Search Certaldo villas and holiday homes

Agriturismo 'Podere Galieni' is an elevated property in Certaldo, offering panoramic countryside views and situated 4 kilometres from the town centre, with San Gimignano 15 kilometres, Volterra 30 kilometres, Siena 35 kilometres, and Florence 40 kilometres away.
This spacious 250 square metre holiday cottage, renovated in 2025, accommodates up to 16 guests across 6 bedrooms and 8 bathrooms, featuring air conditioning, WiFi, a private swimming pool (seasonal April-October), and a terraced garden with local farm produce sales.

Capanna 1826 is a San Gimignano farm stay, approximately 37 kilometres from Piazza Matteotti and 43 kilometres from the Pitti Palace in Florence, offering city views.
This one-bedroom, one-bathroom property features free Wi-Fi, private parking, room service (including wine delivery), a terrace, garden, and shared lounge, perfect for a relaxing stay.

This San Gimignano holiday home, 7km from the medieval town, enjoys a convenient location midway between Siena and Florence, ideal for exploring Tuscany.
The 90 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a private garden with barbecue, shared swimming pool, and high-speed Wi-Fi.

Farm listing for up to 4 people with an excellent rating of 90% based on 3 reviews. This accommodation is located in Castelfiorentino.
Facilities and services: a dish washer, a wheelchair friendly access and a fridge. This accommodation in Castelfiorentino has a swimming pool!

A Casa di Franca Villa con piscina is located in Gambassi Terme, a charming town in the Tuscan countryside, just 47 km from Florence. This villa has received excellent ratings for its location, cleanliness and overall experience.
The villa is a spacious 223 square metre property with 4 bedrooms, 3 bathrooms and can accommodate up to 24 guests. The villa features a private garden with a swimming pool, a fully equipped kitchen, air conditioning, free Wi-Fi and parking, plus barbecue facilities and is accessible for guests with disabilities.

This historical property is located in a residential district of Ponteginori, 120 metres from local amenities, 7 kilometres from Casino di Terra, and 10 kilometres from Montecatini Val di Cecina.
This 200 square metre villa accommodates up to 11 guests across four bedrooms, featuring a private garden with a seasonal swimming pool, a Jacuzzi, WiFi, and is situated 25 kilometres from the sandy beach at Marina di Cecina.

A Casa di Franca Villa con piscina, a spacious 223m² holiday home, is situated in the Chianti hills near Gambassi Terme, Tuscany, offering easy access to Tuscan vineyards.
This four-bedroom, three-bathroom villa sleeps up to 14 guests, boasting a private 5m x 14m swimming pool (open May 1st to October 15th), a fully equipped kitchen, air conditioning, Wi-Fi, and free baby equipment (on request).

Villa Arnilù is situated in San Gimignano, just 40 kilometres from both Piazza del Campo in Siena and Piazza Matteotti in San Gimignano, offering easy access to explore the region's historic gems. This spacious property provides ample room for a large group, with 8 bedrooms and 8 bathrooms across its 287 square metres, comfortably accommodating up to 32 guests.
The villa boasts a range of amenities to enhance your stay, including a private garden, a swimming pool, and barbecue facilities for al fresco dining. Guests can also enjoy the convenience of a fully equipped kitchen, free Wi-Fi, and on-site parking.

Villa Il Frantoio, situated in the Montespertoli countryside, 20km from Florence and within easy reach of Siena (65km) and Pisa (55km), offers a tranquil Tuscan escape.
This 60 square metre property features one bedroom, one bathroom, sleeps four, and includes a private terrace, swimming pool (June-September), tennis court, and access to the estate's wine cellar and olive oil tasting.

This spacious villa is situated in Gambassi Terme, Tuscany, 1.9km from Agricola Tamburini Emanuela and within 9.7km of Teatro del Popolo and Palazzo Pretorio.
The 223 square metre property boasts four bedrooms, three bathrooms, sleeps twelve guests, and includes a private pool, garden, parking, and a fully equipped kitchen with dishwasher.

Villa La Rosa, a semi-detached villa near Montelupo Fiorentino, is situated 2km from the town centre, 22km from Florence, and 60km from Pisa, offering easy access to major Tuscan destinations.
This 250 square metre, six-bedroom property sleeps 13 guests and boasts a private 2000m² terraced garden with a seasonal swimming pool (May 3rd - September 20th), a jacuzzi, and amenities including a barbecue, table tennis, and basketball.

This elevated cabin, situated amongst lavender fields, offers panoramic sunset views over Tuscan hills and vineyards, located a short drive from the UNESCO World Heritage medieval village of San Gimignano.
This secluded suite accommodates four guests with two bedrooms and one bathroom, featuring a private 40 sqm deck, a shared infinity pool, and in-room breakfast service for a tranquil Tuscan escape.