Editors' Note: Due to damage from Hurricane Omar, the Four Seasons is closed; it is due to reopen in February 2010.

Since opening in 1991, this property has become synonymous with the island, partly because of its size: 196 rooms on 350 acres. It's the only place here where service includes raked sand, a roped-off beach, and attendants who'll spritz you with Evian and roll up towels to support your back (lest the lounging cause too much stress). Even the simplest rooms have enormous marble bathrooms and mahogany furniture, while villas, scattered along Pinney's Beach and in the hills, have plunge pools and golf carts for zipping around. Dining options range from stuffy (the formal Dining Room) to scruffy (pick up buttery muffins and smoothies at the Sports Pavilion after your workout). Feeling antsy? Activities include golf at the Robert Trent Jones II–designed course, whacking a ball on one of ten tennis courts, and dodging the many kids swarming about. And at the 12,000-square-foot spa, rum isn't just a drink, it's a skincare tonic—just one of dozens of island-inspired treatments.

No lemons here: Each of the 26 individually decorated rooms in this oceanside 1610 French manor house has mahogany armoires and chests, fresh flowers, and enough tropical colors to outfit Jimmy Buffett's boudoir, thanks to Arthur Leaman, the former House & Garden editor who took over the property in 1963. It's romantic without being cheesy, refined without being snooty, and because of its location in a small fishing village, a refreshing escape from the heavily trafficked areas of St. Kitts. Just off the beach, the restaurant exudes old-money Antilles, with a cheery decor, signature breakfast porridge, and a new menu each night. Chilling out among the coconut trees is the main activity du jour, though there's good snorkeling and diving just offshore, nearby nature trails, a tennis court, and a large swimming pool. If you need AC, make sure you request it when booking; not every room has it.

Open October through July.

British naval hero Horatio Nelson and local girl Fanny Nisbet were married at this former sugar plantation in 1787—and it retains a sense of both romance and historic charm (note the two cannons, cast in 1696, guarding the entrance). The inn fell into disuse during the 20th century and was bought in 2002 by the Hoffman family, who improved it to the point that it's now a Relais & Châteaux property, one of a handful in the Caribbean. The building has a commanding view over the ocean from its position on a 750-foot-high hill, but the trade-off is that swimmers are relegated to using the hotel pool or taking a shuttle to a private beach six miles away. Montpelier's 17 rooms are furnished with island-made four-poster and canopy beds; atmospheric touches include orchids and monkey grass that dangle from bud vases on the walls. The staff is particularly attentive to service: They'll unpack your luggage if you ship it in advance, and won't bother you with paperwork when you arrive. There's also an extensive wine cellar and an intimate 18-seat dining room housed in an old sugar mill.

Open September through August.

This family-owned boutique property is on the site of a former lime plantation, and because of its location on the flanks of Mount Nevis, it just might have the best view on the island. The hotel is welcoming and homey—a feeling that emanates from the owners, Adly and Sally Meguid, who are Fantasy Island–friendly. The 30 rooms are spread among four peaked-roof pavilions; some have Jacuzzis or hot tubs and tasteful wicker furniture. Though it's a bit of a drive to get elsewhere on the island, the hotel's restaurant—offering dishes such as Cajun-grilled sea scallops, lobster ravioli, and mushroom risotto—and the charming staff will make you loath to leave. Plan a hike to the ruins of the plantation's 1822 chapel.

This onetime livestock plantation is "a very romantic British beachfront property" comprising a restored eighteenth-century great house and cottages sprinkled amid the foliage. Tropical-hued cottages with water-view terraces offer lots of "romance and privacy." Staff host weekly barbecues under the gingerbread trim and bamboo chimes at Coconuts. Explore the sea with complimentary snorkeling equipment.

(36 rooms)

Staying here is a lesson in privileged privacy. The idea is to offer the feeling of a house, but with no need to sweep up or do the dishes. Each of the three four-bedroom villas has its own houseman who will fetch drinks and hand you a towel as you hop out of the private waterfall pool. The villas themselves have hand-woven palm-frond roofs, hand-hewn doors, and Balinese furnishings chosen by designer Adam Tihany. A private chef whips up meals in the open-plan kitchen, and the 675-foot stretch of beach is an extension of the posh life. Just north of the Four Seasons, the hotel has thatched shelters and tall, swaying palm trees to shade guests from the sun—and prying eyes.