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Anna Maria Island Vacation

Relax on the beach with complimentary beach chairs, beach towels and umbrellas. Relax by the Bayfront pool or catch dinner from the private fishing dock.

A Range of Accommodations

Accommodations range from our intimate south cottages to expansive 2 bedroom units. All our units offer a full kitchen.

Laid Back Anna Maria

Anna Maria Island offers a variety of activities and restaurants to keep everyone happy. Enjoy everything from jet skiing, parasailing, fishing or just relaxing on the beach.
  • Tradewinds Cottages
  • Tradewinds Pool
  • Tradewinds Cottage
  • Tradewinds Cottage
  • Tradewinds Cottage
  • Tradewinds Cottage
  • Tradewinds Entrance
  • Tradewinds Dock
  • Tradewinds Courtyard
  • Tradewinds bayfront buidling
Stay 4 Nights Pay For 3

May 1st to July 31st Arriving Sunday and Monday only

August 1st to December 31st Arriving any day

All nights must be in same unit. Black out dates apply and include holidays.

Great resort!

“We stayed in the Deluxe Garden Apartments. The place was spacious, clean and the location was perfect! The resort included beach toys, umbrellas and beach chair. Staff was friendly and quick to answer questions. We booked our next stay prior to leaving. I would highly recommend this resort!”
Date of stay: December 2020
Room Tip: We enjoyed the deluxe garden apt with a partial view

Jen L


Stayed here on the Penthouse condo. It was wonderful big clean. The first night A/C broke down but we called immediately and was fixed within 2 hrs. I had no other issues. The staff was nice. I loved the pier so the kids could go fishing. The beach chairs and umbrellas were old but did the work. Will definitely stay here again.
Date of stay: August 2020
Trip type: Traveled with family
Arleen R

4th time staying here – and it was the best time yet!

For this trip, we upgraded to the bayfront 2-bedroom. I’m so glad we did! The views are amazing, the decor is lovely, and there is plenty of space. We were able to watch the boats, the sunrise, and some dolphins. It was very quiet and serene … with a quick walk to the beach and restaurants. We enjoyed sitting on the spacious porch sipping cocktails. The kitchen is equipped with everything you could possibly need. We will definitely be back! Bonus: it’s pet-friendly; we love traveling with our pup!

Date of stay: August 2020

Room Tip: Bayfront 2-bedroom (I believe it’s #23)

Great stay

This was our 3rd visit. We stayed in the deluxe north cottage #2. The room was decorated beautifully. Love that we can bring our dog with us. It’s in a great location too. Would definitely recommend this resort.

Date of stay: September 2020

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