Tradewinds Resort

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An intimate Old Florida-style beach getaway!
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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 trees, 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.

10/24/2026

🎣 Discover Historic Cortez Village! ⚓

Did you know that just minutes from Tradewinds is the historic Cortez Village, which offers a glimpse into Old Florida? Settled in 1880 by fishing families from North Carolina, it remains one of the state’s few working fishing villages today.

Visit the Florida Maritime Museum, explore historic buildings, learn about the area’s fishing heritage, and enjoy some of the freshest local seafood around.

🌴 Add Cortez Village to your Tradewinds Stay!

10/22/2026

🌴Sunsets are our love language 🌴 Show us your sunset pics, we're basically addicted to them on this island 🤣

10/20/2026

Sit back and relax in Tradewinds #21, the ultimate retreat that combines comfort and tranquility. This perfectly situated 1-bedroom haven offers all the comforts of home, with an amazing Bay view that will leave you breathless. Imagine waking up to the sound of tropical birds and falling asleep to the gentle lapping of the Bay. Whether you're looking to escape the hustle and bustle of city life or simply need a romantic getaway, this cozy abode has everything you need to unwind and recharge.

10/16/2026

🎣Fishing🎣
Looking for a little excitement during your relaxing vacation?
Check out the amazing fishing options on and around the island.
Whether you want to fish from the dock with a cold beverage or experience the wonder of offshore fishing, Anna Maria Island has plenty of options.
, Captain Pete's Charters

10/14/2026

🍦National Dessert Day🍦
Warning: eating desserts on vacation doesn't count, right?
What's your go-to guilty pleasure? Spill the beans, and bonus points if you can tell us where to find it on the island! 🍰

10/12/2026

🌴 Check Out Our Beautiful Rentals at Tradewinds Beach Resort! 🌴

Looking for the perfect Anna Maria Island getaway? ☀️🌊 Our owners take great pride in their individually owned units, each offering its own unique style, comfort, and charm.

Whether you’re planning a romantic escape, a family vacation, or just some much-needed beach time, we have a rental waiting for you! 🏖️

✨ Click the link to explore our available units, find your favorite, and then give us a call to book your stay!

https://booking.annamariaislandresorts.net/rentals

📞 We’d love to help you plan your next island getaway.

10/10/2026

💚 World Mental Health Day 💚

Today is a reminder that taking care of your mental health is just as important as taking care of your physical health.

Sometimes, a little change of scenery can do wonders. 🌴 Take a walk on the beach, listen to the waves, sit beneath the palms, enjoy the Florida sunshine, or simply give yourself permission to slow down and breathe.

We’re lucky to be surrounded by peaceful gardens, swaying palms, beautiful water views, and the calming beauty of Anna Maria Island. 🌊☀️

Today, take a moment for you. Check in with yourself, check in with someone you love, and remember that it’s okay to slow down.

💚 Be kind to your mind.

10/08/2026

🌴 THIS OR THAT: TRADEWINDS EDITION! 🌴

You’ve checked into Tradewinds Beach Resort, the sun is shining, and it’s time to relax… but where are you heading first? 😎

🏖️ BEACH — toes in the sand, Gulf breeze and beautiful Anna Maria Island views.

OR

🏊 POOL — grab a lounger, take a refreshing dip and settle in for a relaxing afternoon.

👇 Which are you choosing — BEACH or POOL?

Call us today at 941-779-0010 to book your perfect stay
And yes… “BOTH” is absolutely an acceptable answer! 😂🌴☀️
# beachvacation

10/06/2026

🌴 Welcome to Tradewinds Unit #24! 🌴
Your cozy Anna Maria Island getaway is waiting! 💙 Unit #24 has everything you need to settle in, relax, and enjoy island time.
🏡 Comfortable 1-bedroom retreat
🍳 Full kitchen for meals and snacks at home
🛋️ Cozy living area
🌴 Private porch—the perfect spot for morning coffee or an evening drink
💦 Just steps from the beautiful bayfront grounds
🏖️ Easy access to all the sunshine, sand, and fun Anna Maria Island has to offer!
Bright, comfortable, and full of island charm, Tradewinds Unit #24 is ready for your next beach escape. 🌊☀️
📍 Tradewinds Beach Resort | Anna Maria Island
📞 Book your stay and start counting down to island time!
https://booking.annamariaislandresorts.net/rentals/tradewinds-unit-tw24

09/23/2026

☕️🌴 GOOD MORNINGS START HERE! 🌴☕️
Looking for the perfect way to start your day on Anna Maria Island? Stop by Anna Maria Island Coffee Shack! ☀️🌊
This privately family-owned little gem is serving up breakfast, lunch, great coffee, and plenty of island sunshine. Whether you're grabbing a cup of coffee before heading to the beach, enjoying breakfast with the family, or stopping in for lunch, you'll always get that friendly, welcoming feeling that makes a place special. ❤️
👨‍👩‍👧‍👦 Kid-friendly
☕️ Fresh coffee & breakfast
🥪 Breakfast & lunch
🌴 Family owned & operated
❤️ The owners are absolutely wonderful!
📍 5500 Marina Drive
Holmes Beach, FL 34217
🕗 Open:
Monday • Wednesday • Thursday • Friday
7:00 AM – 2:00 PM
Saturday 8:00 a.m- 2:00 p.m
Sunday 8:00 a.m-1:00 p.m.
Come grab a cup, soak up some sunshine, and start your morning the island way. 🌅☕️🏝️
Anna Maria Island Coffee Shack — where good coffee and good people come together. ❤️

Address

1603 Gulf Drive N
Bradenton Beach, FL
34217

Website

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

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