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We selected the 1026 homes worth renting in this location

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Home spotlights in Grosseto

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.

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.

Citrus Pavillion

Citrus Pavillion

  • 20 guests

  • 9 bedrooms

Gaiole in Chianti, Siena

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest.

Cypresses & Herbs

Cypresses & Herbs

  • 11 guests

  • 6 bedrooms

Campagnatico, Grosseto

This restored stone farmhouse, in the rolling hills of the Tuscan Maremma, is surrounded by olive groves and vineyards. The fenced garden is dotted with cypresses and aromatic herbs and the sun terrace near the private saltwater pool has stunning views of the surrounding countryside.


We selected the top 3% holiday homes in Grosseto Villas

Explore the 1026 most perfect homes in our collection

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Most popular homes in Grosseto

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

Rustic Honey

Rustic Honey

  • 4 guests

  • 2 bedrooms

Casciana Terme Lari, Tuscany

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Vines & Vistas

Vines & Vistas

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Pink Terracotta

Pink Terracotta

  • 6 guests

  • 3 bedrooms

Ansedonia, Orbetello

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Aqua Olive

Aqua Olive

  • 8 guests

  • 4 bedrooms

Manciano, Grosseto

The Vine Song

The Vine Song

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

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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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