Book Luxury Monthly Rentals in Grosseto

We selected the 1296 homes worth renting in this location

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Home spotlights in Grosseto

Cypress Hill

Cypress Hill

  • 12 guests

  • 6 bedrooms

Città della Pieve, Perugia

The Italian countryside has a magnetic charm. Could it be the holy trinity of wine, food and verdant views?

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.

Tuscan Medley

Tuscan Medley

  • 10 guests

  • 5 bedrooms

San Casciano dei Bagni, Tuscany

Nestled high on a hill in the Sienese countryside, this enchanting villa offers the perfect escape from your everyday. Ideal for large groups or families, there's ample room to make memories and enjoy some downtime on your own.

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens.


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

Explore the 1296 most perfect homes in our collection

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Most popular homes in Grosseto

Rolling Hills of Tuscany

Rolling Hills of Tuscany

  • 6 guests

  • 3 bedrooms

Campagnatico, Grosseto

The Main Event

The Main Event

  • 10 guests

  • 5 bedrooms

Metelliano, Cortona

Tuscan Trees

Tuscan Trees

  • 6 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

Lavender & Wine

Lavender & Wine

  • 6 guests

  • 4 bedrooms

Gavorrano, Grosseto

Flora Fortress

Flora Fortress

  • 12 guests

  • 9 bedrooms

Paciano, Perugia

The Lucia

The Lucia

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

Cypresses & Herbs

Cypresses & Herbs

  • 11 guests

  • 6 bedrooms

Campagnatico, Grosseto

Love & Serenity

Love & Serenity

  • 10 guests

  • 4 bedrooms

Grosseto, Tuscany

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Grosseto, Tuscany, Italy, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Grosseto Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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