Grosseto Luxury Rentals

We selected the 264 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.

Love & Serenity

Love & Serenity

  • 10 guests

  • 4 bedrooms

Grosseto, Tuscany

With stunning views across the Tuscan Maremma, this home will captivate you from the moment of arrival. There’s a peaceful garden, a private pool and a terrace for magical evening meals.

Peace in Tuscany

Peace in Tuscany

  • 12 guests

  • 6 bedrooms

Montepulciano, Siena

With idyllic views stretching across vineyards, olive groves and rows of cypresses, it’s not hard to see why this home caught our eye. Dating back to the 18th-century, the house has since been restored into a restorative retreat – one that will leave you feeling refreshed from the moment of arrival.

The Hilltop Dream

The Hilltop Dream

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining.


We selected the top 3% holiday homes in Grosseto Luxury Rentals

Explore the 264 most perfect homes in our collection

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Most popular homes in Grosseto

The Old Watermill

The Old Watermill

  • 14 guests

  • 7 bedrooms

Montepulciano, Siena

Texture Like Sun

Texture Like Sun

  • 16 guests

  • 10 bedrooms

Cetona, Siena

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

A Sweet Symphony

A Sweet Symphony

  • 4 guests

  • 2 bedrooms

La Dogana, Cortona

Sixteenth Century

Sixteenth Century

  • 24 guests

  • 12 bedrooms

Campiglia Marittima, Livorno

The Tuscan Moon

The Tuscan Moon

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

The Vines of Tuscany

The Vines of Tuscany

  • 18 guests

  • 9 bedrooms

Gavorrano, Grosseto

The Sunlight Hideaway

The Sunlight Hideaway

  • 12 guests

  • 6 bedrooms

San Vincenti, Tuscany

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Frequently asked questions

A handpicked selection of the best luxury homes in Grosseto, Tuscany, Italy, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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