Casa Marina, A Waldorf Astoria Resort

Many of Key West's best hotels are clustered around Mallory Square – but this landmark property (which is listed on the National Register of Historic Places) bucks that trend with its Reynolds Street address by the Atlantic Ocean. Guests, however, are enthralled by more than its historic ambience and away-from-the-crowd locale. Although some guests say accommodations here are a bit small, they are still outfitted with modern amenities like espresso machines, iHome docking stations and flat-screen TVs. Along with the comfy lodgings, Casa Marina, A Waldorf Astoria Resort also boasts access to Key West's largest private beach and the Spa al Mare, which offfers a wide array of services, including seaweed detoxifying body wraps and beachside massages. And the two outdoor pools overlooking the ocean have been described as nothing short of amazing by sun-seeking guests. A stay at this Waldorf Astoria outpost can be pricey, but if you're a Hilton Honors member, you can accrue or cash in points by choosing to bed down here.