Heron House The three-building property is distinguished by artistic touches, such as stained-glass transom windows, intricately patterned brick patios, and acollection of rare orchids. The 23 rooms are large, with private decks and high ceilings; walls of teak or cedar marquetry add warmth. 512 Simonton St.; 800/294-1644 or 305/294-9227; www.heronhouse.com; doubles from $189.
Island City House Hotel This 24-room compound includesan 1880's mansion fronting the street whose 12 "parlorsuites" are decorated with Victorian antiques—somewhat dark for the Keys. The gingerbread-trimmed Arch House, over the old carriage entrance, has brighter interiors but simpler furnishings; rooms in the old cigar factory are larger, each with a hammock overlooking the pool. 411 William St.; 800/634-8230 or 305/294-5702; www.islandcityhouse.com; doubles from $210.
Lightbourn Inn A 1903 Queen Anne house on a busy street conceals an astonishing display of compulsive knickknackery: autographed pictures of movie stars; antique furniture, lamps, and objets from around the world; and an entire wall of teddy bears. Breakfast is served by the pool—on Fiestaware, of course. 907 Truman Ave.; 800/352-6011 or 305/296-5152; www.lightbourn.com; doubles from $178.
Marquesa Hotel When it opened in 1988, the Marquesa raised the bar among Key West hotels. The original building, a landmark 1884 Greek Revival boardinghouse, was bought by two local men who specialized in restoring Key West's architectural gems. They furnished the 27 rooms with iron four-posters, pine sleigh beds from Indonesia, English armoires, and planter's chairs from the Caribbean. The Marquesa's courtyard—two small pools surrounded by tropical plantings—is exquisite. Service is graciousness defined: a glass of white wine when you check in, a receptionist who remembers your name when you call six months later. Hands down, the best place to stay in Key West. 600 Fleming St.; 800/869-4631 or 305/292-1919; www.marquesa.com; doubles from $275.
Simonton Court The former cigar factory turned 26-room hotel is made up of several structures, including a Gothic Revival manse with mazelike staircases; a cigar maker's shotgun house; and Bahamian-style cottages. Some rooms have rather ordinary furnishings; those in the mansion and the town house are generally more inspired. 320 Simonton St.; 800/944-2687 or 305/294-6386; www.simontoncourt.com; doubles from $209.
KEY WEST RESORTS
There are several standouts among the island's larger properties. The 311-room Wyndham Casa Marina Resort (1500 Reynolds St.; 800/626-0777 or 305/296-3535; www.wyndham.com; doubles from $359), built by Henry Flagler in 1920, is reminiscent of other Florida land-boom hotels. The beautiful grounds slope down toward a large beach. A nearby sister property, the pink concrete Wyndham Reach Resort (1435 Simonton St.; 800/626-0777 or 305/296-5000; www.wyndham.com; doubles from $329), has a smaller beach and similar resort amenities; all 150 rooms have balconies. • The Pier House Resort & Caribbean Spa (1 Duval St.; 800/327-8340 or 305/296-4600; www.pierhouse.com; doubles from $290) established its reputation in the late sixties and has been coasting ever since. It's a large complex near Mallory Square with a popular beach and three restaurants. Rooms in the Caribbean Spa building are best. • The Hilton sits on the Old Town waterfront, but Sunset Key Guest Cottages (245 Front St.; 888/477-7786 or 305/292-5300; www.sunsetkeycottages.hilton.com; cottages from $485) is its ace in the hole: a semi-private island 10 minutes away by launch, with a beach, restaurant, bar, and 37 bungalows. • The 120-room Hyatt Key West Resort & Marina (601 Front St.; 800/554-9288 or 305/296-9900; www.hyatt.com; doubles from $325) is one of the smallest of the large resorts, and has a low-key feeling. • Smaller yet is Ocean Key Resort (No. 0 Duval St.; 800/328-9815 or 305/296-7701; www.oceankey.com; doubles from $399), founded by the owners of Little Palm Island, who bought a characterless building at the foot of Duval Street and sank $5.5 million—and a lot of bright paint—into it. Book a room overlooking Mallory Square: all you'll remember seeing is the sun dropping below the horizon.