Vacation rentals in Cerchiaia

The little house

We open the doors of our house in the countryside of Siena, 7 minutes by bus from the center (bus stop 2 minutes away). A small, functional nest, designed to make you feel at home, ideal for couples or singles. It offers a double bedroom and a small bedroom with a sofa bed: to ensure total comfort, we recommend it for 2/3 guests, but it is possible for up to 4 to stay. The kitchen is spacious and equipped; the bathroom, although small, is complete with everything. Free parking in front of the house, outside the Restricted Traffic Zone (ZTL).

Location · Value · Cleanliness

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Value · Family · Checkout

Podere Piazza house with panoramic view

Podere Piazza is an estate, has its origin in the 15th century. The vacation home was built at the beginning of the 17th century. Podere Piazza was the residence of Alessandro Cervini degli Spannocchi, who was appointed Archbishop of Siena on May 29, 1747. He was a Nobile di Montepulciano and Patrizier of Siena. The buildings of Podere Piazza still bear his coat of arms today. This also explains our little church, at the road junction, in front of it to the right to the pine avenue and to the left into the driveway.

Family · Value · Accuracy

Private House for 4P – La Capanna Di Azzurra

Ideal for families, couples or friends looking for an elegant and welcoming home, this house is designed for those who want to experience the Tuscan countryside without sacrificing the comfort of the city. Imagine a breakfast looking at the profile of Siena, days between art, wine and nature, and the return at sunset, when the light warms the stone and the silence restores the authentic rhythm of these places. A practical, charming and scenic retreat, perfect for visiting Siena and its surroundings!

Value · Location · View

Charming Tuscan Villa with View forFamily&Friends

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Location · Value · Biking

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Family · Value · Decor

Capanna di Elfo - Capanna Di Elfo

Capanna di Elfo is a beautifully restored former Tuscan barn, carefully renovated by its owners Claudio and Angelica to create a welcoming countryside home that combines traditional character with modern comfort. Set in a small rural hamlet yet completely independent, the villa offers privacy, open views, and the peaceful atmosphere of the Tuscan countryside. Surrounded by a private garden, the property enjoys panoramic views across rolling hills and vineyards — the kind of landscape that ...

Location · Family · Parking

Apartment in historic Villa in Siena_"Il Campo"

The apartment "Il Campo" is part of "Villa il Borghetto - Apartments". Villa il Borghetto offers apartments in Siena in a historic Villa, with the guarantee of an authentic hospitality, thanks to the family management of the "landlords". Villa il Borghetto has been designed to accommodate families wishing to experience Siena as a local, offering a convenient location to visit Siena without giving up the view of the Typical Tuscany rolling hills and the convenience of a free private parking.

Location · Family · Walkability

Luxury Penthouse Overlooking Piazza del Campo

There are many houses in Siena. But very few can say they've been here. Overlooking the city’s most iconic square, this penthouse offers a rare experience: Wake up to the golden light caressing the Palazzo Pubblico and fall asleep above one of the most beautiful places in the world. The location is simply one of a kind. Just outside the door, you'll find yourself immersed in history, surrounded by restaurants, wines, and a timeless atmosphere.

Value · Family · Nearby

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Location · Value · Breakfast

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Value · Family · Heating

Strategic Apartment

A new renovated apartment, Perfect for who wants to visit siena and the countryside as well ( Chianti, Montalcino ecc). The historic city center reachable by car in 5 minutes. You can park your car at the gas station near the apartment. *** IF YOU DON’T HAVE A CAR, IT WOULD BE VERY INCONVENIENT.

Location · Family · Amenities