64 Best Hotels in The Florida Keys, Florida

A small world all its own, this adults-only maze of accommodations and four swimming pools makes you feel deliciously sequestered from Key West's crasser side but keeps you close enough to get there on foot. The "basic" rooms are in an old cigar factory, and each has its own unique decor (and street noise). There's also a restored shotgun house, cottages, and a town house. An over-the-top continental breakfast is served on the brick-paved courtyard.

Operated by the same company as the ultra-high-end Santa Maria Suites, this motel-style property is a good-value option in pricey Key West. Though some rooms have been updated with dark-wood furnishings, others still have older, white-wicker pieces. All, however, have 32-inch flat-screen TVs, and those with kitchenettes are spacious, with high ceilings and dining-sitting areas. Key West's famous South Beach and the Southernmost Point are just a few minutes' walk, and you'll find three pools on-site to keep you cool. If you're a light sleeper, the roosters may be a bother, but that's just part of Key West's charms. A modest resort fee gets you a simple breakfast and a voucher for a beach chair and umbrella at nearby South Beach.

During Prohibition, Raul Vasquez made this place popular by smuggling in rum from Cuba; today, its reputation is for having reasonably priced rooms within walking distance of the beach. Of course, the booze is legal now, and there's a bar in the lobby offering 350 brands of rum. Accommodations have kitchenettes that include a refrigerator, microwave, kitchen sink—everything you need. Pastel-painted walls are accented by bursts of color in rugs, pillows, and seat cushions. The rooms are basic, but some have nice touches like claw-foot tubs. Room 1A has a balcony that's good for people-watching.

Part of the Kimpton Hotel brand, this 1854, Grand Bahama–style house on the National Register of Historic Places is in the center of Key West, just two blocks off Duval Street, and features vibrant gardens, three private pools, and an outdoor bar. In true Kimpton fashion, the hotel is pet-friendly, and has lots of amenities, including complimentary Continental breakfast, yoga mats and Turkish robes in every guest room, and snorkel kits to use at the beach and island snorkeling spots.