewinds on Anna Maria Island is the perfect beach accommodation :) Hope to hear from you again in the future!

“Nice, quiet "old Florida" style cottage”

Reviewed 24 Jan 2014

1 bedroom cottage with kitchen, with spacious closet, flat screen tv and free laundry on property. Next to Bay and across from beach, heated pool. Only amenity lacking was dishwasher.

“A great find”

Reviewed 30 Jul 2013

My wife and I are expecting our first child and we went on our last vacation as a couple only - our babymoon. We couldn't have found a better place to stay. The beach is a very quick walk, the staff was friendly, and the units were well kept. The landscaping and property were immaculately maintained. Just overall a wonderful place that we'll eventually visit again.

“A Piece of Paradise”

Reviewed 4 Apr 2011

We have stayed at the Tradewinds for a week in March for the past four years. The year before that, we were at the Tortuga - a sister hotel. Both properties are kept up extremely well, and we have never been disappointed. This year our visit was interrupted by a violent storm with high winds and torrential rain; however, the day after, the crews were out cleaning up the fallen debris and dealing with the water issue. A great spot to vacation! The only suggestions we have is to get rid of the concrete benches by the pool - they are extremely uncomfortable and are awkward to slide onto. We noticed several elderly people looking for shaded seaing by the pool and with only 3 regular chairs, and the benches, many ended up going back and sitting outside of their room. The concrete tables are great, but please scrap the benches! Also, both the pier railings, and those on the unit facing the bay are starting to look pretty beaten up and require painting. I noticed that one of the sheds was being painted, so hopefully the rest will happen too. Tradewinds is our little piece of paradise - we wouldn't be repeat visitors if we didn't love it.

“Beautiful Vacation Destination”

Reviewed 29 Jul 2010

This was our second stay at the Tradewinds. The cottage we stayed in (35) was perfect. There was plenty of room for my husband and myself and our son. Our daughter and her boyfriend live in Palma Sola so they visited everyday. Even with the 5 of us in the cottage and a yorkie as well, we did not bump into each other. The view from the porch or windows was very nice as we had an ocean view. The front office offered daily beach towels and umbrellas, which was awsome. The location to the beach was good as well. The beaches were beautiful. We enjoyed our stay and look forward to visiting again.

“All that we expected”

Reviewed 12 Apr 2010

My husband and I and another couple recently rented the Gulf Drive Villa at Tradewinds, it was wonderful. The place was nice, clean, in a great location, and was all that we could ask for. The grounds were well kempt, the pool was nice, they came in to clean-up our rental and replenish towels daily (which wasn't the case the few days before when we were in Key West). The location to the beach was perfect, almost right across the street. We thoroughly enjoyed our stay on the island and at Tradewinds resort. We are not picky people, and thought it was wonderful and would recommend it to others and would return ourselves if we return to the island.

“spring break”

Reviewed 5 Apr 2010

Clean rooms, cheerful staff, great location. Pool area clean. Only concern was crossing the busy street to get to beach.


Reviewed 15 Apr 2009

You will fall in love the moment you pull in the drive. We stayed in Unit # 10, and wanted to live their forever. Everyone very nice, guiet, very clean and only steps for the beach, views that post cards are made from. You must try it, and we can't wait to go back. My favorite spot in all of Flordia.

Review 1-9 of 9
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Owner Supplied Testimonials

Our very first customer wrote: "I just wanted to let you know that
we had a great time at your cottage. Our only regret was that we
didn't plan to stay there longer. Anna Maria Island is peaceful and
beautiful, it is one of Florida's best kept secrets. We are hoping
to go back next year and take advantage of some of the things we
didn't have time for. Niki"

We had a fabulous time! Your place was perfect!
It was so nice to be able to walk somewhere nice for dinner,
then take your shoes off and walk home on the beach!
For most of the two weeks we were there, there was "no vacancy" -
but we never had a problem with noise, parking or getting a spot by
the pool. We have memories of Anna Maria Island that will last a
life time! Julie

Hi Linda, our stay at your place was WONDERFUL from the
minute we opened the door. I was very pleased with the
spaciousness, the air conditioning (so comfortable) with the paddle
fans, etc. It was immaculate and there was no lack of supplies.
We enjoyed the dock for coffee in the AM and also evening, with all
the fish activity. We would recommend your place to anyone who
asks. I came home with a beautiful suntan, and some rest which was
so needed. - Mary