A former sugar and pineapple plantation near Montego Bay, Jamaica's upscale Round Hill Resort and Villas opened in 1953 as a retreat for socialites and celebrities. Regulars included John and Jackie Kennedy, Cole Porter, and Clark Gable, and Rogers and Hammerstein wrote "The Sound of Music" in one of the villas. These days, the place still channels a retro vibe with its old-school service and afternoon tea, even as it introduces modern perks like resortwide Wi-Fi.

There are 36 designer-chic oceanfront rooms in the Pineapple House and 27 two- to five-bedroom villas, most with private pool. At the water's edge is a trio of pools (infinity, wading, and spa) and a private beach and watersports center offering PADI diving, deep-sea fishing, and yachts available for charter. Round Hill also boasts complimentary tennis, with five all-weather courts (two illuminated for evening play), a spa, fitness center, and complimentary kids' club for kids 3 to 12.

Call 800/972-2159 to book a three-night stay between now and December 14, and you'll get your fourth night free. Plus, if you book an oceanfront room in the Pineapple House (rates from $490 through December 14), you can take advantage of a family-friendly offer that includes an adjoining room at half price, plus five hours a day of free nanny service. Kids 12 and under get a 50% discount on the meal plan, and there's no charge to get a crib, cot, or fridge in your room.