Enjoy the breeze from the rooftop lounge at Olive Boutique Hotel (from $179), an elegant, Mediterranean-inspired 15-room property in the centrally located Condado district. Ask for one of the more spacious O:Lifestyle suites, which have open-plan bathrooms, reclaimed-wood desks, and all-glass spa showers stocked with L’Occitane toiletries, not to mention Nespresso machines. The Old World-meets-modernity theme spills into the cozy restaurant, where Argentinean chef Nicolás Gomez serves updated classics like foie gras with organic pumpkin marmalade ($21) and gnocchi with pistachio pesto ($22).
Mingle with health-conscious travelers at Dreamcatcher (from $65), an intimate two-year-old guest house with a vegetarian kitchen doling out communal dinners. Everything about this inn promotes relaxation, from its location in a quiet, residential seaside neighborhood to the hammocks hanging in unexpected corners, and the flower-filled garden dotted with buddha statuettes. All ten rooms are furnished with handpicked vintage, themed pieces: pendant lanterns and kilim rugs in the Moroccan suite; built-in bookshelves painted bright green in the library. Sign up for a yoga class, held at sundown around a fragrant lemon tree, or for a paddleboard lesson taught in a nearby pond.
Take in the scenery at La Concha (from $219), a gorgeously renovated Modernist hotel originally built in the 1950s. Eye-catching period features include a seashell-shaped restaurant that appears to be floating on water and an ample brise-soleil (a sun-shading structure popularized by Le Corbusier) at the entrance, but everything else has been reinvented, starting with the expanded lobby, clad entirely in white Calacatta marble and strewn with leather wingback chairs orbiting a busy central bar. Scope out the scene while sipping a mango caipirinha ($11), then claim a chair by the two-tiered pool right outside. Request a room in the all-suite tower for perks like sun-drenched balconies, Saarinen furnishings, and direct access to another adults-only pool.