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Tradewinds - Nightly Group Unit

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4 Bedrooms
2 Bathrooms
Parking: 
2 Private Parking Spots
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Description

Tradewinds is comprised of the Leeward Isle and Windward Isle

Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your party can book these cottages for a relaxing vacation, just steps from Duval Street.

Tradewinds is comprised of the Leeward Isle and Windward Isle, which can also be booked as individual 2 bedroom/1 bathroom homes.

Key West Vacation Rentals typically releases all minimum night stay requirements within 60 days of the arrival date. Otherwise, our minimum night requirements are as follows:

- January thru April - 5 night minimum
- May thru mid - December - 3 night minimum
- Fantasy Fest Week - (late October) - 7 night minimum
- Christmas & New Years - 7 night minimum
- Special Holidays and Events may have up to 7 night minimums

Our software is designed to fill in small gaps between reservations that are outside of 60 days. Feel free to call our office for more info or special requests

Individual making the reservation must be 25 years or older with proper identification and be an occupant of the property

Amenities

  • Deck
  • Patio
  • Gas Grill
  • Outdoor Shower
  • 2 Private Hot Tubs
  • Near Beach
  • 1 Block from Duval
  • Old Town
  • Air Conditioning
  • Ceiling Fans
  • Linens
  • Ironing Board
  • Free Wifi
  • Pets Allowed

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
February 2018
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$734 /nt
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March 2018
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April 2018
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May 2018
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June 2018
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July 2018
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August 2018
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September 2018
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October 2018
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November 2018
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December 2018
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January 2019
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February 2019
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March 2019
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April 2019
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Reviews

Labor Day Weekend

Reviewed on 2017-09-06 by Jena M. from Philadelphia, PA
Visited September 2017
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The rental experience at Tradewinds was better than I imagined. We even got to check-in a couple hours early which was great since we traveled far by car. We were able to park the cars in the driveway and unload our stuff. The houses were perfect for two separate families on vacation together. It gave us the ability to have our own space but still be close. The houses were right off Duval street in the center of all the fun. They were clean and spacious with king size beds. The backyards were great to relax and unwind in the hot tubs. We throughly enjoyed our stay at the Tradewind houses.

Good location

Reviewed on 2017-08-09 by Recent Guest
Visited August 2017
4
Services from rental manager
2
Cleanliness
5
Location
4
Property condition
4
The cottages were very nice and location is great for duval street,we walked everywhere. Only issue is they refused to let us check in early so we waited outside for three hours until the door was unlocked , in the two hours that we waited there was no one inside cleaning so it appeared they just didn't let us check in for no reason -so we sat in the heat waiting. When I asked the lady about early check in she was acted irritated and was not friendly at all considering we paid almost $2000.00 for a two night stay ..I would expect more friendly staff when you rent a vacation place. There was also one roll of toilet paper for 6 women, found some in the other cottage.

Weekend Getaway

Reviewed on 2017-06-14 by Recent Guest from Cary, NC
Visited May 2017
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Great Memorial Day Weekend Getaway!!!

A girl's weekend

Reviewed on 2017-06-14 by Justina C. from Orlando, FL
Visited June 2017
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Fabulous rental property! Great location! It was the perfect size for our group of 10 and staff was friendly, helpful and professional and kept it clean.

Awesome

Reviewed on 2017-05-13 by Sharon P. from Coatesville, PA
Visited May 2017
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Our stay at the Tradewinds exceeded our expectations!! The homes were in a perfect location. Amentities were great! Would definitely stay here again. The only down fall was the hot tubs were not clean so we did not enjoy that part or our stay as we hoped to.

Chinn Family Thanksgiving

Reviewed on 2016-12-01 by Stephen C. from Merritt Island, FL
Visited November 2016
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5
All good - great facility and a great time had by all

It Worked For Us . . .

Reviewed on 2016-09-27 by Melissa J. from Naples, FL
Visited September 2016
4
Services from rental manager
4
Cleanliness
4
Location
4
Property condition
3
Biggest plus was the private parking (easily fit 4 vehicles). Beds were very comfortable. Location was good in conjunction with proximity to Duval Street. Housekeeping did what they said they would do. Hot tubs were in working condition. Drawbacks: One of the houses (Leeward) needs some landscaping trimming in the backyard. Both homes need some TLC (i.e. floors and walls could be redone due to peeling/scraping in many spots; appliances had rust on sides). Houses outside could be touch up painted and power-washed. Overall, these are minor issues that did not affect us.

Great little home for a couple or two

Reviewed on 2016-08-25 by Recent Guest from Woodbridge, VA
Visited August 2016
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The rental company was great and the homes were exactly as described. We rented both of the sister homes and lived it. Thanks.

Great place for large group!

Reviewed on 2016-07-13 by Jessica C. from Jacksonville Beach, FL
Visited July 2016
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4
We had a great stay with 10 girls in both of the Tradewinds houses. It was nice to be able to split up and have room to move around instead of 1 bigger house for all of us. There was plenty of space to have 5-6 girls in each house. Plenty of mirrors to get ready in! It was a good location, a short walk to everything, but far enough to not hear noise constantly. Overall, I would recommend for a large group!

Great place for a large group!

Reviewed on 2016-06-23 by Recent Guest from Mt. Juliet, TN
Visited June 2016
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
These places were a great place to gather with a large group. The homes comfortably slept 4 in each house but with the pullout bed, 6 people in each home was a tight squeeze. But you can't beat the location and the coziness of the places. Clean and inviting homes with some small maintenance issues that could be addressed to make the experience a little better, but nothing that overshadowed the stay. I would rent these places again when I go back to EYW.

30th Birthday Bash

Reviewed on 2016-05-23 by Rebecca K. from Waldorf, MD
Visited May 2016
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Our stay was great! Location was perfect and close to everything. Only called maintenance to fix the lock on the bathroom door. Everyone in my party enjoyed their stay as well. Complete success!

PERFECT PERFECT PERFECT

Reviewed on 2015-12-14 by Patricia G. from Upper Chichester, PA
Visited December 2015
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Only stayed for one night on a mini trip to Key West after a Caribbean Cruise. How nice that the rental agency did not have a minimum stay at these fantastic houses. They were perfect in every aspect. Location was phenomenal, houses were decorated beautifully and the beds gave us the best night's sleep during our entire vacation. Very sad we stayed just one night but do plan to rent the same houses when we return to Key West for a longer vacation. Rick at Key West Vacation Rentals was awesome. Very kind and accommodating. Allowed us to park our cars in his parking lot after we checked out so we could sightsee. Very impressed by entire experience. Highly recommend.

Great for a group staying together

Reviewed on 2015-12-09 by Dan C. from Manhattan Beach, CA
Visited November 2015
4
Services from rental manager
5
Cleanliness
4
Location
4
Property condition
5
Overall great location within walking distance to most everything, clean, nice, and comfortable. My only concern with the property is noise - you can hear pretty much everything that goes on outside, which begins to have you question some of the neighborhood late at night - not for the light sleeper!<br/><br/>Overall really a fantastic spot and perfect for the group staying together for the wedding we attended. The place is represented well in the pictures, and I would be happy to go back and stay there again!

Fun with Freinds in Key West

Reviewed on 2015-10-25 by Recent Guest from Tomball, TX
Visited October 2015
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3
A group of 4 couples stayed 5 nights in the Windward and Leeward houses. The houses are older and had a couple of maintenance issues but these were addressed promptly. These are not luxury accommodation, but the location is excellent and they were perfect for our group.

Girls Key West Trip

Reviewed on 2015-09-23 by Carla W. from Sussex, NJ
Visited August 2015
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4
The houses were just wonderful. Location was great.The only complaint I have is they need to replace the pull out sofas. The mattress were horrible.They advertise the houses to sleep 6 to a house. The bedrooms beds were very comfortable.OVERALL I GIVE THESE HOUSES A 8. If they replace the sofas I would give them a 9.

Tradewinds review

Reviewed on 2015-09-23 by Recent Guest from Pompano Beach, FL
Visited September 2015
4
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
4
Awesome!

Our family trip for my daughters wedding

Reviewed on 2015-09-16 by Francine L. from Niles, OH
Visited September 2015
4
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
3
The house was nice. great location.but we did have a problem with ants, in the kitchen all over the counter tops.

Ultimate vacation rental

Reviewed on 2015-08-13 by Marilyn M. from Miami, fl
Visited July 2015
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We could not ask for anything more perfect. Great house great location and wonderful concierge service. We always come back to rent through your company.

Great location!

Reviewed on 2015-08-08 by Amanda N. from Jacksonville, Florida
Visited July 2015
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
This place was extremely close to everything you would want to do in Key West! We had both houses for 10 girl and it was perfect! We all had our own areas to get ready and we were walking distance to everything! They brought extra towels every day and if you called they would bring extra linens. We had a great stay and would stay here again!

4th of July weekend at Tradewinds Group

Reviewed on 2015-07-09 by Michele S. from Pompano Beach, FL
Visited July 2015
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4
We booked both units for a group of 12 for 4th of July weekend. We were pleasantly surprised to see how much parking we had between the 2 cottages because it was a major concern of ours. We got all 4 cars in with room to spare. The Leeward cottage's kitchen was a lot smaller than Windward but it was fine because we all congregated in Windward for get togethers. The 4 bedrooms were ample in size and comfortable. Loved the wide, long hallways to store large items! The bathrooms were also good sized which helped with such a large group. The only negative comment I can think of was that the floors were not clean as well as the area rug. If you walked barefoot, your feet were black. The sofas could also use a cleaning. We all really enjoyed the location and the charm of these 2 cottages and I would highly recommend for a large group like ours. I would rent one or both of these again for sure.

Fun time in KW

Reviewed on 2015-06-07 by Edward G. from Raeford, NC
Visited May 2015
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Great vacation! Perfect accommodations and location.

Great Time

Reviewed on 2015-06-02 by Recent Guest from Bristol, WI
Visited May 2015
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4
We had a Great time and the rentals were clean, organized and homey!

Guy trip for 50th birthday- great property

Reviewed on 2015-05-29 by david b. from Conway, NH
Visited May 2015
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3
Great property. Very convenient. Close to everything. Beds were amazing comfortable. We had 6 guys for 5 days and would highly recommend. The property. Two things that they could improve on...Bathrooms need to be updated and the pull out couches are not comfortable at is the uncomfortable bar in the middle of your back......

Reasonably priced place to stay in Key West

Reviewed on 2015-05-23 by John B. from Kingsville, MD
Visited May 2015
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Location of property was very close to Duval St. and all of the local activities. King sized beds were very comfortable, and room space was adequate. Shrubbery around hot tub could use some trimming, and there were some minor maintenance issues in the bathroom and kitchen. Bedroom was lacking a closet and dresser for storing clothes, and the safe didn't work. But overall the stay here was very nice.

Very nice place

Reviewed on 2015-05-11 by Josh S. from Union City, OH
Visited May 2015
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4
Very nice place for the money close to duval street

Family Vacation

Reviewed on 2015-04-07 by Tom C. from Newburyport, MA
Visited March 2015
4
Services from rental manager
4
Cleanliness
4
Location
2
Property condition
4
We had a great time. Houses were clean and well maintained with the exception of a loose bedroom door knob. Downside is the location being across from the Monkey bar. Noisy at night until 3:00 AM...spring break week

Great place to stay with a large group!

Reviewed on 2015-01-24 by Recent Guest from Ashburn, VA
Visited January 2015
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
2 homes close together, hot tub in each backyard, grill and patio in each backyard, 4 bedrooms and 2 sofa beds, 1.5 blocks from Duval, easy to deal with staff makes it a highly recommended place to stay.

Key West Nov 13 - Nov 18

Reviewed on 2014-11-21 by Jason C. from Shelton, CT
Visited November 2014
4
Services from rental manager
5
Cleanliness
5
Location
3
Property condition
4
Overall, a very nice place to stay. While our group rented both villas, I will only speak to the Leeward as its where I slept. In our house, the bedrooms have slats and not windows; therefore, sounds from the street come in to the front bedroom. At times, it could be rather noisy. While I am a Red Sox fan, "Sweet Caroline" at 3:45am from the karaoke across the street was a bit unnerving. I will say that it was not every night of the trip, but only one. The strange thing was that the back bedroom was as quiet as a tomb and the residents had to turn on the TV for background noise to sleep. All in all, everything was in good order in the home with clean towels every day and comfortable beds. The two king beds were quite different, but very comfortable. The front bed was more plush while the back bed was firm. The hot tub was clean and perfectly functioning. The internet, on the other hand, could be spotty. The proximity to the nightlife was a quite a plus with most attractions within walking distance. The neighbors were friendly and extremely helpful. At checkout, I provided a list of nits to management. They took notes and appeared to want to fix any issues. In short, I would rent the villas again on a return trip, but maybe take the back bedroom instead.

The Best of Key West

Reviewed on 2014-10-30 by Christy R. from mesa, AZ
Visited October 2014
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We were a group of 7 people leasing these 2 cottage homes.The location could not have been better only 1 block off Duval St within walking distance to everything. The homes were clean , and fully equipped. We had trouble with a TV in one of the homes and the rental staff came quickly the next day and switched it out for a brand new TV. The cleaning staff came daily to make beds and add towels. We had a terrific stay in Key West and will definitely be back to lease these great cottage homes.

Keywest vacation rentals stay in 3 nights

Reviewed on 2014-09-20 by Robert G. from Olmsted Falls, OH
Visited September 2014
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Loved the property's and location. Very well maintained and stock. The two pools around the corner are awesome. I definitely would recommend them for your next vacation stay.

Wonderful home(s), Fantastic Experience!!

Reviewed on 2014-09-14 by Recent Guest from Tampa, FL
Visited September 2014
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Beautiful home away from home - all the comforts of home, well stocked kitchen, clean and roomy! We were here with a group of friends who had traveled from all over, and we were delighted to have such a friendly, comfortable, personable space to call home! *Perfect* location, both off the beaten path but right in the middle of it all! We could not have been happier!!

Great stay at the Tradewinds!

Reviewed on 2014-09-08 by Tim W. from Aldie, VA
Visited August 2014
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The Tradewinds was an excellent property! It was a short walk from Duval Street and all of the bars. The daily maid service cleaned up the house and also made the beds. We would definitely consider coming back!

Bachelorette Party

Reviewed on 2014-06-12 by Jennifer J. from Chicago, IL
Visited June 2014
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We had a great time! Plenty of space for everyone, clean houses, convenient location, awesome concierge, and a wonderful place to visit! I can't think of a single thing I would have changed!

GREAT PLACE in KW!

Reviewed on 2014-04-17 by Recent Guest from Worcester, MA
Visited March 2014
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The Tradewinds cottages were the perfect place for the 6 of us to stay in Key West. Location, location, location! Superb! Walked to many places. But also had off street parking! Delightful housing, took advantage of everything there. Loved the neighborhood and porches. Even though was "spring break" we were never bothered by any noise. Close to everything important to us!!!

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