Search Monteriggioni villas and holiday homes

Castello La Leccia is a restored medieval hamlet with an 11th-century castle, located 2 kilometres from Castellina in Chianti, offering a unique and authentic Tuscan experience.
This farm stay features a restaurant serving traditional Tuscan cuisine, a swimming pool, a spa, and a terrace with panoramic views of the Chianti countryside, perfect for a relaxing escape.

This luxurious eight-bedroom villa is situated in the Tuscan countryside near Casole d'Elsa, approximately 30 km from Siena and San Gimignano.
The property boasts nine bathrooms, a heated infinity pool, a wood-fired pizza oven, and can comfortably accommodate up to 16 guests, offering convenient access to the medieval towns of Siena and San Gimignano.

Castel Pietraio is a restored medieval castle situated in the Tuscan countryside, just 10km from the walled village of Monteriggioni and less than 30km from Siena. The property has received very good user ratings, with excellent location and cleanliness ratings.
The castle offers a range of modern comforts within its historical setting, including a swimming pool, a jacuzzi, a tennis court, and a restaurant. Guests can enjoy a variety of activities such as horseback riding, walking, and cycling in the surrounding countryside.

This holiday home in Ripostena, near Casole d’Elsa, is situated approximately 35km from Piazza del Campo in Siena and 31km from Palazzo Chigi-Saracini.
The property boasts a swimming pool, fitness centre, and free Wi-Fi, plus bike rentals for exploring nearby cycling and hiking trails, offering mountain views from a private balcony.

Antico Borgo Poggiarello is located in the Chianti Hills, a short distance from Siena and Monteriggioni, surrounded by woods and vineyards. The property has received excellent ratings for location, cleanliness, and user experience.
The accommodation is set within a 17th-century village, featuring an ancient 9th-century tower with stunning views. Guests can enjoy a swimming pool, a spa, a restaurant, a bar, a fitness centre, and a thermal bath, as well as a range of other amenities and activities.

La Villetta dei nonni, a holiday home in Colle di Val d'Elsa, is conveniently located 24km from Siena's Piazza del Campo and within 38-48km of major Florentine attractions such as Piazza Matteotti, Piazzale Michelangelo, and the Pitti Palace.
This 110 square metre property sleeps up to 11 guests and boasts a private garden, air conditioning, a fully equipped kitchen with dishwasher, Wi-Fi, and parking, making it ideal for families.

Mulino Di Quercegrossa, in the Chianti region, offers a family-friendly farmhouse stay a 32km drive from Siena and 50km from Florence, boasting stunning views of the Chianti hills.
This one-bedroom property features seven interconnected outdoor pools, a restaurant serving modern Tuscan cuisine, a bar, room service, free Wi-Fi, and a fully equipped kitchen; guests can also enjoy the on-site garden and terrace.

Il Fortino, a holiday home in Monteriggioni, is conveniently located 11km from Siena’s Piazza del Campo, close to the historic walls.
This two-bedroom, two-bathroom property boasts a well-equipped kitchen, terrace, garden, and private parking; it sleeps up to four guests and offers a fireplace and scenic views.

Casa La Cedrina, located in Lornano near Monteriggioni, is approximately 16km from Siena's Piazza del Campo and 32km from Grosseto's Piazza Matteotti, offering easy access to these Tuscan cities.
This 200 square metre property boasts four bedrooms, three bathrooms, a private pool, and a garden, comfortably accommodating up to 15 guests and providing free Wi-Fi and parking.

Case Vacanza Podere Risoino is located in Poggibonsi, just 22 kilometres from Siena's Piazza del Campo and 32 kilometres from Lucca's Piazza Matteotti, offering a peaceful retreat in the Tuscan countryside. It has received very good user ratings and excellent ratings for location and cleanliness.
The property features a private pool with stunning views, a relaxing garden, and a fully equipped kitchen. Guests can also enjoy a private bathroom with a bidet, free Wi-Fi, free private parking, and easy access to nearby cities.

This family-friendly villa is located just outside Siena, within a 2km radius of the Siena Stadium and Palasport Mens Sana, offering a peaceful escape from the city centre. It has received excellent ratings for user experience, location and cleanliness.
This five-bedroom property sleeps up to 10 guests and features a well-equipped kitchen, a private pool, a garden, a terrace, a spa, a tennis court and parking. You can enjoy a relaxing dip in the pool, a game of tennis, or a spa treatment, all within the comfort of your own private accommodation.

This Poggibonsi dwelling offers a strategic Tuscan base, located 350 metres from the Siena Eye Laser clinic and 13 kilometres from San Gimignano.
This 33 square metre apartment accommodates up to five guests, featuring one bedroom, one bathroom, and a fully equipped kitchen, with air conditioning and parking provided.

Borgo Campassini farmhouse is situated near Monteriggioni, Tuscany, 19 kilometres from Siena’s Piazza del Campo and 39 kilometres from Grosseto’s Piazza Matteotti, offering stunning garden views of the Tuscan countryside and proximity to the medieval walls and towers.
This family-friendly property features air-conditioned apartments with fully equipped kitchens (including fridges and dishwashers), private bathrooms, a swimming pool, free Wi-Fi, and free private parking; bed linen and towels are provided.

Villa Anna is situated in Colle di Val d'Elsa, a town in the Tuscan hills, just 27 kilometres from Siena's Piazza del Campo and 42 kilometres from Piazza Matteotti.
This two-bedroom villa offers a peaceful garden, a terrace for outdoor dining and a fireplace, perfect for relaxing after exploring the region.

Villa La Petrosa, a 200 square metre, five-bedroom farmhouse in Radda in Chianti, offers easy access to the Chianti Classico wine region and its cultural attractions.
This pet-friendly property boasts a private pool, extensive gardens, three bathrooms, and can comfortably accommodate up to eleven guests, featuring a well-equipped kitchen and multiple balconies.

Fattoria di Corsignano is located in the Chianti wine area, just 10km from Siena and a short drive from Castelnuovo Berardenga, offering a peaceful escape in the Tuscan countryside. The farm consistently receives very good ratings for location, cleanliness, and overall experience.
The property comprises three separate country houses, each with its own entrance and parking, offering a variety of rooms and apartments. Guests can enjoy a range of amenities, including a swimming pool, a restaurant serving traditional Tuscan cuisine, and activities like wine tasting, cooking classes, and bike rentals.