8. Round Hill Hotel & Villas 78.95
Montego Bay, Jamaica

Direct Flights Per Week From North America: 220
Number of Rooms/Units with Kitchens: 110/0
Kids’ Club Rate: Free
Number of Pools: 2

A former sugar plantation west of Montego Bay, Round Hill has exuded Grace Kelly chic since 1953 (daily afternoon tea, no TV’s, oodles of service), yet its 25 villas, each with a private pool, make it perfect for families. The Pineapple Club is base camp for T-shirt tie-dying and jungle explorations, and the shallow end of the dazzling new pool was designed with minnows in mind. Key Fact In addition to the villas, consider Pineapple House—it has connecting rooms. Doubles from $590.

9. Beaches Negril Resort & Spa 78.37
Negril, Jamaica

Direct Flights Per Week From North America: 220
Number of Rooms/Units with Kitchens: 210/0
Kids’ Club Rate: Free
Number of Pools: 3

An all-inclusive on Jamaica’s famed Seven Mile Beach, Beaches Negril has the well-honed distractions for which the chain is famous: accredited nannies, walk-around Sesame Street characters, and a water park with self-serve ice cream, not to mention snorkeling jaunts, Xbox challenges, and G-rated reggae parties. Key Fact The Savannah block is closest to the action. 800/232-2437; www.beaches.com; adults from $370, kids 2-15 from $95, all-inclusive.

10. Westin St. John Resort & Villas 78.27
St. John, USVI

Direct Flights Per Week From North America: 100
Number of Rooms/Units with Kitchens: 174/92
Kids’ Club Rate: $30/Half-Day
Number of Pools: 1

The Westin’s palmy property slopes gently down to tranquil Great Cruz Bay, where kids bounce on giant water trampolines, splash in the pool’s waterfall, and go on iguana safaris. Try the on-site family activities (bingo, potato-sack races) or day-trip to the island’s spectacular snorkeling beaches. Key Facts First-floor Pool View doubles have their own patios. Secluded villas offer even more privacy—exactly what the Caribbean was made for. Doubles from $759.