USA Gulf Coast Florida Key West Listing #10731

Tradewinds - Key West, FL

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30 reviews
Max. occupancy: 12 4 King Bed, 2 Sofa Bed 4 bedrooms 2 bathrooms 4 dog max  (30 lb weight limit) 
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Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love?

Located half a block from all the excitement of Duval Street, you can walk to historical landmarks like the Key West Lighthouse and The Ernest Hemingway Home and Museum, then stroll south to look out to sea from Southernmost Point. A short walk north will reveal more bars and restaurants than you could hope for on an island this size!

Fuel your day with a home-cooked breakfast in your fully equipped kitchen, sip coffee in the tropical garden, and get a morning soak in the hot tub for some extra relaxation. Freshen up using the outdoor shower, have a barbecue using the gas grill, and kill some time browsing the free WiFi or surfing the flatscreen cable TV. A dog is welcome for a small nightly fee.

Put life on hold for a moment and settle into paradise with these two cottages on Key West - book today!

You must be 25 years or older to rent this property.




Heating & cooling

Central AC

Partial AC

House rules


Kitchen & dining





Beach access





Wireless router

On-site activities

Hot tub : Private


Gas grill : Private



30 reviews

Connor E. Mar 2022
The two cottages are perfectly situated for groups, with two king beds and a pullout couch in each, as well as a hot tub and grill! The location is very walkable to everything and an easy uber from the airport and golf course
Brenda H. Jan 2022
Vacasa we’re in touch continually to ensure there were no issues checking in and to confirm our needs were met.
We were a party of 8 and had a great time. Location was great and we walked everywhere. The cottages are exactly like pictures. It’s a little rustic and all in our party loved it and agreed we would stay at Tradewind Cottages again. We did. It use the hot tubs so no comment on those. It’s January in South FL so we had no issues with a/c.
George C. Aug 2021
These two houses fit our large group perfectly. And also perfectly located adjacent to Duval. Will be coming back here. Highly recommend
Heather J. Aug 2021
We had issues with the ACs in both houses. The bedroom ACs were so loud that they kept us awake but they at least cooled the rooms. The living room ACs in both houses could not keep those areas cool and the bathrooms were like saunas. If you need to use the pull out sofa in the living rooms be prepared to be hot all night. Although we did not intend on using the hot tub in the middle of summer, we did lift the top to check them out. One was full of sand, had missing pieces and a controller that was so worn that you could not tell what each button was for and the other had smelly cloudy water. Just fair warning if you are booking these because you want to use the hot tubs. Shame because they are quite cute and we liked the location. Also-just know that the streets are very narrow and it’s a bit of a challenge to pull into the driveway if you have a truck or SUV.
Manager response:
Hello Heather, we apologize for the issues you experienced during your stay. We are disappointed that they were not reported to us during your stay so our local team could address them and improve the quality of your stay. We hope to get the chance to impress you during a future stay.
Chip N. Jul 2021
The location is perfect. In the middle of everything. Just off Duval, up the street from the Hemingway museum, everything less than a mile away. Great layout of two cottages. Four total bedrooms, 2 bathrooms. Nice separation if needed. Only drawback was heat index was 102 and Air Conditioning struggled to keep up. Plus the Hot Tubs need some help, missing a few pieces. Also, two wifi setup, one worked, on didn't. The service was great, anything needed was just a call away, very responsive!
Carolyn C. May 2021
Location was great. Good and bad was bar on nearby corner - great happy hours but not so great for late night noise. House needs a little attention to maintenence do to termites swarming.
Abby M. May 2021
We rented the Leeward and Windward cottages for 7 nights. Along with our stay were some positives and negatives.

This property is good for adults or families visiting that want to travel together, but spread out with separate spaces.

Not good for light sleepers as the front bedrooms will hear the party animals coming/going all night along with a bright security light that comes on each time a passerby comes along (every 5 minutes).
We didn't use the hot tubs as it was super hot already in April. I'm not sure if that added expense of a hot tub fee is worth it.
I want to note this is the first rental that didn't have a washer and dryer for us to use throughout the stay.
Communication with Vacasa pre-stay was pretty painful and took a while to get back. Utilizing messaging within the app didn't work well. Be prepared to pick up the phone.
Kimberly S. Feb 2021
I organized a girl getaway. There were 10 of us. The 2 cottages were perfect. We were able to go back and forth to both places The beds and bedrooms were huge. I slept on the couch and have no complaints at all. Walking distance to everything. The hot tubs constantly had someone in them. Which was perfect with it being a little chilly the weekend we went. Definitely recommend for small AND/OR large group.
Eddie R. Nov 2020
We loved being so close to the action! Walked everywhere. Rented a golf cart one day to ride around in! Enjoyed the hot tub as well!
Amy C. Jul 2020
These are super cute and in a good central location. Houses are in good condition. I have a few suggestions to make it great- the windows in the front there are some broken pains so it rattles and makes it easier to hear then street noise. Furniture could definitely use some updating and the outside foliage need to be trimmed. These homes were very clean and well stocked with towels and even beach towels which was great for us since we flew in. If I cane back to Key West I would stay here again.
Manager response:
Thank you for your review, Amy. We are glad you enjoyed this home and we appreciate you bringing these issues to our attention. We will work with our local team to ensure these items are corrected for future guests, and we hope to host you again in the near future!
Amy B. Jan 2020
Cute cottages, have some age on them but very clean. Could definitely use some new mattresses and new couches, sagging in the middle. Loved hanging out on the front porch and in the back yard, especially with the hot tub! Excellent location, very convenient for Duval St., beach, parks, etc. Would definitely rent again.
Manager response:
Thank you for staying with us and telling us about your experience. The owners have plans to replace the sofas, and we will be flipping the mattresses. We hope to see you again!
Kristina R. Oct 2019
We visited key west for the marathon. Coming home to these cute houses and comfy beds with hot hot tubs after the run made the whole experience so much better!!!!
Jean-Paul L. Oct 2019
The houses were clean and well layed out. The location was perfect
Penny F. Jun 2019
We loved the cottages! They had everything we needed, we brought our adult children and their significant others and our parents. Everyone was comfortable! We had plenty of room, loved the hot tubs, grill worked perfectly and the outdoor shower was a plus!
Melinda P. Mar 2019
Both cottages were perfect for four couples. The location is friendly and walking distance to most venues. The mattresses are a little dated so prepare accordingly.
William D. Sep 2018
Quiet part of town. Bar across the street gets a little loud but, AC units inside run constantly so they pretty much drown out the noise. Well kept, clean and has just about everything you need. One suggestion would be to keep salt and pepper shakers in the house for tenants to use. Overall, great location to DuVal Street. Process was very easy and staff was friendly and helpful!
Christopher W. Feb 2018
We loved having the two cottages next to each other. Convenient location, clean neat home. We would definitely stay again!
Chukwuka A. Feb 2018
Company Sales Meeting in KW and we had an amazing time. The property was great for 4 people and could sleep four couples perfectly.
I would recommend this location to anyone wanting to stay close to Duvall St and all the fun places around there.
James S. Jan 2018
The houses are really cute and so close to everything! They are right across the street from a happening bar and they party all night!! We went over and joind in the fun, but if you're looking for peace and quiet you may want to stay further from duvall st!
Colin C. Jan 2018
Great Home and location.
Anthony C. Dec 2017
Nice place to stay for a large group