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Tradewinds

Available Rentals

Tradewinds

4 Bedrooms
2 Bathrooms
4.7352941176471
(34 Reviews)
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...

Leeward Isle

2 Bedrooms
1 Bathroom
4.76
(25 Reviews)
One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,...

Windward Isle

2 Bedrooms
1 Bathroom
4.6
(35 Reviews)
One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design.

The Webster Dictionary dates windward back to 1549; defined as, the side or...