• Rooms: 3
• Sleeps: 5
• Location: Siena (City,Countryside)
• Weekly price: From € 2000 to € 5000

Perfect base for exploring Siena and the Tuscan countryside, the villa for 5 guests offers exclusive pool, tennis court, spacious gardens and olive tree orchard just outside Porta Romana and a 15 min walk to Piazza del Campo, heart of Siena.

• Rooms: 4
• Sleeps: 8
• Location: Monteroni d'Arbia (Countryside)
• Weekly price: From € 2700 to € 3980

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.

• 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.

• Apartments: 6
• Sleeps: 27
• Location: Cetona (Countryside)
• Weekly price: From € 500 to € 3000

A privately owned medieval village surrounded by woods in southern Tuscany has been restructured to offer both apartments and villas for families and small groups of friends searching for a unique vacation in Tuscany's countryside.

• Apartments: 5
• Rooms: 9
• Sleeps: 18
• Location: Monticiano (Countryside)
• Weekly price: From € 8200 to € 8550

This villa right outside the small town of Monticiano near the Abbey of San Galgano is ideal for weddings & special events. The villa with pool can host up to 18 guests and is just 25 minutes from Siena.

• Rooms: 7
• Sleeps: 14
• Location: San Gimignano (Countryside)
• Weekly price: From € 5800 to € 6490

This romantic Villa promise tranquility & spectacular views of San Gimignano & the Tuscan landscape. The villa can accommodate up to 14 guests and offers all best modern facilities; it has also a beautiful panoramic pool.

• Rooms: 5
• Sleeps: 10
• Location: Pienza (Countryside)
• Weekly price: From € 4000 to € 10000

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: 21
• Location: San Casciano dei Bagni (Countryside)
• Daily price: From € 180 to € 550

Luxury vacation villa rentals - a whole villa and 2 apartments - in southern Tuscany assure you of comfortable accommodations & beautiful day trips in Italy. The warm, friendly atmosphere, private pools and many amenities will create special memories.

• 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: 17
• Location: Siena (City)
• Daily price: From € 81 to € 199

Set in an elegant 19th century villa, this 3 star hotel is less than 10 minutes walking distance from Piazza del Campo. The hotel offers charming rooms overlooking the beautiful well-cared garden of the villa and free WiFi.

• Rooms: 6
• Location: Siena (Countryside)
• Daily price: From € 95 to € 179

This farmhouse is located in the countryside near Siena, close to the Chianti region. It has nice and comfortable apartments that are finely furnished in typical Tuscan style.

• Rooms: 26
• Location: Castelnuovo Berardenga (Countryside)
• Daily price: From € 162 to € 999

Borgo Villa Curina is a nice resort near Siena, in Castelnuovo di Berardenga. It offers elegant rooms with antiques and precious fabrics, as well as pool and tennis court.

• Rooms: 15
• Location: Colle di Val d'Elsa (City,Countryside)
• Daily price: From € 51 to € 225

This elegant villa is located near Colle Val D'Elsa. It is surrounded by a pleasant garden with outdoor pool. Rooms are tastefully furnished and equipped with modern comforts.

• Rooms: 37
• Location: Poggibonsi (City,Countryside)
• Daily price: From € 69 to € 254

This luxury hotel in the Chianti region near Poggibonsi offers elegant rooms equipped with major comforts. Set in 15th century villa it offers many facilities for its guests, such as pool, Jacuzzi and tennis court.

• Rooms: 13
• Location: Gaiole in Chianti (Countryside)
• Daily price: From € 139 to € 250

This wine resort in Chianti is located in beautiful Gaiole in Tuscany. It is set in ancient and carefully restored abbey equipped with modern comforts.

• Rooms: 17
• Location: Poggibonsi (City,Countryside)
• Daily price: From € 61 to € 110

Recently refurbished, this nice villa is located in Chianti. It offers nice and comfortable rooms and outdoor pool.

• Rooms: 18
• Location: Casole d'Elsa (Countryside)
• Daily price: From € 65 to € 390

Borgo Al Cerro offers fully furnished and equipped apartments, as well as a nice swimming pool. It is located near Casole D'Elsa, surrounded by Tuscan countryside.

• Rooms: 12
• Location: San Gimignano (City,Countryside)
• Daily price: From € 95 to € 150

Set in 18th century villa, Hotel Villa Belvedere is a family-run accommodation in San Gimignano. Locates just 10 minutes walking form the center it offers the luxury of a villa and the comforts of an hotel.

• Apartments: 6
• Rooms: 1
• Sleeps: 34
• Location: Sinalunga (Countryside)
• Daily price: From € 583

Immersed in the green hills between Siena and the Valdorcia, this attractive estate offers guests a large villa and characteristic apartments of various sizes for their holiday in Tuscany. It also has a beautiful park, outdoor pool and tennis court.

• Rooms: 96
• Location: Chianciano Terme (City,Countryside)
• Daily price: From € 43 to € 130

Located near the city center, this 3 star hotel offers large and quiet rooms. It is equipped with wellness center, business center, as well as restaurant and bar.