The Oriole Key West

106 Simington St, Key West, FL 33040

Tucked away in the quieter corners of Key West’s Old Town streets sits The Oriole Bar—a small, dimly-lit hideaway perfect for escaping the tourist hustle. Known by locals as a laid-back haven, it offers an unpretentious, authentic Late Night atmosphere with affordable drinks served cash-only, ensuring simplicity and ease.

Inside, The Oriole Bar feels comfortably cozy, its worn wooden interiors and soft lighting offering a welcoming, low-key vibe. Vintage signs and local memorabilia subtly decorate the walls, adding understated character without distraction. Conversations flow quietly at the bar, mingling easily with the occasional clack of billiard balls coming from the solitary pool table tucked into a corner—an inviting diversion for patrons seeking a friendly match or a casual pastime, until the music starts thumping for some late night fun.

Behind the simple bar setup, bartenders serve straightforward, budget-friendly drinks—from ice-cold domestic beers to classic pours, offering refreshment without breaking the bank. Regulars gather around, chatting effortlessly, appreciating a spot where familiar faces and a relaxed atmosphere are guaranteed.

At The Oriole Bar, it’s all about authenticity and relaxation—a modest getaway spot where locals retreat and visitors feel genuinely at ease, far from the noise and crowds, savoring the quiet charm and easygoing rhythm of real Key West.