Book Luxury Vacation Rentals in Grosseto

Award-winning homes from £98

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Home spotlights in Grosseto

The Chianti Hills

The Chianti Hills

  • 8 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves.

Sunflower Sunset

Sunflower Sunset

  • 8 guests

  • 4 bedrooms

Pienza, Siena

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside.

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

Perched on the hills overlooking the Val di Chiana, this beautiful home seamlessly blends rustic charm with elegant Tuscan style to create a truly unforgettable stay. Less than a fifteen–minute walk from the centre of Cortona, the owners have thoughtfully restored this traditional farmhouse into a welcoming space that exudes charm.

The Tuscan Farm

The Tuscan Farm

  • 14 guests

  • 7 bedrooms

Sovicille, Tuscany

Whether you’re here for the famous landscapes, rich history, culture or cuisine, one thing’s for sure, if you want to experience Tuscany at its finest, this charming villa is the place to be. In an idyllic countryside location, this home is surrounded by luscious greenery, rolling hills and landscapes, making it the ideal spot for sunset views and stargazing.


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

Explore the 1550 most perfect homes in our collection

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Most popular homes in Grosseto

The Sweet Heart

The Sweet Heart

  • 2 guests

  • 1 bedrooms

Porto Santo Stefano, Tuscany

Lighthouse Island

Lighthouse Island

  • 4 guests

  • 2 bedrooms

Grosseto, Tuscany

The Olive House

The Olive House

  • 10 guests

  • 5 bedrooms

Murlo, Siena

Pistachio Pesto

Pistachio Pesto

  • 8 guests

  • 2 bedrooms

Arezzo, Tuscany

The Tuscan Moon

The Tuscan Moon

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

Bellissima Casa

Bellissima Casa

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Grosseto. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Grosseto Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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