Set around two large courtyards filled with lush greenery and leafy palm trees, this hotel is where heiress Marjorie Merriweather Post crashed while prepping her manse Mar-a-Lago for the season. The hotel was designed in 1926 by Rosario Candela (the architect behind some of Manhattan's swankest Fifth Avenue apartment buildings) and got a face-lift in late 2007 that redesigned the still very British-colonial rooms with mahogany and Hauteville Doré limestone. The Brazilian Court continues to attract society types who prefer the privacy of the 80-room inn versus the Breakers, which is almost seven times the size. (The Brazilian Court also skips the Breakers's beachfront location, family-friendly fun, tennis courts, and golf course.) What the hotel lacks in activities it makes up for in big-name amenities: The salon is Frédéric Fekkai and the restaurant is Café Boulud, which provides room service until 11 pm.

Aah, the Breakers—one of the most famous, most exclusive, and yes, priciest places to stay in America (it's even snagged a spot on the National Register of Historic Places). Since its opening in 1896, the 550-room Breakers has played host to generations of great families—and those willing to pay big bucks to mix with the great families—during the social season. This 140-acre oceanfront Italian Renaissance–style property has extraordinary views, exceptional service, and amenities galore: Book in here for two 18-hole championship golf courses, three fitness centers, a beach club with fancy cabanas and water sports, five swimming pools, ten tennis courts, a 20,000-square-foot spa, and eight restaurants, most notably gourmet French spot L'Escalier. Lifelong visitors might remember the Breakers' rooms during the less-than-glorious 1990s, when they were, frankly, a little dingy and careworn. The owners have spent $250 million since then, updating the rooms and ensuring guests have access to high-speed Internet while they lounge on the gilt-and-floral furniture.

This is a British expat favorite—note the Union Jack fluttering above the entrance—with 52 rooms decorated to make these guests feel right at home. Flouncy bedspreads, heavy drapes, and antique-style desks seem borrowed directly from a chintzy English country house, though the huge TVs are flat-screens. There's a smallish pool with striped awnings and metal furniture that give a whiff of vintage Agatha Christie (the beach is three blocks away). The after-hours spots are worth stopping in even if you aren't staying at the hotel: The cigar menu at the Churchill Room is intense (pair a $25 Savinelli with a $175 shot of Louis XIII Remy Martin) and the Leopard Lounge is one of the few buzzy spots for an evening drink on the Island. That, and the hotel's quirky/quaint details—dishes of jelly beans everywhere, satisfyingly hefty old-fashioned room keys instead of electronic cards—lend the Chesterfield a sense of whimsy sorely missing from other Palm Beach hotels.

This 90-room hotel is a youngster by Palm Beach terms—it was only built in 1947—but it echoes its neighbors' hushed, moneyed elegance (the Florida-shaped swimming pool's a waggish touch). Like most of the hotels on the Island, the Colony is only a couple blocks from the beach and just a block from Worth Avenue. A five-year, $13 million makeover upgraded the admittedly still pocket-size rooms with breezy yellow decor inspired by the British West Indies. But if you are staying at the Colony, you are here for the legendary suites. The Duke and Duchess of Windsor crashed in the penthouse during their itinerant post-abdication exile, and last year the hotel finally honored the renegade royals by renaming the 1,900-square-foot, two-bedroom penthouse in their honor. (Look for the framed check His Royal Highness used to pay the $1,000 bill back in 1961—now, rates start at $2,000 a night.) Across the road from the main building is the Colony's most exclusive enclave. The circa-1928 Casa Manana has been turned into seven stand-alone villas, available in season for monthly rentals from $20,000 to $30,000. That monthly charge is a hint at the clientele here: largely longtime regulars who hole up in Palm Beach for a chunk of the chilly northern winter. Their dominance helps give the hotel a pleasant, homey vibe. Nightlife here also fits with the laid-back atmosphere, with a steak house that doubles as a piano bar and the Royal Room Cabaret.

Tucked away amid the hedgerow-hidden mansions a little ways out of town, this 210-room property provides all the pampering you'd expect from a luxury resort, from the warm smile of the valet to the ever-present pool attendants who bring chilled facecloths to your side while you sunbathe. Nearly every room has a generous ocean view, and there are lush gardens and AAA Five Diamond dining. The Spa offers extensive traditional and contemporary services, either in-room or on-site. Championship golf at nearby courses, three tennis courts, fishing and water sports, and a heated freshwater pool with cabanas are among the activities at your beck and call. Good news for families: Children under 18 can share the room for no extra charge. The supervised Kids for All Seasons activity program is available for children under 13, and teens have their own game room. Not as old-school grand or as conveniently located as the Breakers, but a good choice for the chintz-phobic, and the concierge service is exceptional.

Those looking for a hip, modern alternative to British colonial and Italian Renaissance will feel more at home at this former motor lodge in West Palm Beach, just over the bridge from the Island. British designer Barbara Hulanicki breathed new life into it when she took it over in 2001. The Swinging Sixties London icon, famed for her Biba label, filled the 46 rooms with mod furniture and her trademark citrus colors: orange walls, lots of plexiglass, and crisp white sheets. All of the usual hotel amenities are there as well. Bathrooms are stocked with Aveda products and the tech is up to date (flat-screen TVs, high-speed Wi-Fi). A breakfast of sticky Cuban pastries is served in the Biba Bar every morning and the bar's Asian-style garden is the perfect place for a nightcap. The location in the El Cid district also puts it right near the shops, restaurants, and bars on Clematis Street.

It's a stretch to put "Palm Beach" in the name of this Ritz-Carlton, since the beachfront resort sits a ten-mile drive down the coast from Worth Avenue. But it's designed to be a destination in itself. The beach is the main attraction: Though the seven-acre strand is not private like the one at the Breakers, the out-of-the way location keeps it from getting as crowded as the public beaches in Palm Beach proper. The Ritz reopened in March 2007 after an eight-month shutdown for renovation of the 310 rooms, to which were added now-expected details like Wi-Fi and flat-screen TVs. A lot of work went into the suites' bathrooms, which now have huge tubs carved from single slabs of stone and angled to have ocean views. The three restaurants were also updated: Breeze Beach Bar; the casual Temple Orange (modern Italian); and Angle, a dark, candlelit spot with an extensive seafood menu. The hotel also added oceanfront cabanas that have stocked fridges, flat-screen TVs, and iPod docking stations for a sybaritic day on the beach. An extensive kids' program takes advantage of the ocean and nature sites around the hotel. One caveat: Construction at the new Eau Spa (due to open winter 2008–09 with a 42,000-square-foot spa) can make it noisy on weekdays.