Book Luxury Villas in Grosseto

We selected the 1024 homes worth renting in this location

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Home spotlights in Grosseto

Green in Bloom

Green in Bloom

  • 10 guests

  • 5 bedrooms

Buonconvento, Siena

Boasting traditional Tuscan charm, this countryside villa welcomes up to ten guests, making it an excellent choice for a family or group of friends looking for a restful getaway. Inside, there’s plenty of space for the group to spread out, then come together for meals in the garden.

The Lucia

The Lucia

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

This quintessentially Italian home is nestled in the countryside just 5 kilometres from the beautiful town of Cortona. Days here can be spent hiking, cycling and exploring the historic hilltop towns of Tuscany.

Chianti Beauty

Chianti Beauty

  • 8 guests

  • 4 bedrooms

Vertine, Gaiole in Chianti

This Tuscan home is a bit special. It’s situated in the medieval hamlet of Vertine, close to the market towns of Gaiole in Chianti – just 2 kilometres away – and Radda, which is 7 kilometres away.

The Olive Stone

The Olive Stone

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shady stroll, and vineyards tumble down the hillside around you.


We selected the top 3% holiday homes in Grosseto Villas

Explore the 1024 most perfect homes in our collection

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Most popular homes in Grosseto

Sunny Shore

Sunny Shore

  • 10 guests

  • 4 bedrooms

Portoferraio, Livorno

Breathe The Green

Breathe The Green

  • 8 guests

  • 4 bedrooms

Sovicille, Tuscany

The Vine Song

The Vine Song

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Rustic Honey

Rustic Honey

  • 4 guests

  • 2 bedrooms

Casciana Terme Lari, Tuscany

Tuscan Hills

Tuscan Hills

  • 4 guests

  • 2 bedrooms

Monte Sante Marie, Asciano

Tuscan Twilight

Tuscan Twilight

  • 2 guests

  • 1 bedrooms

Arcidosso, Grosseto

The Lavender Harvest

The Lavender Harvest

  • 11 guests

  • 5 bedrooms

Manciano, Grosseto

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our Grosseto, Tuscany, Italy collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of Grosseto.

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