Book Luxury Holiday Rentals in Grosseto

Award-winning homes from £98

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Home spotlights in Grosseto

Escaping Time

Escaping Time

  • 7 guests

  • 3 bedrooms

Sovicille, Tuscany

Nestled in a sea of pea-green pastures, historic olive groves, and undulating hills, this home exudes Tuscan tranquillity. You'll find it in the little village of Brenna, just a forty-minute drive from Siena.

Pistachio Pesto

Pistachio Pesto

  • 8 guests

  • 2 bedrooms

Arezzo, Tuscany

This home is a true haven nestled right in the heart of Arezzo. With its luscious garden and rustic interior, it's the perfect place to kick back and relax away from the hustle and bustle.

Rusticana Retreat

Rusticana Retreat

  • 14 guests

  • 7 bedrooms

Castiglione d'Orcia, Siena

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside.

Tuscany Elegance

Tuscany Elegance

  • 4 guests

  • 2 bedrooms

Roccastrada, Grosseto

This Tuscan home is in a peaceful spot, surrounded by trees and meadows. We love the dining room here, which opens out onto the private garden and boasts countryside views.


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

Explore the 1422 most perfect homes in our collection

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Most popular homes in Grosseto

Love & Serenity

Love & Serenity

  • 10 guests

  • 4 bedrooms

Grosseto, Tuscany

Forever Views

Forever Views

  • 10 guests

  • 5 bedrooms

Civitella in Val di Chiana, Tuscany

The Vine Song

The Vine Song

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

Honey & Lavender

Honey & Lavender

  • 10 guests

  • 5 bedrooms

San Casciano dei Bagni, Tuscany

Asian Fusion

Asian Fusion

  • 8 guests

  • 4 bedrooms

Montecatini Val di Cecina, Pisa

Rustic Honey

Rustic Honey

  • 4 guests

  • 2 bedrooms

Casciana Terme Lari, Tuscany

Wild Branch

Wild Branch

  • 6 guests

  • 3 bedrooms

Campagnatico, Grosseto

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Grosseto, Tuscany, Italy. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Grosseto, Tuscany, Italy has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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