Tradewinds Resort

An intimate Old Florida-style beach getaway!
(290)

Tradewinds Beach Resort is located on quaint Anna Maria Island in the Gulf of Mexico off Southwest Florida's fabled Sun Coast. This charming, old-fashioned resort has pastel cottages covered with tangles of jasmine and bougainvillea that look like something seen on a postcard a century ago. The romantic cottages line both sides of a private street that ends at a large heated pool set among palm tr

ees, and a fishing pier that juts into Sarasota Bay. Just across Gulf Drive, at our sister resort of Tortuga, is a private white sand beach beside that glorious turquoise water you're coming for - and sunset views that promise to break your heart with their beauty.

09/03/2026

🧔🌴 HAPPY WORLD BEARD DAY FROM TRADEWINDS BEACH RESORT! 🌴🧔

Today we’re celebrating beards, beaches & island breezes! 😎🌊

Whether your beard is short, long, perfectly groomed, or living its best island-life after a day of saltwater and sunshine — today is your day! ☀️🏖️

So grab your shades, kick off your flip-flops, and let that beard blow in the Anna Maria Island breeze. 🌴

🧔 No beard? No problem. You’re still invited to the beach! 😂

📞 Call 941-779-0010 to book your Tradewinds getaway!

08/31/2026

🌴☀️ ISLAND TIME IS CALLING… AND TRADEWINDS BEACH RESORT IS ANSWERING! 🌊😎

Ready to swap traffic, chores, and alarm clocks for flip-flops, sunshine, and toes in the sand? 🩴🏖️

At Tradewinds Beach Resort, your Anna Maria Island getaway is all about slowing down, soaking up the Florida sunshine, and asking the really important questions…

🍹 Beach or pool?
🌅 Sunrise or sunset?
🐚 Shell hunting or absolutely nothing?
😎 One more day? ALWAYS!

Come enjoy the laid-back island life and make Tradewinds your home away from home. 🌴💙

📞 Call 941-779-0010 to book your getaway!

Because sometimes the best plans are simply… GO TO THE BEACH! 🌊☀️

08/29/2026

🔥☀️ IT’S HOT ON ANNA MARIA ISLAND… SO WE’RE TURNING UP THE HEAT ON OUR SAVINGS! ☀️🔥

We thought our discounts should match the island vibe, so check out these SCORCHING HOT DEAL! 🌴🌊

🔥 Stay 2 nights — Get 10% OFF
🔥 Stay 3 nights — Get 15% OFF
🔥 Stay 4+ nights — Get ONE NIGHT FREE! 🤩

Pack your flip-flops, grab your sunscreen, and escape to Anna Maria Island! 🏖️🍹

📞 CALL 941-779-0010 TO BOOK
This sizzling special is available by phone only, so give us a call and snag your getaway!

🔥 The island is hot. The deal is hotter. 🔥

08/26/2026

🐾 Happy National Dog Day from Tradewinds and Anna Maria Island Resorts! 🐾

There’s nothing better than a getaway—except a getaway with your best four-legged friend! 🐶🌴☀️

Today we’re celebrating all the pups who fill our lives with love, loyalty, wet kisses, and plenty of sandy paw prints. ❤️🐾

Several of our units are pet-friendly, so your furry family member can join you for an unforgettable Anna Maria Island vacation.

📸 Celebrating National Dog Day with us? Drop a photo of your pup in the comments—we’d love to see them!

🐕🌊 Happy National Dog Day!

08/21/2026

🌴 Your Own Little Slice of Paradise!☀️

Looking for a little more room for your island getaway? Cottage #35 is our two-bedroom cottage, offering plenty of space to relax, reconnect, and enjoy your time on Anna Maria Island.

This spacious cottage features a king bed in the primary bedroom, a queen bed in the second bedroom, and a queen sleeper sofa in the living area, along with 1½ bathrooms, a full kitchen, dining area, and comfortable living room.

One of the highlights of Cottage #35 is the screened porch at the front of the cottage—a wonderful space to gather, enjoy the fresh island air, and spend time together.

With its inviting layout and cozy atmosphere, Cottage #35 truly feels like your own little slice of paradise. Whether you're traveling with family or friends, you'll have the space and comfort to make your island stay one to remember.

🌊 Come find your little slice of paradise at Tradewinds!
https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw35

08/19/2026

🌴 South Cottage #28! ☀️

Looking for a cozy place to call home during your Anna Maria Island getaway? South Cottage #28 offers a comfortable one-bedroom retreat with everything you need for a relaxing stay.

The cottage features a queen bed in the bedroom and a queen sleeper sofa in the living room, along with a full kitchen, dining area, and comfortable living space.
However you choose to spend your days here, Cottage #28 is a welcoming place to return to at the end of the day.

🌊 Come experience the charm of island living at Tradewinds!
https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw28

08/17/2026

🌴A Cozy South Cottage Getaway! ☀️

Make yourself at home in South Cottage #25, a charming one-bedroom retreat at Tradewinds that gives you everything you need for a comfortable island escape.

This cozy cottage features a queen bed in the bedroom and a queen sleeper sofa in the living room, making it a great choice for couples, friends, or a small family. You'll also have a full kitchen, dining area, and comfortable living room, giving you plenty of space to settle in and enjoy your stay.

Whether you're spending your days at the beach, exploring the island, or enjoying time together at the resort, this cottage gives you a comfortable place to come back to at the end of the day.

🌊 Pack your bags, bring your favorite people, and get ready for your island escape!
https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw25

08/13/2026

🌊 **Your Own Little Piece of Bayfront Paradise!** 🌴

Say hello to Bayfront Cottage #22, one of just two one-bedroom bayfront cottages at Tradewinds! If beautiful waterfront views are at the top of your vacation wish list, this cottage delivers.

With the same comfortable layout as our North Cottages, #22 features a king bed, queen sleeper sofa, full kitchen, living area, and dining space—giving you all the comforts you need for your island stay.

But the real highlight? The bay is right outside your door. Wake up to beautiful waterfront scenery, watch the boats pass by, and enjoy the peaceful atmosphere that makes Anna Maria Island so special.

Whether you're looking for a relaxing retreat or a home base for an adventure-filled island getaway, Cottage #22 puts you right where you want to be.

✨Bayfront views. Island vibes. Unforgettable memories.
https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw22

08/11/2026

🌅 Wake Up to Beautiful Bayfront Views! 🌴

Looking for something a little extra special for your island getaway?Bayfront Cottage #21 is one of only two one-bedroom bayfront cottages we offer at Tradewinds—and the views are something you won't want to miss!

This cozy cottage features the same comfortable layout as our North Cottages, with a king bed, queen sleeper sofa, full kitchen, living area, and dining space. But what truly sets #21 apart is its beautiful bayfront setting, giving you a front-row seat to the natural beauty of the island.

Imagine stepping outside and taking in the sparkling waters of the bay, watching the colors change throughout the day, and ending your evening surrounded by the peaceful beauty of the waterfront.

✨ For those who want their island getaway to come with a view, this is the perfect choice.

https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw21

08/09/2026

🌴 Poolside Convenience Meets Island Charm! ☀️

Welcome to North Cottage #20, a cozy one-bedroom retreat in a prime location at Tradewinds. This cottage is the closest North Cottage to our bayfront pool, putting you just steps away from one of the best spots on the property to enjoy the Florida sunshine.

With a comfortable king bed, queen sleeper sofa, full kitchen, living area, and dining space, Cottage #20 gives you the comforts of home while keeping you close to all the fun. Whether you're heading to the pool for a refreshing swim, making your way to the beach, or exploring everything Anna Maria Island has to offer, you'll love having such easy access to it all.

✨ A great location, a comfortable cottage, and plenty of island adventures just outside your door.

https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw20

Address

1603 Gulf Drive N
Bradenton Beach, FL
34217

Website

https://www.annamariaislandresorts.net/tradewinds-beach-resort

Alerts

Be the first to know and let us send you an email when Tradewinds Resort posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Tradewinds Resort:

Want your business to be the top-listed Hotel in Bradenton Beach?