Holiday rentals in Sestano

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, 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 seeking 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 · Amenities

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Location · Value · Decor

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.

Location · Value · Breakfast

Villa marielena chianti farmhouse with hot tub - v

Villa Marielena is a beautifully restored Tuscan farmhouse located in the prestigious Castel in Villa area of Gaiole in Chianti, one of the most renowned wine regions in Italy. Surrounded by vineyards and olive groves, the villa offers privacy, panoramic views, and direct access to the landscapes that make Chianti famous. The property enjoys a privileged position for exploring Tuscany’s wine country. The vibrant town of Castelnuovo Berardenga is only 8 km away, while Siena and many of ...

Family · Location · Kitchen

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

Family · Value · Pool

Bed and Breakfast Casa Cernano

- 5 Double or Triple rooms each with its own bathroom/WC, with individual entrances from the outside area - Rooms are also individually rented -The price of your stay is based on 1 double room each 2 guests ( also with separate beds upon request ) - Garden - Car park - Free Wi-Fi - Barn with sitting aerea, games for children, coffee machine, ping ong table - Breakfast sweet or savory upon request ( 5 or 7 euro a person/day ) - Dogs are welcome ( 15 euro the entire stay )

Value · Family · Amenities

Incredible Views & Pool in the Tuscan Hills

Escape to the heart of Tuscany and enjoy a stay surrounded by rolling hills, timeless beauty, and unforgettable views. The house offers access to a beautiful shared swimming pool and peaceful outdoor areas, perfect for relaxing in the sun or enjoying quiet evenings. Inside, you will find comfort, style, and everything you need for a memorable stay. Ideal for couples, families, or groups of friends looking for an authentic Tuscan experience just a short drive from Siena.

Location · Value · Amenities

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.

Value · Location · Decor

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Location · Family · Checkout

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Family · Location · Access

Independent "Chianti" double bedroom

Immersed in the renowned Sienese hills in a portion of a farmhouse dating back to 1921 and finely restored respecting the architecture and environment of the territory. Large double bedroom, bathroom with full shower, independent heating and independent entrance. 5 min drive from Castelnuovo Berardenga.

Location · Value · Amenities

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Location · Value · Biking