This charming little cottage is situated in the centre of Key West's Old Town, on the island's highest point. With its teal shutters and cute covered porch, you can easily imagine this home tucked away in Cuba's verdant Viñales Valley. In addition to its prime location, everything about this award-winning historic home is designed to enhance the relaxed, barefoot beachy vibes of Key West. There are wooden floors underfoot inside and out, which helps blur the lines between them – aided by the balmy subtropical climate. The tranquil bedrooms keep things relaxing with neutral tones and natural materials to help you wind down before bed. There's also a comfortable living area and an adjoining sitting room, with a door that can separate the two for a bit of privacy. The kitchen has everything you could need for family feasts, which are, of course, best enjoyed outdoors on the poolside decking. There are a couple of loungers out here to make the most of the Florida sun and a pool with oversized steps and a vast waterfall wall that'll make you feel like you're in a Radox ad. In the evening, you should make sure to pick up some authentic key lime pie and continue to Mallory Square for sunset and a slice.

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