Book by phone: +1 (305) 296-9292
Comprised of Two Cigar Makers Cottages, Tradewinds is Truly Unique.

Tradewinds - Nightly Group Unit

Guest Rating:

Vacation rental house. Sleeps 12, 4 bedrooms, 2 bathrooms. Cats, Dogs allowed.

529-531 Olivia St Key West, FL 33040 United States

view full size image gallery

  • Comprised of Two Cigar Makers Cottages, Tradewinds is Truly Unique.
  • This Jacuzzi Area Behind One of the Residences Affords You With Luxury and Privacy.
  • From Another vantage Point You Can Enjoy a Comfortable Seat While Taking in the Tropical Foliage
  • Each of the Cottages Has it's Own Appeal Which Draws You In.
  • The Second Jacuzzi Area Has the Same Style and Privacy.  In This Picture You can Also See One of the Group's Grills Which Provide For Great Outdoor Food Preparation.
  • King Size Bed Room With TV and Ceiling Fan.
  • A View From End to End of the Shotgun Style Home and It's Many Features Including a Stereo System For Your Entertainment and Enjoyment.
  • One of the Comfortably Furnished Front Porches Which Allows for Taking in the Sights Which This Area of Key West Has to Offer.
  • From the Porch You Have a Great View of the Beautiful Neighborhood.
  • Another of the King Sized Bed Rooms With Ceiling Fan, Air Conditioning and French Doors Where You Will Be Surrounded By Rich Wood Walls and Floors.
  • This King Bed Room Offers Ample Space and Light and Also Boasts the Wood Accoutrements of a Fine Conch Home.
  • This Comfortable Living Area in One of the Units Has a Queen Sleeper Sofa, Ceiling Fan, Flat Screen TV, and Bar Seating for the Connecting Kitchen.
  • Beautiful Living Room Area With Flat Screen TV
  • Fully Equipped Kitchen Area
  • View Through to the Front of the Home From the Fully Equipped Kitchen Area
  • Spacious Full Bathroom With Vanity With Hair Dryer For Your Convenience
  • View of Hallway Throughout the One Unit
  • Microwave and Small Appliances for Your Convenience
  • The Second of the Two Living Areas With a Sleeper Sofa, Ceiling Fan, Air Conditioning Unit, and Stylish Comfortable Furnishings.
  • Outdoor Space With Outdoor Shower, Jacuzzi, Grill, and Seating
  • Living Area With Flat Screen TV and Stereo System for Your Entertainment Pleasure
  • Living Area With Ample Seating
  • Living Room Facing the Kitchen and Bath Room Areas
  • King Sized Bed Room With Flat Screen TV, Ceiling Fan, land Air Conditioning Unit.
  • Bedroom Facing the Hallway
  • Bright and Airy Full Bathroom With Tub and Beautiful Mirror
  • Another View of One of the Beautiful Bathrooms With a Full Vanity.
  • Fully Equipped, Spacious Kitchen
  • A View from the Fully Equipped Kitchen Through to the Front of the Home
  • Tropically Landscaped Outdoor Space Featuring an Outdoor Shower
  • Fully Equipped Kitchen Area With Access to the Outdoor Spaces
  • Back Yard Access Including the Grill and Patio Area
  • Rental of this Unit Grants Access to Our Off-Site, Heated, Adults Only - 21 Years and Older - Pool and Lounger Area
  • Rental of this Unit Grants Access to Our Off-Site, Heated, Adults Only - 21 Years and Older - Pool and Deck Area
  • Rental of this Unit Grants Access to Our Off-Site Heated Community Family Pool and Deck Area
  • Rental of this Unit Grants Access to Our Off-Site Heated Community Family Pool and Lounger Area
Comprised of Two Cigar Makers Cottages, Tradewinds is Truly Unique.

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.

Download Vacation Rental Flyer
Rooms and Amenities
Property Type House, 1 story
Unit Code 531_TW
Beds 4 king beds, 2 queen beds
Bathrooms 2 bathrooms
Rooms Sleeps 12
Floor Area 1620 square feet
Pets Cats, Dogs allowed.
Living Air Conditioning, Ceiling Fans, Linens, Ironing Board, No Phone, Free Wifi
Kitchen Full Kitchen, Refrigerator, Coffee Maker, Microwave, Toaster, Cookware
Business Nearby ATM, Nearby Post Office, Nearby Internet Cafe, Nearby FedEx, Nearby Bank
Outdoor Deck, Patio, Gas Grill, Outdoor Shower, Hot Tub, Outside eating area, Off-Site Shared Pool
Geographic Near Beach, Close to Duval
Entertainment Cable TV
Average Manager Rating (Based on 1153 reviews)
Overall satisfaction: 4.5 stars
Overall satisfaction
Services from rental manager: 4.5 stars
Services from rental manager
Average Vacation Rental Rating (Based on 7 reviews)
Overall satisfaction: 5 stars
Overall satisfaction
Cleanliness: 5 stars
Cleanliness
Location: 4.5 stars
Location
Property condition: 5 stars
Property condition
100 % of our reviewers would recommend this vacation rental.

Vacation Rental Reviews

  • Key West Nov 13 - Nov 18

    Stayed 5 days in November, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 3
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 4

    Jason C from Shelton, CT recommends this vacation rental

    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

    Stayed 7 days in October, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Christine R from Mesa, AZ recommends this vacation rental

    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

    Stayed 3 days in September, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Robert G from Olmsted Falls, OH recommends this vacation rental

    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!!

    Stayed 3 days in September, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    a guest from Tampa, FL recommends this vacation rental

    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!

    Stayed 3 days in September, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Tim W from Aldie, VA recommends this vacation rental

    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

    Stayed 4 days in June, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Jennifer J from Chicago, IL recommends this vacation rental

    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!

    Stayed 6 days in March, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    a guest from Worcester, MA recommends this vacation rental

    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!!!

  •  
Getting your rate Getting your rate...
1. Select Your Dates to Check Availability

Click calendar to set checkin/checkout dates. clear calendar

 Unavailable  Selected  Available  Checkin only  Checkout only
2. Review Dates and Rates

Select/Confirm the number of travelers to get a rate quote.

: :
Base Rent:
Fees & Taxes:*
Total Price:
:
:

*Click 'Continue Booking' to view details of fees & taxes

Seasonal Rental Rates for this Vacation Rental

Dates Daily Weekly Monthly Minimum Stay Checkin Restrictions
Dec 12, 2014-Dec 23, 2014 $628-$678 $4,746 na 1 Sun, Mon, Tue, Thu, Fri, Sat checkin only
Dec 24, 2014-Jan 1, 2015 $828 $5,796 na 1 No restrictions
Jan 2, 2015-Apr 30, 2015 $628-$678 $4,746 $20,340 1 No restrictions
May 1, 2015-Jul 31, 2015 $538 $3,766 $16,140 3 No restrictions
Aug 1, 2015-Sep 17, 2015 $468 $3,276 $14,040 3 No restrictions
Sep 18, 2015-Sep 20, 2015 $538 na na 3 No restrictions
Sep 21, 2015-Oct 20, 2015 $468 $3,276 $14,040 3 No restrictions
Oct 23, 2015-Oct 31, 2015 na $6,146 na 7 No restrictions
Nov 1, 2015-Nov 30, 2015 $538 $3,766 $16,140 3 No restrictions
Dec 1, 2015-Dec 11, 2015 $468 $3,276 na 3 No restrictions
Dec 12, 2015-Dec 23, 2015 $678 $4,746 na 1 No restrictions

*Seasonal rates are estimates only. Actual rates may differ. Seasonal rates do not include fees or taxes.

To request information about booking this vacation rental, please fill out the form below.


Sorry, we encountered the following error(s):

  • Unable to process request.
loading Sending Email...
Your email has been sent successfully!

Sorry, we encountered the following error(s):

  • Unable to process request.
loading Sending Email...
Your email has been sent successfully!
24.552818,-81.798925
CALL US 1-(800) 797-8787

Key West Vacation Rentals 1075 Duval St Suite C22 Key West, Florida 33040 +1 (305) 296-9292 rick@hgakwvr.com

© 1999 - 2014 | Powered By Escapia Vacation Rental Software | Terms of Use

Logon