Luxury Long Stay Rentals in Grosseto

We selected the 1070 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Grosseto

Sunny Shore

Sunny Shore

  • 10 guests

  • 4 bedrooms

Portoferraio, Livorno

With direct access to Padulella Beach, this villa guarantees a memorable stay on the island of Elba. Outdoor living is encouraged here, thanks to the summer kitchen complete with a wood oven, infinity pool and a covered terrace overlooking the Tyrrhenian Sea.

The Tuscan Muse

The Tuscan Muse

  • 14 guests

  • 7 bedrooms

Tregole, Tuscany

With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together.

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

Surrounded by olive groves and ancient woods, this traditional farmhouse welcomes you to an authentic stay in the heart of Tuscany. Located on Pomaio hill with sweeping views across the countryside, this is a wonderful setting to retreat into the heart of nature.

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena. Located in the historic town of Montalcino (renowned for its Brunello wine), this is the perfect setting to experience the warmth and depth of Italian living.


We selected the top 3% holiday homes in Grosseto Long Stay Rentals

Explore the 1070 most perfect homes in our collection

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Most popular homes in Grosseto

Two Seas

Two Seas

  • 12 guests

  • 6 bedrooms

Punta Ala, Castiglione della Pescaia

Tuscan Delight

Tuscan Delight

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Artistic Grapes

Artistic Grapes

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Wild Branch

Wild Branch

  • 6 guests

  • 3 bedrooms

Campagnatico, Grosseto

Sweet Tuscany

Sweet Tuscany

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Put Your Loving Arms Around Me

Put Your Loving Arms Around Me

  • 13 guests

  • 7 bedrooms

Sarteano, Siena

The Ancient Stone

The Ancient Stone

  • 11 guests

  • 5 bedrooms

Cortona, Arezzo

Wave & Pine

Wave & Pine

  • 8 guests

  • 4 bedrooms

Roccamare, Castiglione della Pescaia

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Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Grosseto, Tuscany, Italy. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Grosseto, Tuscany, Italy collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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