A circular pool tilts toward the sky like an art installation at this gallery-like retreat near Estremoz. Set amid nearly 300 acres of olive groves on the rolling hills of Portugal’s Alentejo region, the villa offers a glimpse into the area’s olive-oil-producing past even as it looks to the future in an avant-garde art collection. It’s a short drive to beaches and marble castles.

Tip your face to the expanse of sky from one of the 2 pools, a lounger on the terrace, or the rooftop terrace. Find sculptures tucked into garden nooks on a stroll beneath the olive trees, a barbecue waiting for fresh seafood, and a covered alfresco dining area for 10. The highlight might be the property’s art gallery, though, which is set in a circa-1904 olive oil press and filled with furniture and sculpture—art you can walk amongst.

Like the white cobblestones fanning out in the courtyard, marble splashes on the surfaces inside the villa for an understated-luxe vibe. The open-plan living and dining room is spare but stunning, with wood furnishings and large-scale paintings that could be in the art gallery. A fully equipped kitchen shows a practical side to match the artistic one.

Spot the castle of Estremoz from the terrace, then take a morning or afternoon to visit this hilltop city, whose marble-clad architecture spans centuries. It’s also an easy drive from the villa to the chic eateries of the Comporta area.

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