Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.

Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.

Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.

Quaint and quiet historic ‘hood, but an easy 8-min stroll to the world-famous dining/nightlife action on Duval Street.

Newly reimagined! Amazing location on the gorgeous beach – fitting that this spot is owned by an artist.

Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.

All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.

Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.

Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.

You know what’s nice to wake up to? Free breakfast, that’s what.

On a private stretch of sand overlooking the bay, plus a pool with views, swimming lagoon and fishing pier.

Maxin’ & relaxin’ by the canal (right outside!) is how we love to end our day.

The hotel has its own private island, complete with a pool, secluded cabana, bar and, of course, stunning views.

Steps from Duval Street as well as the ocean, it's a perfect little motel in all its aquamarine glory.

Inviting residential setting puts you less than a half-hour from Key West and Marathon if you’re up for exploring. (But first, free breakfast!)

Primping, preening, and pampering to the max with onsite spa services.

Gorgeous little getaway in Marathon with easy access to the bay and the ocean.

Awesome outdoor pool with plenty of space. Kick back with a drink from the poolside bar.

Jutting out into the water on a pier (surprise!), it has its very own slice of private beach.

Shopping, golfing, Everglades alligator spotting, Key Largo beaches – all nearby.

Stunning modern décor throughout. Living room rocks a sofa and wet bar for an awesome getaway.

Classic Key West digs boasting contemporary-tropical decor in the rooms juxtaposed with the original, historic facade just a block off Duval.

Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).

Unwind with a dip in the relaxing outdoor pool after the day's adventures.

Whatever time you stumble in, the 24-hour front desk serves up service with a smile.