Holiday houses in Casole d'Elsa

Casa al Gianni - The Simignano Barn

Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and 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, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

Family · Location · Checkout

Holiday House "Anna" - the MUSICIAN for 4-5 persons

"the MUSICIAN" IS located IN the historic center, inside a house from 1400 IS near Siena, Florence, San Gimignano, Volterra, and the Chianti area. Suitable for those who love the countryside, but want the advantages offered by a country with all the services: shops,restaurants,bars,post office,bank,pharmacy,church, tourist office, museum. Live the summer experience of a country that alternates its tranquility with moments animated by parties,markets,music and the tradition of the Palio (on the 2nd Sunday of July).

Location · Family · Hospitality

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

Location · Value · Condition

Casa Panorama

Welcome to Casa Panorama! A cozy apartment situated in the wonderful Tuscan countryside just a stone's throw away from the medieval town of Casole d'Elsa.Casa Panorama is in between some of the most beautiful locations such as Siena,Monteriggioni,Florence,San Gimignan,Volterra and many other hidden hilltop Tuscan jewels.Our house is situated less than 1 km from the center of the very romantic town of Casole d'Elsa where there are restaurants and much to see as far as culture and art is concerned

Family · Location · Accuracy

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Value · Location · Cleanliness

Dimora San Donato - Apt.1985

Dimora San Donato, located in the historic centre of Casole d'Elsa, combines refinement and elegance. The interiors, spacious with great attention to detail, offer a perfect blend between tradition and modernity. The location allows guests to immerse themselves in the daily life of the village, surrounded by a breathtaking landscape of rolling hills and centuries old cypresses. The Dimora represents a journey into the heart of Tuscany, where history, culture and natural beauty come together.

Family · Location · Nearby

Stone cottage + private garden + scenic pool

✅ 80 m² on 2 floors. Equipped kitchen ,1 double bedroom and 1 bedroom with 2 twin beds both with airco, 2 full bathrooms. Patio ideal for morning coffee and relaxing evenings under the stars ✨✨ ✅ Unique panoramic views from the pool ✅ 1 km easy walking to the medieval town Casole with cobblestone streets and delightful restaurants ✅ Perfect central location to visit hidden gems + Unesco Heritage Sites Noce Cottage is part of Monti 1824 farmhouse ,composed of 6 accommodations + pool

Value · Family · Walkability

Mirella apartment in the historic center

Comodo appartamento per 2-4 persone, in centro storico a Casole d’Elsa, con vista panoramica dalla terrazza sulle colline toscane. A 18 km da San Gimignano, 25 km da Volterra e 35 km da Siena. L’alloggio offre due camere, una matrimoniale e una doppia con letti singoli, bagno con doccia, sala da pranzo con divano e tv, cucina, terrazza, cantina, Wi-Fi, stanzino esterno con lavatrice. Parcheggio gratuito a 2 e 5 minuti a piedi, concesso il carico e scarico. CIN: IT052004C2R23DIUHK

Family · Location · Indoor spaces

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.

Family · Value · Outdoor spaces

Manuela apartment with pool in farmhouse

You will be staying in an apartment located on the first floor, with a separate entrance and accessed by climbing 17 steps. It consists of a kitchen, two bedrooms (one double and one with two single beds), a bathroom with a shower, and mosquito nets on the windows. Small shared balcony with the GIRASOLI apartment. YOU MUST PAY THE TOURIST TAX AT CHECK-IN: €1 per person for the first 5 days. Heating allowed from 1 November to 15 April (Regional Law) €20.00 per day

Location · Family · Hospitality

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Location · Family · Walkability

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 · Wi-Fi