Pineapple Bar
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Pineapple Bar
Tucked in Historic Old Town on Key West's serene Atlantic Coast lies an oasis in the middle of the party. A short walk from the eclectic shops, famed nightlife, and signature architecture of Duval Street, the Southernmost Beach Resort offers an island retreat away from the hustle and bustle.

Where tradition meets modern luxury, you'll find lush garden pathways, endless sea views, sandy beaches, and us-on this quaint stretch of America's Southernmost point.The Southernmost Beach Resort welcomes guests of all abilities. Our property descriptions aim to allow any visitor to make an informed decision on whether the hotel is an appropriate choice for their needs.
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Modern design meets romantic setting in each one of Southernmost's stunning accommodations. From palm-fringed pool views in the middle of the action to intimate seaside retreats with premier guest services, you'll find casual luxury and a warm island welcome wherever you decide to stay with us. Please note that our rooms are ADA compliant under the Department of Justice ADA Title III Regulation 28 CFR Part 36, 1991.
Formerly known as The Avalon and Duval Gardens, these guesthouses blend history with contemporary coastal decor. Take in the magical atmosphere of Key West from the guest room of an elegantly restored, turn-of-the-century Victorian home. Located on Historic Duval Street, The Avalon is a historic 19 room home with origins dating back to 1885.
Fresh flavors from the boat to your table. Southernmost serves up island cuisine with a unique twist. Just 90 miles from Cuba, you can indulge in dishes equally inspired by our Caribbean neighbors, as well as classic Americana and Asian-fusion. Listen to live-music poolside with a cocktail in hand while diving into grilled flatbreads.
Fortune 500, small business, or family-we have a space for you and your next celebration. Many spaces in fact. Six acres of resort are set on the Atlantic Ocean with four bars and four meeting spaces. Whether an indoor or outdoor event, we're ready to accommodate parties of 25 to 200. Three relaxing heated-pools, two white sand beaches, and hundreds of places to stay.
Warm tropical breezes. Rolling ocean vistas. A kiss to seal it all under a hazy, pink sunset. Here, enjoy an intimate island experience, no matter how large the celebration. Four romantic venues offer premium amenities and flexible spaces to host your special day (or week) the way you've always imagined it.
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