• Apartments: 6
• Sleeps: 20
• Location: Gaiole in Chianti (Countryside)
• Daily price: From € 80 to € 230

The warm hospitality of this estate creates an environment where holiday goers can enjoy the Tuscan styled vacation rentals, panoramic vistas, a lovely private pool & romantic spa. Spacious apartments in the heart of Chianti, close to Siena & Arezzo.

• Apartments: 5
• Sleeps: 24
• Location: Monteroni d'Arbia (Countryside)
• Weekly price: From € 500 to € 1200

A charming rural home with pool and a great view on the unspoilt nature of the Crete Senesi, just 10 km south of Siena near the Val d'Orcia. It of five spacious, independent apartments with all modern amenities.

• Rooms: 4
• Sleeps: 8
• Location: Monteroni d'Arbia (Countryside)
• Weekly price: From € 2100 to € 3600

Charming villa with private pool, garden and BBQ area in the enchanting landscape of the Crete Senesi near Siena. It offers 4 bedrooms and 3 bathrooms located on two floors overlooking the marvelous Tuscan countryside. A B&B only in mid & low season.

• Apartments: 5
• Sleeps: 21
• Location: Monteroni d'Arbia (Countryside)
• Daily price: From € 800 to € 900
• Weekly price: From € 5600 to € 6300

Cozy & comfortable, the large vacation villa at San Fabiano can host up to 21 guests and features the best of Tuscany all in one place! The villa is just 20 minutes south of Siena.

• Apartments: 9
• Sleeps: 27
• Location: Casole d'Elsa (Countryside)
• Daily price: From € 100 to € 328
• Weekly price: From € 600 to € 1200

The picturesque setting of these vacation apartments promise stunning scenery, sunsets, outdoor picnics and afternoons by the pool. Great base for your vacation: visit Chianti, Siena, Volterra and Florence.

• Apartments: 6
• Sleeps: 26
• Location: Casole d'Elsa (Countryside)
• Daily price: From € 60 to € 215

A beautiful family run estate with self catering apartments & independent vacation villas. Located in the heart of the Siena landscape, it promises panoramic views & tranquility while within walking distance of shops & restaurants.

• Apartments: 4
• Sleeps: 12
• Location: San Gimignano (Countryside)
• Daily price: From € 60 to € 140
• Weekly price: From € 420 to € 1190

The four lovely vacation rental apartments at this farmhouse overlook the fabulous tower town of San Gimignano. Combine lovely views, fresh air and the beauty of the landscape on your vacation in Tuscany.

• Apartments: 4
• Rooms: 1
• Sleeps: 18
• Location: San Gimignano (Countryside)
• Daily price: From € 95 to € 340
• Weekly price: From € 630 to € 2380

The 5 accommodations in this luxurious, recently renovated farm estate offer comfort & style. Perfect for couples, families & small groups, they offer a magic place in the heart of Tuscany, with panoramic pool and breathtaking views.

• Apartments: 2
• Sleeps: 6
• Location: Gaiole in Chianti (Countryside)
• Daily price: From € 180 to € 300

This beautiful farmhouse near Gaiole in Chianti features 2 holiday rental villas for families & friends exploring Tuscany. Great views, a Tuscan atmosphere, attentive service & homey comforts for a tranquil vacation.

• Rooms: 5
• Sleeps: 10
• Location: Pienza (Countryside)
• Weekly price: From € 3400 to € 6800

This enchantingly simple yet graceful vacation villa rental only minutes from the historic town of Pienza features an ideal holiday accommodation for up to 10 persons. Private pool, WiFi, air conditioning and fabulous views.

• Apartments: 3
• Sleeps: 10
• Location: Sinalunga (Countryside)
• Daily price: From € 60 to € 200

Set in the countryside of Siena, between the Crete Senesi and the Val d'Orcia, the villa offers 3 cozy and romantic self-catering apartments and a beautiful outdoor pool. It's a great base to explore central and southern Tuscany and Umbria.

• Rooms: 4
• Sleeps: 8
• Location: Castiglione d'Orcia (Countryside)
• Daily price: From € 150 to € 170

Four elegant B&B suites with king size beds at BelSentiero provide an intimate setting for a holiday vacation exploring the beautiful UNESCO Heritage scenery in Val d’Orcia with spacious gardens, veranda & Tuscan hospitality.

• Rooms: 11
• Location: Sovicille (Countryside)
• Daily price: From € 72 to € 90

This vacation home situated a few km from Siena offers charming rooms furnished in typical Tuscan style, a huge outside pool overlooking panoramic views on the surrounding hills, homemade breakfast and a Tuscan restaurant also serving pizza.

• Rooms: 2
• Sleeps: 6
• Location: Radda in Chianti (City)
• Daily price: From € 89 to € 153

Enjoy the beauty of Tuscany from this stunning position above the historic town of Radda in Chianti. The Art Rebus Tower features two double bedrooms in the center of a quaint medieval hamlet nestled among the vineyards between Florence & Siena.

• Apartments: 4
• Rooms: 4
• Sleeps: 15
• Location: Colle di Val d'Elsa (Countryside)
• Daily price: From € 89
• Weekly price: From € 547 to € 1070

A wonderful ancient Romanesque church converted in a beautiful vacation home and immersed in the unspoilt nature of Chianti. It consists of 4 wide and fully equipped apartments with pool for an unforgettable stay amidst the Tuscan gentle hills.