Grosseto Luxury Houses

Award-winning homes from £98

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Home spotlights in Grosseto

Valley of Heaven

Valley of Heaven

  • 8 guests

  • 4 bedrooms

Castiglione d'Orcia, Siena

Fall in love with the timeless charm of Tuscany from this home perched on the hills of Val D’Orcia. Outside, days can be spent by the saltwater pool and lounging under ancient oak trees.

Verbena & Rosemary

Verbena & Rosemary

  • 17 guests

  • 8 bedrooms

Pomarance, Pisa

This Tuscan home is something special. It’s in the Val di Cecina, close to the medieval town of Pomarance, with its historic castle and walls.

Olive Delight

Olive Delight

  • 9 guests

  • 5 bedrooms

Castiglione della Pescaia, Grosseto

Nestled in the Maremma countryside and surrounded by olive groves, a mere four kilometres from the beach of Castiglione della Pescaia, this charming villa waits to welcome you home. It’s worth noting that the keeper lives on-site in a separate home near the entrance gate, and there’s an annexe on-site for the exclusive use of the owner, but don’t let that detract from everything this home offers.

The Tuscan Star

The Tuscan Star

  • 8 guests

  • 4 bedrooms

Grosseto, Tuscany

Tucked away in the sleepy hills of the Tuscan Maremma, this rustic home offer tradition and comfort along with incredible views. From here, leisurely days can be spent by the pool or relaxing on the veranda.


We selected the top 3% holiday homes in Grosseto Houses

Explore the 1028 most perfect homes in our collection

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Most popular homes in Grosseto

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

Pines & Vines

Pines & Vines

  • 10 guests

  • 5 bedrooms

Rosignano Marittimo, Livorno

Tranquil Tuscan Retreat

Tranquil Tuscan Retreat

  • 12 guests

  • 6 bedrooms

Buonconvento, Siena

Tuscan Valleys

Tuscan Valleys

  • 8 guests

  • 4 bedrooms

Manciano, Grosseto

Lavender & Wine

Lavender & Wine

  • 6 guests

  • 4 bedrooms

Gavorrano, Grosseto

Rolling Hills of Tuscany

Rolling Hills of Tuscany

  • 6 guests

  • 3 bedrooms

Campagnatico, Grosseto

The Vine Song

The Vine Song

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

La Casa di Pietra

La Casa di Pietra

  • 8 guests

  • 4 bedrooms

San Casciano dei Bagni, Tuscany

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Frequently asked questions

All Plum Guide houses in Grosseto, Tuscany, Italy have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each house in Grosseto, Tuscany, Italy before approving it, so you can book with peace of mind.

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