Vacation rentals in Colle Ciupi

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!

Location · Value · River

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 · Indoor spaces

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Family · Value · Laundry

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

Family · Value · View

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.

Value · Family · Check-in

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

Family · Location · Wifi

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Value · Location · Comfort

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Family · Value · Outdoor spaces

Il Vecchio Noce

In the ancient rural complex of Caggio, "Il vecchio noce" offers a fully renovated apartment (recently, this past winter 2025/26) that can accommodate 2 to 4 people. The complex is located in the heart of the Tuscan countryside, in the Sienese Montagnola area, near the medieval village of Monteriggioni and the route of the Via Francigena. The accommodation is called the "granaio" (barn) of the village, as it faces south and is on the ground floor.

Location · Family · Outdoor spaces

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Location · Value · Walkability

Terrace on the walls of Siena - Casa Laura

Elegant apartment in the center of Siena with a large terrace, 600 m from the stadium and 1 km from Piazza del Campo. Located on the 4th floor (elevator up to the 3rd), it offers 2 double bedrooms, 2 bathrooms, an equipped kitchen, air conditioning in every room and a beautiful panoramic terrace above the historic walls. In the limited traffic zone. Perfect for experiencing Siena in comfort!

Location · Family · Check-in

Countryside, 10 min from Siena

Apartment and large fenced garden for exclusive use. It's a must for countryside, peace and relaxation, close to major places of cultural interest, trekking, biking trails. In a hilly area characterized by beautiful oak and holm oak forests, it enjoys a quiet location and a beautiful view of Siena, which is only 7 km away. (2 km are dirt road).

Family · Location · View