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.

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

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

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!)

Yup, all rooms are spacious with Sweet Sleeper beds as deliciously comfortable as they sound.

Free parking means you're not stuck tracking down a spot.

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

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

Relaxingly retro for a good ol' beachy days vibe.

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

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

Practice your best Phelps impression at the pool.

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

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

Nicknamed the intriguing (though redundant) ‘hidden hideaway of the Florida Keys,’ this place is on 6 blissful acres of private sugar sand beach.

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

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.

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

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

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

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

Courtyard pool confirms you have indeed arrived in Key West, lined with palms and loungers.

Strolling distance to plenty of great bars, restaurants, and luxury shopping (if you're feelin' bougie).

Fittingly located in Miami's ultra-hip design district.

Get some feng shui in your stay – rooms are designed to max the flow and natural light.

Early flight? Sometimes it just makes more sense to stay close to the airport. Unless you like running with luggage. Your call.