For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the listed minimum stay, and no night in between is marked Not Available. Prices are nightly rates before taxes, cleaning and other fees. The table covers every date through Feb 6, 2027; a date missing from the table has no published nightly rate.
Escape to Tradewinds Key West Style #9 on Anna Maria Island! Enjoy a romantic getaway in this cozy one-bedroom condo, steps from the beach and Bridge Street's charm!
Dated quotes with taxes and fees, and bookings, through the Kismet guest MCP at https://kismet.travel/c/ami-locals/mcp (Streamable HTTP, JSON-RPC 2.0 over POST; no account or API key for public reads).
Amenities
Steps from the Beach · Community Amenities · Near Bridge Street · Ideal for Couples
Location
3 mins to Bradenton Beach · 5 mins to Bridge Street · 9 mins to Anna Maria Island Trolley Stop
Reviews
4.7/5 from 6 reviews — "Hannah was a pleasure to host
My family had a great stay" · Read all reviews
Policies
No pets · Check-in 4:00 PM · Check-out 10:00 AM
FAQ
Is this property pet-friendly? No, pets are not allowed.
How far is this from local attractions? 3 mins to Bradenton Beach, 5 mins to Bridge Street, 9 mins to Anna Maria Island Trolley Stop.
What are check-in and check-out times? Check-in: 4:00 PM, Check-out: 10:00 AM
Tradewinds Key West Style #9 by AMI Locals Vacation Rental License #TPL24-000119, CND5105469
Welcome to Tradewinds Key West Style #9, a cozy 1-bedroom, 1-bathroom island escape located in the heart of Bradenton Beach on Anna Maria Island! Just a 3-minute stroll from the Gulf’s sugar-white sands, this adorable condo is perfect for couples seeking a peaceful retreat near top restaurants, shopping, and the vibrant Bridge Street district. Nestled in the charming Tradewinds resort community, you'll enjoy easy access to a heated pool, fishing dock, and picnic area, all designed to elevate your tropical escape.
Highlights • 3-Minute walk to Beach • 1 Bedroom / 1 Bathroom • King Bed, Full Sleeper Sofa • Community Pool • Community Fishing Dock • Picnic Area with BBQ Grill • Near Bridge Street and Anna Maria Island Trolley Stop • Ideal for Couples or Solo Travelers • 1 Parking space
Tradewinds Key West Style #9 is part of a quaint resort-style community that brings comfort and convenience to your stay. Take a dip in the seasonally heated pool with a view of the sparkling Bay, stroll to the community dock for fishing or stunning sunsets and make use of the outdoor showers after a beach day. Fire up the BBQ grill in the shaded picnic area for a relaxed evening under the palms. You're also just a short walk to the Anna Maria Island trolley stop, offering free and easy transportation to explore the island’s beaches, piers, and eateries.
Step inside a beachy, Key West–inspired living space designed for ultimate relaxation. The cozy seating area with a plush sofa and armchair sets the tone for romantic movie nights on the large TV. The fully equipped kitchen includes modern appliances, cookware, and a charming breakfast table, perfect for slow mornings with coffee or casual dinners after a day in the sun.
The serene bedroom features a king-size bed with crisp linens and island-inspired decor, offering a tranquil place to unwind and recharge. The bathroom is fitted with a shower and tub combination, giving you the option for a refreshing rinse or a relaxing soak. For additional guests, a full-size sleeper sofa is available in the living room, making this unit both versatile and comfortable.
Room Details • Primary Bedroom: King bed • Living Room: Full-size sleeper sofa
Looking for a romantic beach retreat or a relaxing solo escape? Tradewinds Key West Style #9 is the perfect spot. Stay just steps from the beach, enjoy the peaceful comforts of the Tradewinds community, and immerse yourself in everything Anna Maria Island has to offer.
Book your island escape today and experience the charm of Florida’s Gulf Coast like never before!
- This home is managed by AMI Locals, an Anna Maria Island property management company.
This property does not allow pets of any kind.
1 car maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.
We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details.
Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions, including fines and/or termination of your rental agreement without refund.
Availability Calendar
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Swipe for Availability
Bedding
Bedroom 1
Sleeps: 2
1 King
Attached Bathroom
Amenities 60
Community Amenities
Shared BBQ Grill
Shared Pool
Essentials
Air Conditioning
Beach Chairs Provided
Beach Towels Included
Bed Linens
Free Wifi
Hair Dryer
Heating
Hospital Close By
Hot Water
Long Term Stays Allowed
No Pets Allowed
Pack 'n Play
Private Entrance
Required Stairs
Towels
Wifi
Exterior
BBQ Area
Covered Deck
Fishing Dock
Outdoor Dining Area
Outdoor Seating
Shared Spaces
Sun Loungers
Fun and Entertainment
Smart TV
TV
Home Safety
Carbon Monoxide Detector
Contactless Check-In
Deadbolt Lock
Fire Extinguisher
Keyless Lock
Smoke Detector
Interior
Bathtub
Ceiling Fans
Clothes Hangers
Clothing Storage
Full Kitchen
Living Room
Kitchen
Baking Sheet
BBQ Utensils
Blender
Coffee Maker
Dining table
Dishes and Utensils
Dishwasher
Microwave
Oven
Pots and Pans
Refrigerator
Stove
Toaster
Wine Glasses
Location
Anna Maria Island
Bay Front
Beach Access Nearby
Bradenton Beach
Less than a 5-minute walk to the beach
Walking Distance to Beach
Parking
One (1) Parking Space
Reviews4.9(14)
5
My family had a great stay!
Hannah
- Posted: 8/16/2026
We’re so glad your family had a great stay at Tradewinds Key West Style #9 by AMI Locals, Hannah! Thank you for choosing us for your Anna Maria Island getaway and for taking a moment to share your experience. We hope to welcome your family back to Tradewinds Key West Style #9 for another relaxing and memorable island vacation!
AMI Locals staff
5
Clean and perfect for our stay. Right across from beach. Management was very helpful and responsive. Will come back!
Jennifer
- Posted: 8/10/2026
We’re so glad Tradewinds Key West Style #9 by AMI Locals was the perfect fit for your stay, Jennifer! Having the beach right across the way makes it easy to enjoy every bit of island time, and we’re happy the home was clean and comfortable for your visit. We’re also grateful for your kind words about our team and their responsiveness. Thank you for choosing Tradewinds Key West Style #9 and for sharing your experience. Knowing you plan to come back is the best compliment, and we look forward to welcoming you again soon!
AMI Locals staff
5
Had a wonderful stay! Beautiful location and responsive hosts. Would definitely stay again!
Ariana
- Posted: 7/19/2026
Some getaways are memorable because everything just falls into place, and we're so glad that was your experience at Tradewinds Key West Style #9 by AMI Locals. It's wonderful to hear you enjoyed the beautiful location and that our team was responsive whenever you needed us. Thank you for your kind words and recommendation, Ariana. We'd be delighted to welcome you back to Tradewinds Key West Style #9 for another relaxing stay on the island.
AMI Locals staff
5
Beautiful accommodations. Extremely clean. Very helpful staff. Very convenient location. Would highly recommend.
Jason
- Posted: 7/9/2026
A stay is even more memorable when everything comes together so effortlessly, Jason. We're delighted Tradewinds Key West Style #9 by AMI Locals checked all the boxes with its beautiful accommodations, spotless condition, and convenient location. It's especially rewarding to hear our team helped make your experience an enjoyable one. We truly appreciate your recommendation and hope to welcome you back for another relaxing island getaway in the near future.
AMI Locals staff
5
Best part of our stay was how close to beach we were!! Loaded up our wagon with the most comfortable beach chairs, cooler and beach bags and we're waterside within 3 minutes!!! Restaurants walkable. Sunsets, unmatched.
Julie
- Posted: 6/21/2026
Some of the best days on AMI start with a short walk to the beach and end with an unforgettable sunset, Julie! We're so glad Tradewinds Key West Style #9 by AMI Locals made it easy to enjoy every moment of your island getaway. Having beach chairs, a wagon, and a cooler ready to go makes those quick trips to the shore even better, and being within walking distance of local restaurants is always a bonus.. Those AMI sunsets really are something special, and we're happy you were able to experience them. Thank you for staying with us—we'd love to welcome you back for more beach days, evening strolls, and island sunsets!
AMI Locals staff
5
An amazing place to stay. No complaints. Would stay again
Rebecca
- Posted: 6/14/2026
Short, sweet, and exactly what we love to hear, Rebecca. We're so glad Tradewinds Key West Style #9 by AMI Locals provided such a great stay and that everything met your expectations. Sometimes the best vacations are the ones where everything just falls into place and you can simply enjoy your time on the island. Thank you for choosing to stay with us. We'd be delighted to welcome you back for another relaxing AMI getaway anytime!
AMI Locals staff
5
This place was great and we loved the pool by the bay and short walk to the beach. The unit was very clean and comfortable and my wife and I had a relaxing time. We would recommend this location and unit. There is a good smokehouse restaurant right around the corner that you should try!
Joe
- Posted: 6/10/2026
A relaxing getaway with bay views, beach walks, and great local food is hard to beat, Joe! We're so glad you and your wife enjoyed your time at Tradewinds Key West Style #9 by AMI Locals. Having the bayfront pool just steps away and the beach within an easy walk gives you the best of both worlds during your stay. We're happy to hear the unit was clean, comfortable, and provided the perfect place to unwind and enjoy some quality time together. And discovering a favorite local restaurant around the corner is always a bonus! Thank you for the recommendation and for choosing to stay with us. We hope to welcome you back for more island sunsets, beach days, and relaxing moments on AMI soon!
AMI Locals staff
5
The unit was perfect for our stay. Clean, well stocked, and conveniently located.
Linda
- Posted: 5/10/2026
Tradewinds Key West Style #9 by AMI Locals sounds like it checked all the right boxes for your trip, Linda! Clean, well-stocked, and in a convenient location makes it easy to settle in and enjoy everything AMI has to offer. Really glad it was a great fit for your stay, and we’d love to host you again soon!
AMI Locals staff
4
It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences.
Valerie T.
- Posted: 4/13/2026
That’s the kind of island wandering we love, Valerie. So glad you enjoyed your stay at Tradewinds Key West Style #9 by AMI Locals—being close to the beach and able to stroll to grab a bite just makes everything feel easy. Cruising around the island and checking out all the little spots is half the fun, and it’s great to hear the cottage had everything you needed to kick back and relax in between. Come back and explore a little more next time and we’ll save you a spot in the sunshine!
AMI Locals staff
5
Great location
Location
N/A
Deborah
- Posted: 3/6/2026
5
Enjoyable stay. No complaints.
Chase
- Posted: 8/5/2025
Thank you for the positive review, Chase. We're pleased to hear that you had an enjoyable stay with us. We look forward to welcoming you back in the future with AMI Locals! Thank you, AMI Locals
AMI Locals staff
5
Wife's birthday vacation
It was great! Check in was super easy and anything you would need is nearby.
Thomas N.
- Posted: 7/27/2025
Thank you so much Thomas! We are so glad you all enjoyed this amazing celebration!
AMI Locals staff
5
Had a wonderful stay. The place was super clean and the location was perfect. Close to the beach and walking distance to several restaurants.
Jaecey
- Posted: 7/23/2025
Thank you so much for the wonderful review, Jaecey! We're thrilled to hear that you had a great stay and that the location and cleanliness of the property met your expectations. It's great to know that you were able to enjoy the nearby beach and restaurants. We truly appreciate your feedback and look forward to hosting you again in the future!!
AMI Locals staff
5
The room was clean and comfortable. Had a great stay!
Chris
- Posted: 7/14/2025
Appreciate you sharing your experience, Chris! It's great to know the room offered just the right comfort and cleanliness. We’d love to have you back for another easy and enjoyable stay!
AMI Locals staff
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5 People have considered this property in the last 24 hours
We’re so glad your family had a great stay at Tradewinds Key West Style #9 by AMI Locals, Hannah! Thank you for choosing us for your Anna Maria Island getaway and for taking a moment to share your experience. We hope to welcome your family back to Tradewinds Key West Style #9 for another relaxing and memorable island vacation!
AMI Locals staff
5
Clean and perfect for our stay. Right across from beach. Management was very helpful and responsive. Will come back!
Jennifer
Posted: 8/10/2026
We’re so glad Tradewinds Key West Style #9 by AMI Locals was the perfect fit for your stay, Jennifer! Having the beach right across the way makes it easy to enjoy every bit of island time, and we’re happy the home was clean and comfortable for your visit. We’re also grateful for your kind words about our team and their responsiveness. Thank you for choosing Tradewinds Key West Style #9 and for sharing your experience. Knowing you plan to come back is the best compliment, and we look forward to welcoming you again soon!
AMI Locals staff
5
Had a wonderful stay! Beautiful location and responsive hosts. Would definitely stay again!
Ariana
Posted: 7/19/2026
Some getaways are memorable because everything just falls into place, and we're so glad that was your experience at Tradewinds Key West Style #9 by AMI Locals. It's wonderful to hear you enjoyed the beautiful location and that our team was responsive whenever you needed us. Thank you for your kind words and recommendation, Ariana. We'd be delighted to welcome you back to Tradewinds Key West Style #9 for another relaxing stay on the island.
AMI Locals staff
5
Beautiful accommodations. Extremely clean. Very helpful staff. Very convenient location. Would highly recommend.
Jason
Posted: 7/9/2026
A stay is even more memorable when everything comes together so effortlessly, Jason. We're delighted Tradewinds Key West Style #9 by AMI Locals checked all the boxes with its beautiful accommodations, spotless condition, and convenient location. It's especially rewarding to hear our team helped make your experience an enjoyable one. We truly appreciate your recommendation and hope to welcome you back for another relaxing island getaway in the near future.
AMI Locals staff
5
Best part of our stay was how close to beach we were!! Loaded up our wagon with the most comfortable beach chairs, cooler and beach bags and we're waterside within 3 minutes!!! Restaurants walkable. Sunsets, unmatched.
Julie
Posted: 6/21/2026
Some of the best days on AMI start with a short walk to the beach and end with an unforgettable sunset, Julie! We're so glad Tradewinds Key West Style #9 by AMI Locals made it easy to enjoy every moment of your island getaway. Having beach chairs, a wagon, and a cooler ready to go makes those quick trips to the shore even better, and being within walking distance of local restaurants is always a bonus.. Those AMI sunsets really are something special, and we're happy you were able to experience them. Thank you for staying with us—we'd love to welcome you back for more beach days, evening strolls, and island sunsets!
AMI Locals staff
5
An amazing place to stay. No complaints. Would stay again
Rebecca
Posted: 6/14/2026
Short, sweet, and exactly what we love to hear, Rebecca. We're so glad Tradewinds Key West Style #9 by AMI Locals provided such a great stay and that everything met your expectations. Sometimes the best vacations are the ones where everything just falls into place and you can simply enjoy your time on the island. Thank you for choosing to stay with us. We'd be delighted to welcome you back for another relaxing AMI getaway anytime!
AMI Locals staff
5
This place was great and we loved the pool by the bay and short walk to the beach. The unit was very clean and comfortable and my wife and I had a relaxing time. We would recommend this location and unit. There is a good smokehouse restaurant right around the corner that you should try!
Joe
Posted: 6/10/2026
A relaxing getaway with bay views, beach walks, and great local food is hard to beat, Joe! We're so glad you and your wife enjoyed your time at Tradewinds Key West Style #9 by AMI Locals. Having the bayfront pool just steps away and the beach within an easy walk gives you the best of both worlds during your stay. We're happy to hear the unit was clean, comfortable, and provided the perfect place to unwind and enjoy some quality time together. And discovering a favorite local restaurant around the corner is always a bonus! Thank you for the recommendation and for choosing to stay with us. We hope to welcome you back for more island sunsets, beach days, and relaxing moments on AMI soon!
AMI Locals staff
5
The unit was perfect for our stay. Clean, well stocked, and conveniently located.
Linda
Posted: 5/10/2026
Tradewinds Key West Style #9 by AMI Locals sounds like it checked all the right boxes for your trip, Linda! Clean, well-stocked, and in a convenient location makes it easy to settle in and enjoy everything AMI has to offer. Really glad it was a great fit for your stay, and we’d love to host you again soon!
AMI Locals staff
4
It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences.
Valerie T.
Posted: 4/13/2026
That’s the kind of island wandering we love, Valerie. So glad you enjoyed your stay at Tradewinds Key West Style #9 by AMI Locals—being close to the beach and able to stroll to grab a bite just makes everything feel easy. Cruising around the island and checking out all the little spots is half the fun, and it’s great to hear the cottage had everything you needed to kick back and relax in between. Come back and explore a little more next time and we’ll save you a spot in the sunshine!
AMI Locals staff
5
Great location
Location
N/A
Deborah
Posted: 3/6/2026
5
Enjoyable stay. No complaints.
Chase
Posted: 8/5/2025
Thank you for the positive review, Chase. We're pleased to hear that you had an enjoyable stay with us. We look forward to welcoming you back in the future with AMI Locals! Thank you, AMI Locals
AMI Locals staff
5
Wife's birthday vacation
It was great! Check in was super easy and anything you would need is nearby.
Thomas N.
Posted: 7/27/2025
Thank you so much Thomas! We are so glad you all enjoyed this amazing celebration!
AMI Locals staff
5
Had a wonderful stay. The place was super clean and the location was perfect. Close to the beach and walking distance to several restaurants.
Jaecey
Posted: 7/23/2025
Thank you so much for the wonderful review, Jaecey! We're thrilled to hear that you had a great stay and that the location and cleanliness of the property met your expectations. It's great to know that you were able to enjoy the nearby beach and restaurants. We truly appreciate your feedback and look forward to hosting you again in the future!!
AMI Locals staff
5
The room was clean and comfortable. Had a great stay!
Chris
Posted: 7/14/2025
Appreciate you sharing your experience, Chris! It's great to know the room offered just the right comfort and cleanliness. We’d love to have you back for another easy and enjoyable stay!
