Casa Marina Resort - a Waldorf Astoria Resort Rating: 4.5 Pearls
The 311 rooms of the Casa Marina Resort have a light, sophisticated, but still island-y feel, with neutral tones, sheer curtains, and sleek hardwood or tiled floors. The resort also offers great in-room amenities, including free Wi-Fi, flat-screen TVs, and espresso machines. Although bathrooms aren't anything grand (just simple walk-in showers or shower/tub combos), they're clean and sleek. The resort's grounds are beautiful, with palm trees and lush foliage, and lead to a rare amenity in Key West -- a swimmable beach. Although it's too rocky to wade into the water, a long dock extends to sandier bottoms. The hotel first opened in 1920 and was designed by the same architects that built New York's Metropolitan Opera House and the New York Public Library.
Cheeca Lodge & Spa Rating: 4.5 Pearls
The 114-room Cheeca Lodge was one of the original luxury properties on Islamorada, dating to 1946 and earning plenty of celebrity cachet over the years (high-profile guests have included George W. Bush). The property was rebuilt after a fire gutted its main building in 2009, and now has bright, spacious rooms with tropical-luxe decor and massive bathrooms. The lush grounds are especially pretty at night, with Tiki-torch-lit paths. But the hotel's beach is manmade -- there's even a rock ledge on the water's edge -- making it muddy at times and less than ideal for swimmers and waders. And the family pool can get crowded; those traveling without children will probably prefer the much calmer adult-only pool.
The Weatherstation Inn Rating: 3.5 Pearls
This charming, 8-room property is housed in a historic building on a quiet street in Old Town Key West, within walking distance to some of the major tourist attractions, and to a couple of good beaches. Each of its rooms has a distinct character and few amenities (a flat-screen TV and little more), but they come with charming decor (four-poster beds, antique touches) and relaxing views of the well-tended grounds. The hotel has no amenities whatsoever -- just a tiny pool -- but there are some great freebies like free Wi-Fi, free parking, and a free quality continental breakfast.
Marquesa Hotel Rating: 4.0 Pearls
Refurbished from 1884 conch houses, the Marquesa Hotel is a compound of four buildings surrounding lovely interior gardens and two pools. A narrow staircase off the lobby leads to the individually decorated rooms. Light and airy rooms feature flat-screen TVs, mini-fridges, and cozy sitting areas with ottomans. Bathrooms are basic and clean with shower/tub combos and marble sinks. Suites have private terraces with cute wicker furniture and some are adjacent to one of the hotel's pools. An appealing on-site restaurant, Cafe Marquesa, serves fresh local seafood. No children under 14 are allowed at the hotel, providing this property with a distinctly romantic feel. Free Wi-Fi and parking add value, and the Old Town location two blocks from Duval Street is convenient.
Crowne Plaza Hotel Key West - La Concha Rating: 3.5 Pearls
The Crowne Plaza is a National Historic Landmark dating to 1926, but today this mid-range chain is well past its prime, and lacks the charm of other historic hotels, like The Weatherstation Inn. The whole property is showing a bit of wear, and the 160 rooms are compact and frill-free (though white wicker chairs and honeycomb-tile bathroom floors do provide some classic charm). The best feature is, without a doubt, the location on lively Duval Street -- the main artery of Old Town Key West, lined with restaurants, shops, and bars. (It's a good 15-minute walk to the beach, though.) The rooftop deck is another highlight, with beautiful views of the ocean and the tops of palm trees dotting the landscape.
Eden House Rating: 3.0 Pearls
Eden House has had the same owner for nearly 40 years, and numerous loyal customers return year after year for the affordable prices and friendly vibe. Rooms can be bare-bones, especially the semi-private ones with shared bathrooms and no TVs or mini-fridges. Even the higher-level rooms are fairly plain, though, with small bathrooms, simple (verging on bland) decor, and very little furniture (aside from the apartment-style rooms). This historic hotel does have a nice pool courtyard surrounded by palm trees, lovely grounds with deck areas, hammocks, and koi ponds throughout, and tons of freebies (Wi-Fi, parking, and happy hour) that make it a good value.
The Banyan Resort Rating: 3.0 Pearls
Key West is a place that's steeped in history, and the Banyan Resort is no exception: Its nine buildings are on the National Register of Historic Places. The 38 suites are clean and bright, but quality varies drastically. Most have dated, uninspired decor, with tube TVs, floral print sofas, and tacky lighting. But each suite has patios, balconies, and kitchens; the grounds are lush; and there are two shady (if small) outdoor pools. The hotel's biggest draw is its location just steps some of Key West's premier attractions, such as happening Duval Street and Mallory Square.