St. Kitts: Rawlins Plantation Inn
St. Kitts' Rawlins Plantation Inn, sprung from the remnants of a 17th-century sugar plantation, is intimate -- only 10 rooms -- with a spring-fed pool and the best chicken curry at its lunch buffet. Book the suite in a restored sugar mill; rates from $341, including breakfast and dinner. rawlinsplantation.com

Anguilla: Cap Juluca
Moorish in design -- think domed villas, dramatic archways and elaborate tiling -- Anguilla's Cap Juluca is privy to 2.5 miles of snow-white beach on which pear, mango and passion-fruit sorbets are served each afternoon. Some luxury rooms have winding staircases that lead to private sun terraces. Luxury room rates from $485, including breakfast. capjuluca.com

Grenada: Laluna
Laluna's minimalist thatched-roof cottages traipse down the hillside of southwestern Grenada. Within you'll find carved Balinese four-posters decked with gauzy linens, day beds on the lanai and open-air (though private) bathrooms from which you can watch the tides as you shower. Beachfront cottage rates from $570. laluna.com

Puerto Rico: The Horned Dorset Primavera
The Horned Dorset Primavera lounges along Puerto Rico's western seaside, a few minutes' drive from Rincón. Tuck into a Primavera Suite: a two-storied villa embellished with grand furnishings and private balconies containing sheltered plunge pools. Primavera rates from $590, including breakfast and dinner. horneddorset.com

Grenadines: Firefly Mustique
From its high perch, über-cool Firefly reigns over Mustique's Britannia Bay. Of its five rooms, we love the Tree House where the best ocean views are from your bed. Pick your poison: Will you join the champagne or martini club? Tree House rates from $750, including all meals. fireflymustique.com