Namesake umbrella pines and sheets of glass filter sunshine at this low-slung, boho-chic retreat near Carvalhal. Its pairing of contemporary architecture with a laid-back look—think woven accents and invitingly deep sofas—captures the casual vibe of Comporta, where A-listers come to cycle barefoot. It’s a 10-minute drive to 2 of the area’s sandy, restaurant-lined beaches.

Ease into mornings over a cup of coffee at the shaded outdoor sitting areas, then move to a lounger by the fenced-in pool or strike up a lawn game as the sun creeps across the grass. Work on your volley on the tennis court before heating up the charcoal barbecue for an alfresco dinner and unwinding in the media and games rooms for the evening.

Clean lines, glass walls, and blocky stone floors erase the boundaries between indoors and out. Sunlight streams across the 2 sitting areas in the living room and the dining room next door. A waterfall-counter-topped island brings stone texture (and a practical work surface) into the fully equipped kitchen.

From the villa’s private setting atop a private lawn, it’s a 10-minute drive to the Carvalhal and Comporta beaches, stretches of sand that are backed by dunes and fronted by restaurants serving up fresh seafood. Brave the Atlantic waters during a surfing lesson or see the landscape from higher up on a horseback ride, then head into town for one-of-a-kind shopping and avant-garde cuisine.

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