Gulf Coast Island-Tradewinds Resort Cottage Rental

Tradewinds CottageTradewinds CottagePool on Sarasota BayLiving room/open kitchenKitchen-breakfast bar/dining areaLiving room areaEntrywayBedroomBedroom/walk in closetBathroomFishing DockFishing DockPicnic area/charcoal grillsResort EntrywayBeach!Beach Fun!more beach!powdery sand...Dolphin sighting!Sunsets!Sunsetsand more sunsets!!!
“ Excellent ”
14 Reviews
1603 Gulf Dr N, Anna Maria Island, FL 34217



Bedrooms: 1
Bathrooms: 1
Sleeps 4
Per night $155 - $265
Per week $851 - $1,364
Type: Cottage
Description of the Anna Maria Island vacation cottage rental
Welcome to Paradise

4th night is free with any day check in through Feb 14, 2015!!!
Holidays excluded from free night deal...
Note, Most dates for this upcoming "high" season are very booked up!

This property is within a small resort, just steps from a beautiful private gulf beach on Anna Maria Island in Bradenton Beach, Florida If you want "clean and quiet", you've come to the right place

Condo Cottage with Old Florida Charm This island cottage is: 1 bedroom with king bed (or 2 twins, upon request) 1 bath, full kitchen with open floor plan and breakfast bar, living room w/sofa sleeper, DVD, VCR and cable TV (2 flat screen). Unit sleeps up to 4 people.
533 sq.ft.inside, 662 sq.ft. including the outdoor porch. Everything you need is here! Fully equipped...! Resort has a heated pool on the Sarasota Bay, on-site laundry facility, free WI-FI, and fishing dock. Daily housekeeping service is provided, fresh towels, etc. There is a private barbecue grill and picnic area. The front desk will provide beach towels, beach umbrellas and free video library. (this is a smoke free unit)
TV's have been upgraded to flat screens... living room and bedroom.

Ours is north unit #10. Please visit Tradewinds-Resort link and click on the virtual tour link. There you will see the resort layout. The island is very narrow here, and this overview shows the gulf and the Sarasota Bay, with a complete drawing of the resort, the pool and cottages locations. This is very helpful.

I help other owners get bookings at our resort (and others!)... if our unit is occupied, I can still help you! Please contact me! Thank You!
I have access to all units!!! Even other properties!


Linda Virgils

Area Info
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.


Property Rates

Begins Ends Week
Weekly Monthly Min
Aug 01 2015 Feb 14 2016 $155 $180 $851 - 1 Night
Jan 25 2016 Feb 14 2016 $155 $180 $851 - 1 Night
Feb 15 2016 Apr 06 2016 $235 $265 $1,364 - 1 Night
Apr 07 2016 Jul 31 2016 $220 $245 $1,272 - 1 Night
: 4 p.m. : 11 a.m.
Lodging tax: 11.5%
Deposits: For less than 1 week's stay - 2 night deposit For 1 week or longer, 50% deposit required. 4th night is free with check-in any day now through 2/14/2015 4th night is free starting April 7 through July 31 with a Sun or Mon check-in. 4th night is free starting Aug 1 through Feb 14, 2016 with check-in any day.
Payment Options: American Express, Discover, Mastercard, Personal Check, Visa
Other Fees: All money is paid directly to the resort... to make a reservation.. I will call the resort for you (please do not call and make your own reservation). I need your name, exact dates, the number of people staying, and a phone number. Weekly special prices do NOT include daily housekeeping - There will be a one time departure clean fee for the weekly special price. Holidays may have a slight sur-charge and free nights do not apply during holiday Pets $50 each - limit 2, must be under 75 lbs


Reviews for this vacation cottage rental in Anna Maria Island, Florida

George Lasater

George Lasater

Leawood Kansas

Anna Maria island resort

March 25, 2015

We did not stay there. We stayed at Anna Maria island resort. It was dated and not kept up well. The back slider would not lock. The black out curtains or drapes that where supposed to be on the living room windows were not present, the hard wear for them was. The room would have been much too light because of all the lighting outside to sleep in. The blinds on these windows were slightly broken and left gaps. The back deck was filthy with no brooms or cleaning supplies with which to clean it. The bed was horrible, extremely lumpy and amazingly soft and uneven. Felt much like sleeping on a huge bed of fresh marshmallows. It was otherwise clean and functional and everyone seemed quite nice. Judith James

Barbara McMahan

Barbara McMahan



March 10, 2015

?????i Did Not Use This Property????

Jo Ann Gornet

Jo Ann Gornet


Quaint Cottage on the Bay

March 8, 2015

If you want to feel like you have gone back to the way Florida used to be Tradewinds Resort on Anna Maria Island is the place for you. Our cottage, #21, was roomy and clean. The location overlooking the bay was incredible and it was a very quick walk to the beach. Overall our stay was delightful and the following are suggestions to make it even better. My husband and I have rented vacation properties from coast to coast and in Hawaii so we are not new vacation renters. I immediately had to go out to purchase hangers so that clothing brought for our two week stay could be hung up. No pantry items were provided. In all of our previous rentals basic pantry items like salt, pepper, sugar, and many things left by previous guests are stocked in the cabinets as well as a few things like mustard, catsup, relish, etc. are always in the fridge. Our rule is to not shop until we check things out. We were very surprised to find none of the basics. The pots and pans were sparse to say the least and not a single baking pan or casserole dish was to be found. No electrical appliances except a coffee maker and microwave. Baking my husband"s birthday cake was not possible. The side of the fridge was covered in rust and the stove left a lot to be desired. We did enjoy our time on Anna Maria but didn't feel the amenities at Tradwwinds Resort justified the amount charged for a two week stay. If you need a resort that is pet friendly this is the place for you but I'm not sure I would return unless some updates are made.

dennis varbaria

dennis varbaria

new jersey


January 20, 2015

want a 2 week rental in may 2015

Catherine Myers

Catherine Myers

Fingers Lakes, New York

Nice Resort

December 8, 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!

Sharon` Nordic

Sharon` Nordic

Fort Collins, CO

Wonderful property!

February 1, 2014

One of the most delightful places we have ever stayed at! Weather was horrific but it was a great place to be to stay out of the rain and wind! Would stay here again!

Dorothy J Chambers

Dorothy J Chambers

Louisville KY

Nice, quiet "old Florida" style cottage

January 24, 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.

Owner's reply:

Thanks for your review Dorothy! Glad you enjoyed your stay and hope to hear from you in the future!

Mike Zito

Mike Zito

West Palm Beach

A great find

July 30, 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.

Sue Scott

Sue Scott

Ontario, Canada

A Piece of Paradise

April 4, 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

July 29, 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.



Milwaukee, WI

All that we expected

April 12, 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.

Christine Clay

Christine Clay

Lexington Ky

spring break

April 5, 2010

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



Derry, NH USA

Quite get away

December 5, 2009

We enjoyed our stay it was very clean and nice and quite. It was in a great location and the beach was just a few minutes away. Would book again in the future.....Wish I was still there!!!!

Sandy Tyree

Sandy Tyree

Ocala FL


April 15, 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.

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

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