• Apartments: 1
• Rooms: 24
• Sleeps: 48
• Location: San Casciano in Val di Pesa (Countryside)
• Daily price: From € 80 to € 400

This villa hosts B&B accommodation in a stunning location, surrounded by the marvelous vineyards of Chianti. It offers spacious and romantic rooms with all comforts, a restaurant specialized in organic meals, a Spa and swimming pool.

• Apartments: 9
• Sleeps: 26
• Location: Montespertoli (Countryside)
• Weekly price: From € 530 to € 1220

Stone villa from the 13th century offers apartments for your vacation in the Chianti hills near Florence. Managed directly by the owners, guests receive personal attention and service while enjoying the self-catering accommodation and the villa's pool.

• Apartments: 22
• Sleeps: 100
• Location: Gambassi Terme (Countryside)
• Daily price: From € 86
• Weekly price: From € 590

The Tuscany hamlet Borgo della Meliana holiday accommodations for the perfect holiday setting for families, friends & destination wedding or events. Elegant decor, green gardens, panoramic pool & so much more

• Rooms: 9
• Sleeps: 17
• Location: Montaione (Countryside)

Villa Piaggia, located in Montaione near San Gimignano, is an exclusive and elegant villa that can host up to 17 guests. The villa and its swimming pool is surrounded by a large park and vineyards, enjoying a beautiful view over the Tuscan countryside.

• Rooms: 3
• Sleeps: 6
• Location: Vinci (Countryside)

The elegant wine resort near Vinci offers rooms in a beautiful Medicean villa, surrounded by gorgeous gardens and vineyards. New pool and restaurant, wine cellar visits and tastings make the estate perfect base for enjoying Tuscany.

• Rooms: 7
• Sleeps: 14
• Location: Poggibonsi (Countryside)

Villa Vianci is a family-run holiday villa rental between the hills of Chianti and the historic city of Siena. The beautiful garden offers a large pool, lots of space throughout the villa for up to 14 guests on holiday in Tuscany.

• Sleeps: 12
• Location: Castelfiorentino (Countryside)

An ancient castle sitting on the gentle hills of Chianti, finely restored and turned into a beautiful luxury villa perfect for 12 people. It offers a private, gorgeous outdoor pool and exclusive services to make your stay unforgettable.

• Apartments: 1
• Rooms: 3
• Sleeps: 12
• Location: Tavarnelle Val di Pesa (Countryside)
• Daily price: From € 180 to € 300

Lush gardens, charming decors & panoramic views. This prestigious medieval Villa has been totally restored for your holiday near Chianti & Florence. It offers two perfect solutions: 4 charming B&B rooms or the entire villa for a deluxe holiday.

• Apartments: 2
• Sleeps: 6
• Location: San Casciano in Val di Pesa (Countryside)
• Daily price: From € 90 to € 300
• Weekly price: From € 630 to € 2100

The vacation apartments at Agriturismo La Canigiana are positioned in a panoramic position just outside of Florence. Cozy & comfortable, these self-catering apartments are for up to 3 persons each, share a lovely pool, WiFi & easy access to day trips.

• Apartments: 8
• Sleeps: 40
• Location: Certaldo (Countryside)
• Daily price: From € 106 to € 533
• Weekly price: From € 650 to € 3200

The eco-sustainable vacation accommodations of this Wine Resort combine the beauty of the Tuscan landscape near Certaldo with delicious wine, modern luxuries, comfortable holiday apartments & a vacation villa rental for up to 10 persons.

• Rooms: 4
• Sleeps: 10
• Location: Figline Valdarno (Countryside)
• Weekly price: From € 1400 to € 3200

Spacious & luminous Villa for 10 persons with a private panoramic pool and luxury decor, is in a prime position between Florence & Chianti. Easy access to Siena, Pisa and relaxing spa services.

• Sleeps: 4
• Location: Gambassi Terme (Countryside)
• Weekly price: From € 750 to € 980

A one bedroom private villa rental for vacation near San Gimignano and Chianti, promises tranquility, comfort & romantic Tuscan landscapes for your holiday. Perfect base also for a honeymoon.

• Apartments: 8
• Sleeps: 36
• Location: Certaldo (Countryside)
• Daily price: From € 55 to € 135

The family & pet-friendly vacation apartments La Certaldina provide the perfect relaxing atmosphere for a holiday in Tuscany. Enjoy the views, the pool, the food & wine while staying close to Certaldo, Florence & Chianti.

• Apartments: 2
• Sleeps: 11
• Location: Gambassi Terme (Countryside)

Surrounded by nature and gorgeous gardens with swimming pool, the villa's two apartments are ideal for a group of up to 11 guests wishing an exclusive stay in Tuscany. The location is very central, ideal for day trips to explore the region.

• Rooms: 6
• Sleeps: 12
• Location: San Casciano in Val di Pesa (Countryside)
• Weekly price: From € 670 to € 4000

Combine the exhilarating experience of Tuscan art, food & wine with the breath taking views of Chianti at this beautifully restored holiday villa for up to 12 persons in luminous spacious accommodations.