Tres Sirenas Inn, Rincón
Price: Doubles, $175
Facing a placid swimming beach, this elegant B&B has only four units—two rooms, a studio, and an apartment. All of them are spotless and tastefully appointed with plush white upholstery and terra-cotta tiles, and each room has lots of big windows to frame an ocean view. Gourmet breakfasts are served on a waterfront terrace, and kayaks, snorkeling gear, and surfboards are available for use on the beach. Rooms are outfitted with TVs, ceiling fans, and air-conditioning.
Book: The airy and spacious Sea View Apartment, for $270 (787-823-0558; tressirenas.com).
Best for: Beach bums who require creature comforts.
Rental car: Not required—you can take a bus here from San Juan, and the beachfront has lots of dining and nightlife options.

Bravo Beach Hotel, Vieques Island
Price: Doubles, $210–$295
At this chic and cheerful updated version of a seaside motel, each of the nine rooms features fine linens, modern furnishings, and amenities that include iPod docking stations and yoga mats. Numbers 3 through 9, as well as the adjacent two-bedroom villa, overlook the sea, but the prime swimming spots are a 10- to 15-minute drive away. Too lazy to make the trip? Content yourself with a dip in one of the two small swimming pools, and then chill out on the shady patio with a grilled pizza and a bottle of pinot grigio from the hotel's fine restaurant.
Book: Any oceanfront room (787-741-1128; bravobeachhotel.com).
Best for: Urban hipsters who crave good wine with their sea views.
Rental car: Required for accessing the best beaches; a handful of good restaurants are within walking distance.

MEXICO

Amansala, Tulum
Price: Doubles, $175–$225
A collection of thatched huts and stone villas near the "it" town of Tulum, Amansala is boho-chic at its finest. Rooms come with plush beds draped in gauze, but it's the weeklong bikini boot camps filled with hikes, bike rides, massages, tasty low-cal fare, and classes in everything from belly-dancing to creative writing that Amansala is famous for. Not up for training? Laze on the white sand beach, take a dip in the sea, or explore nearby ruins.
Book: Room 11 is big and beachfront with a private terrace (amansala.com).
Best for: An active adventuress looking for total detox.
Rental car: Not required. Tulum is two hours south of Cancún; opt for an airport shuttle instead of the Amansala van, which charges up to $130 per person.

ST. LUCIA

Ti Kaye Village Resort, Anse Cochon
Price: Doubles, $280–$355
Ti Kaye Village, on St. Lucia's west coast, is arrayed on a jungly hillside that tumbles into the Caribbean. All 33 gingerbread cottages have ocean views, four-poster beds, patios, hammocks built for two, and outdoor showers. Past the pool, at the bottom of a 166-step staircase, is a narrow wedge of sugary sand­—the perfect launch site for snorkeling and diving in the adjacent bay.
Book: One of the higher rooms, to be near the restaurant (758-456-8101; tikayevillage.com).
Best for: Athletic couples.
Rental car: Not required, but the island is worth exploring, and rentals are cheaper than taxis.