Villa Talamo Grosseto villa with tower and palm trees

Grosseto Vacation Rentals

Tucked away on the shores of the Tyrrhenian Sea on the coast of Tuscany, Grosseto is an enigmatic and historic city in Italy’s most famous province. The city center of Grosseto is encircled by intact stone walls, preserving the ancient feel of the place, and with countless historical buildings and attractions, a vacation in Grosseto is like taking a trip back through time itself.

Our Grosseto vacation rentals also have a touch of something historic about them. From authentic stone farmhouse-style homes to palatial villas, these incredible rentals look right at home in the rolling hills of the Tuscan countryside. Sleeping as many as 26 guests in complete luxury, and with fantastic facilities including private pools, housekeeping and chef services, and pet-friendly features, our Grosseto vacation rentals are the perfect choice for unforgettable adventures in Italy.

Grosseto central plaza with old European buildings around the square

Distances from Grosseto

DestinationDrive time (mins)Distance (miles)
Rome2 hours 30125
Pisa1 hour 35100
Florence1 hour 5595
Siena6046
Isle of Elba (by sea)2 hours 2077
Pisa Airport1 hour 35100

Things to do

  • An historical piazza in Grosseto, Tuscany
    Explore Grosseto's Historic Center
    Immerse yourself in the charming medieval streets of Grosseto's historic center. Explore the Piazza Dante Alighieri, admire the Cathedral of San Lorenzo, and explore alleys lined with shops, cafes, and ancient buildings.

  • Flamingo rest in the Diaccia Botrona nature reserve
    Visit the Diaccia Botrona Nature Reserve
    Nature enthusiasts will love the Diaccia Botrona, a unique wetland reserve teeming with diverse bird species and lush flora. Take a leisurely stroll along the well-marked trails or enjoy a guided boat tour!

  • Discover ancient wonders in the Grosseto Archaeological Museum
    Visit the Grosseto Archaeological Museum
    Delve into the rich history of the region at the Archaeological Museum. Discover ancient artifacts, Etruscan and Roman relics, and well-preserved archaeological treasures that provide insight into the area's fascinating past.

  • A group of female friends enjoy wine tasting in a Tuscan vineyard
    Go Wine Tasting in the Tuscan Countryside
    Indulge in a wine-tasting journey through the enchanting Tuscan countryside surrounding Grosseto. Visit local wineries, sample renowned wines like Morellino di Scansano, and savor the exquisite flavors that this region is celebrated for.

  • A horse and foal enjoy the sunshine in the Maremma Regional Park
    Go to the Maremma Regional Park
    Embark on a nature-filled adventure in the Maremma Regional Park. Hike through the unspoiled landscapes, relax on pristine beaches, and witness the picturesque harmony of lush countryside and azure waters.

  • The peaceful beach of Punta Ala in Grosseto
    Soak up the Punta Ala Beach
    Bask in the sun and unwind on the idyllic Punta Ala Beach. With its golden sands and clear waters, it's a perfect spot for swimming, sunbathing, and engaging in various water sports, making it a haven for beach lovers.

  • A view of the hilltop Rocca di Montemassi castle in Grosseto
    Visit Rocca di Montemassi
    Experience medieval allure at the Rocca di Montemassi, a historic castle that offers panoramic views of the surrounding countryside. Explore the castle's interiors, walk the battlements, and immerse yourself in the ambiance of centuries past.

  • Fool's gold in a Tuscan mine
    Explore the Gavorrano Mines
    Uncover the industrial heritage of Grosseto by visiting the Gavorrano Mines. Take a guided tour through the abandoned mine complex, learning about the mining history that once played a significant role in the area's economy.

Luxury Vacation Rentals

Award winning portfolio of the best vacation homes and villas in the world’s top destinations

Travel Planners

Experienced vacation rental and villa experts to help you find the perfect home

Concierge & Support

Enjoy 5-star hotel concierge services and dedicated local support with every stay

Sunset over a Tuscan dinner party

Luxury Travel Extras for Grosseto villa stays

With luxury optional Travel Extras including car hire, villa staff, private chef, wine tasting, pasta making experiences, tailor-made itineraries and more, Top Villas make it easy to live out "La Dolce Vita" in your Grosseto villa.

We also offer a host of family-friendly concierge services to take the hassle away from your family vacation in Tuscany - enabling you to fully kick back and relax!

Dream up your best vacation yet, with our optional luxury concierge services. Designed to bring effortless experiences to your villa front door, we are here to make your Tuscany vacation as memorable and enjoyable as it can be.

Villas in Grosseto, Italy, with private pools Casale Montegiovi villa with large private pool and sun loungers

Grosseto vacation rentals with private pools

Tucked away on the shores of the Tyrrhenian Sea on the coast of Tuscany, Grosseto is an enigmatic and historic city in Italy’s most famous province. The city center of Grosseto is encircled by intact stone walls, preserving the ancient feel of the place, and with countless historical buildings and attractions, a vacation in Grosseto is like taking a trip back through time itself.

Our Grosseto vacation rentals also have a touch of something historic about them. From authentic stone farmhouse-style homes to palatial villas, these incredible rentals look right at home in the rolling hills of the Tuscan countryside. Sleeping as many as 26 guests in complete luxury, and with fantastic facilities including private pools, housekeeping and chef services, and pet-friendly features, our Grosseto vacation rentals are the perfect choice for unforgettable adventures in Italy.

Book with Confidence

With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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A terrier dog explores a Tuscan vineyard in the September light

Pet friendly Grosseto villas

Guests looking to bring the whole family will relish our super collection of pet-friendly Grosseto villas. Featuring Grosseto villas with pools, expansive shady terraces and sprawling private gardens, our finest Grosseto homes provide an idyllic oasis in which you and your pet can unwind, as well as a convenient base from which to explore the delights (and walks) of Tuscany.

Inside, enjoy the cosy Tuscan warmth of inviting living areas and airy rooms, with the cooling respite of air-conditioning, which features to many of our pet-friendly Grosseto villas.