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Ideal for: Beach Lovers, Outdoor Enthusiasts, History Buffs
The southernmost point in the continental United States, Key West sits roughly 90 miles north of Cuba. This laid-back, quirky island is known for its pastel-hued, conch-style houses and colorful coral reefs popular among diving and snorkeling enthusiasts.
Located just 500 yards off of Key West, the 40 cottages comprising Sunset Key Cottages are situated on their own private island escape with easy access to everything Key West has to offer.
Key West is a tropical island city and the westernmost point of the Florida Keys archipelago. More than just key lime pie, this secluded destination is famous for its year-round sunshine, laid-back lifestyle, and historic sites. It is also home to the largest coral reef in North America (and third largest in the world). Snorkel, paddle, sail, and fish the crystal-clear waters where the Atlantic Ocean meets the Gulf of Mexico. Back on land, visit one of the most photographed places on the Key West—a colorful, oversized concrete buoy marking the Southernmost Point in the U.S. From there, travel the lively Duval Street to Mallory Square to take part in a nightly sunset celebration, which truly embodies the fun and funky spirit of this small piece of paradise.
Explore the prize-winning author’s former home located in the heart of Old Town. Keep an eye out for the famous six-toed cats that roam the unique property, now a U.S. National Historic Landmark. Afterwards, head to Hemmingway’s favorite Key West hangout, Pepe’s Café.
With only eight square miles of total land area, cruising around Key West on a bicycle is not only easy, it’s one of the best ways to explore the island’s many beautiful beaches and popular sites such as the Historic Seaport, Mallory Square, and the Key West Lighthouse.
This lively mile-long stretch from Mallory Square to the Southernmost Point is lined with quirky restaurants, boutiques, art galleries, dive bars, and saloons. Do a pub crawl or grab a seat at an outdoor cafe to enjoy some live music and people-watching.
Lying roughly 90 miles north of Cuba, Key West enjoys a comfortable year-round climate similar to that of the Caribbean. With air and water temperatures typically holding steady between 73°F and 83°F all year long, Key West is a perfect vacation destination in any season, although August is usually the hottest month while is January is the coldest. The Florida Keys have largely escaped effects of the annual Atlantic hurricane season, but still tend to see the most annual rain from June through the end of autumn.
Google Maps satellite images are not always up-to-date, especially in non-U.S. destinations. Some Inspirato accommodations are located in developments built after images were last updated. Our pin placements represent our best location estimates, but actual locations may vary.