5 Dream Adventures In Key West

Cloud 9 pool

While most everywhere else is making preparations to winter up and hibernate until the spring thaw, Key West continues to be sunny and warm with breathtaking sites that draw crowds every night for the sunsets, arts, recreation and culinary spectaculars. Our Conch Republic is one of the most beautiful places in the world. It's also where you'll enjoy these five dream adventures in Key West. 

Live Music At The Green Parrot 

The Green Parrot Bar is an iconic Key West saloon with dive bar credibility where locals come to kick back, enjoy a drink or two and jam to great live music. Set in a 100-year-old building that was once a grocery store, the Green Parrot Bar on Whitehead Street is one of the most consistently popular bars in Key West and was named one of the top bars in America by Playboy Magazine and one of the top live music venues in Florida by The Guardian. Where To Stay: Cloud 9 - Nightly Rental

The Ernest Hemingway House

"Papa" and his then-wife Pauline fell in love with Key West and this is where he finished his semi-autobiographical novel A Farewell To Arms. Their charming home is now a major tourist attraction that lovingly presents his eclectic collection of furniture, art and collectibles from his worldly travels. The descendants of his beloved polydactyl cats still roam the estate. Where To Stay: Dreaming on Duval - Nightly Rental

The Red Barn Theater

Take in a show at Key West's longest-running professional theatre. In 1980, a spirited group of actors and technicians renovated the theatre, opening the doors of the Red Barn TheatreThey have been producing plays in paradise for the past 32 years. Where To Stay: The Truman Suites - Nightly Group Rental

Old Town Literary Walking Tour

Stroll through downtown Key West and be regaled with illuminating stories of writers that have called Key West home. Inspired by David A. Kaufelt’s original literary walking tour, this new tour features the former homes and favorite haunts of writers, including Tennessee Williams, Shel Silverstein, Elizabeth Bishop, and Robert Frost, and highlights tales of our lesser-known local talent. Where To Stay: Villa Luxe - Nightly Rental

Bo's Fish Wagon

You don't need to dust the sand off your feet to eat right in this town. For the perfect fish sandwich, head to B.O.'s Fish Wagon . It's a hopping little open-air shack that turns out fresh food with zero fuss, as well as great live music on Friday nights. Don't miss the cracked conch sandwich ($12), tiny strips of fried conch stuffed between fresh Cuban bread and shot with Key Lime mayo. Where To Stay: Butterfly Cottage - - NEW Nightly Rental    

Sunset Celebrations At Mallory Square

When you vacation at the southernmost end of the United States you'll want to mark the occasion with something truly spectacular. The Mallory Square sunset celebration is the perfect place to sit and relax, sip evening cocktails and enjoy one of the most breathtaking sunsets you'll ever see. As the sun sets over the Gulf of Mexico, watchers hold their breath in anticipation of seeing a rare and beautiful sight as the sun vanishes over the horizon, the famous “green flash." Just as spectacular are the performers, artists and an assortment of food vendors assembling to ensure that your evening is unforgettable. Where To Stay: Seas The Day! - Weekly Rental    

These are five of our favorite dream adventures in Key West and there are plenty more we'd love to tell you about.  Reserve your favorite luxury boutique rental from our collection and start making plans for your favorite Key West dream adventures!