Hawks Cay Resort Rating: 4.5 Pearls
Hawks Cay Resort has the feel of a small village, due to its massive size and many amenities -- the property even has its own 85-slip marina. Many guests arrive by boat, as the resort is located on Duck Key, a secluded spot far from Key West's main airport. The property largely attracts families looking for a quiet vacation, thanks in part to family-friendly features such as a dolphin experience, kids' club, and multi-bedroom villas. But its numerous on-site amenities and large rooms make it a great pick for business travelers as well. With 20,000 square feet of oceanfront meeting space (more than anywhere else in the Keys), the resort also features business-friendly amenities including a spacious fitness center, numerous dining options, and free Wi-Fi and parking.
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 and though the hotel is decidedly romantic, it is a great choice for business travelers as well. Not only does it boast one of the only golf courses on the keys (a 9-hole Jack Nicklaus-designed 3-par), but it also features great on-site dining, spacious rooms, and plenty of indoor and outdoor meeting space.
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. Other business-friendly amenities include top-notch restaurants, more than 22,000 square feet of meeting space, a business center, and shuttle services to the airport and nearby hot spots.
The Reach, a Waldorf Astoria Resort Rating: 4.0 Pearls
The Reach offers respite from rowdy, gaudy Key West with its brand of relaxed sophistication and its beachfront location. Its 150 rooms are what you would expect from the Waldorf Astoria crowd: spacious, modern and clean, with generic high-end furnishings and comfortable beds outfitted in crisp linens. They feel just a tad less upscale than those at the Casa Marina, its sister hotel next door (partly due to the use of carpet, rather than Casa Marina's tile or wood), but the hotel's private white-sand beach with a pier for fishing is just as nice. It also offers several meeting rooms, a business center with secretarial services, and a tasty steakhouse which has a private dining room for events.
The Westin Key West Resort & Marina Rating: 4.0 Pearls
This 178-room waterfront hotel in Old Town Key West is a real resort, with dozens of features, including boat rentals, shops, a fitness center, and a marina. However, it's not quite up to the standards of other Westin properties, with somewhat bare contemporary rooms, cramped bathrooms, a pool that's a bit small for the size of the hotel, and a location right by a busy and noisy cruise ship dock. Nonetheless, it is a business-friendly property with amenities such as 16,000 square feet of indoor/outdoor meeting space, a business center, and free Wi-Fi. Its three on-site restaurants and location in Old Town Key West also make it a convenient option.