A nearby sister property, the pink concrete Wyndham Beach Resort (1435 Simonton St.; 800/626-0777 or 305/296-5000; www.wyndham.com; doubles from $329, kids free), has a smaller beach and similar resort amenities; all 150 rooms have balconies.
The Hilton Key West Resort & Marina (245 Front St.; 888/477-7786 or 305/294-4000; www.hilton.com; doubles from $299) sits on the Old Town waterfront and is walking distance from shops, restaurants, and galleries. Spend a day (or week) at Sunset Key, the resort's 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. Bicycle and scooter rentals available.
Smaller yet is Ocean Key Resort (No. 0 Duval St.; 800/328-9815 or 305/296-7701; www.oceankey.com; doubles from $399, kids under 18 free), 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.
Island City House Hotel This 24-room compound includes an 1880's mansion fronting the street whose 12 "parlor suites" 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. This is one of the few small hotels in Key West that allows kids of all ages. The one-bedroom suites in the Island City House and Cigar House have sleeper-sofas in the living room and are ideal for families. There's a large pool, and cribs, high-chairs and strollers are available free of charge. 411 William St.; 800/634-8230 or 305/294-5702; www.islandcityhouse.com; suites from $210, children under 12 free.
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. Families (children must be 12 and older) book junior suites at the resort, which also has a tennis court and golf course. The hotel can arrange snorkeling trips, glass bottom boat and moped rentals. 600 Fleming St.; 800/869-4631 or 305/292-1919; www.marquesa.com; junior suites from $410.
Artist House This fabulous purple Victorian mansion has seven rooms and adornment to spare. Traditional Southern elements predominate: wingback chairs, four-poster beds, acres of swag-enough to make you want to put on a hoopskirt and a bustle. Although it's primarily a romantic getaway, this hotel suggests its two-bedroom villas for families with kids ages 13 and older. 534 Eaton St.; 800/582-7882 or 305/296-3977; www.artisthousekeywest.com; doubles from $139, teens $20.
Gardens Hotel Peggy Mills bought this 1870's house in 1930 and set about creating a showpiece botanical garden. She brought in 87,000 paving bricks, a Moorish fountain, and four tinajones, huge earthenware jars from Cuba that each weigh a ton. After her death, the place became a hotel with 17 rooms spread among five buildings. Breakfast—croissants, Key lime beignets—is served in the solarium. But you'll spend more time lolling in the pool, smelling the jasmine, and drinking a toast to Miss Peggy. Kids 10 and older welcomed. 526 Angela St.; 800/526-2664 or 305/294-2661; www.gardenshotel.com; doubles from $265, extra bed $20.
Heron House The three-building property is distinguished by artistic touches, such as stained-glass transom windows, intricately patterned brick patios, and a collection of rare orchids. The 23 rooms are large, with private decks and high ceilings; walls of teak or cedar marquetry add warmth. Kids must be 16 or older. 512 Simonton St.; 800/294-1644 or 305/294-9227; www.heronhouse.com; doubles from $189, teens $25.
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. Kids 12 and older allowed. 907 Truman Ave.; 800/352-6011 or 305/296-5152; www.lightbourn.com; doubles from $178, children $25.
A Florida Keys diet is bound to be plentiful in omega-3 and other fishy nutrients, but you'll get points off for breaded and fried. Thankfully, restaurants are warming to the healthful New World cuisine—tropical fruits and tubers, Latin-Caribbean flavors—that's ubiquitous in Miami and points north. In other words, the shrimp may be fried, but it will come with a mango-poppy seed dipping sauce. In the land of the laid-back, "formal" restaurants are happy to see kids, and the only dress code is a shirt and shoes. Seriously: A jacket is never required; ties are laughed at.
UPPER KEYS Fish House The line is long, the conch chowder peppery, and the catch of the day done eight ways (try Matecumbe-style: tomatoes, capers, shallots, basil, and lemon juice). And the nautical knickknacks lining the walls and strung on the ceiling are endlessly amusing. 102401 Overseas Hwy., Key Largo; 305/451-4665; dinner for four $100.
Snapper's Waterfront Seafood Restaurant On a mangrove-ringed inlet in Key Largo, Snapper's brings in the locals with killer rum drinks and good appetizers: cracked conch, blackened dolphin "fingers." All deep-fried items are hand-breaded, thank goodness. MM 94.5 Oceanside, Key Largo; 305/852-5956; dinner for four $140.