Marriott Key Largo Bay Beach Resort Rating: 4.0 Pearls
This 153-room property is located in northern Key Largo, a short drive from the John Pennekamp Coral Reef State Park, and close to shops and restaurants. Not a lot stands out, but there are a few perks -- like a diver’s center on-site, an adequate spa, and a nice private beach (albeit a tiny one). Big rooms have flat-screen TVs, free Wi-Fi, and nicer decor than other mid-range chains in the area. Book a room with an ocean view to enjoy the beautiful Key Largo sunsets.
Sunset Key Guest Cottages, a Westin Resort Rating: 4.5 Pearls
This 40-room resort caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities. It is located on Sunset Key, a residential island off Key West, and is affiliated to the Westin Key West, with which it shares some features, such as the fitness center and the restaurants. The hotel itself has wonderful amenities, including a lovely pool, a gorgeous beach with palm trees and clear waters, and a pleasant spa. Its location, though idyllic and exclusive, might be somewhat inconvenient for travelers who want to be close to shops and restaurants (the hotel only has one eatery on-site).
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 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, but the hotel's private white-sand beach with a pier for fishing is just as nice.
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.