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This Radda in Chianti holiday home is situated 2.3km from Castello di Radda winery and 4.3km from Castello di Albola, with other vineyards within a 15km radius.
The 85 square metre property offers three bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a terrace, garden, and parking.

This five-bedroom country house, a restored 16th-century oratory, enjoys a hilltop position near Castellina in Chianti, offering panoramic views of the Sienese Chianti countryside and the towers of Monteriggioni, with Castellina 5km, Poggibonsi 15km, Siena and San Gimignano 20km, and Florence 50km away.
The 400-square-metre property, comprising a main house and annex, sleeps ten guests and includes a private 7m x 14m swimming pool, a fully equipped kitchen, five bathrooms, and extensive grounds within a 460-hectare estate encompassing vineyards, olive groves, and wheat fields.

This Portoferraio holiday home is situated within 3.2km of Biodola Beach, Spiaggia di Scaglieri, and the Arcipelago Toscano National Park, also conveniently close to the Golf Club Hermitage.
The 150 square metre property sleeps six guests in three bedrooms and two bathrooms, boasting a private terrace, garden, tennis court, and parking, plus a fully equipped kitchen and air conditioning.

This Castelnuovo Berardenga holiday cottage is situated 4.3 km from the Villa a Sesta Polo Club and within 15 km of Piazza Marconi and the Vittorio Alfieri Theatre, offering easy access to local attractions.
The 38-square-metre property features one bedroom, one bathroom, sleeps two guests, includes a private pool, parking, air conditioning, and a fully equipped kitchen with a refrigerator.

This one-bedroom cottage is situated on the banks of a river, just 1.1 kilometres from the Arno River and 3.7 kilometres from the iconic Leaning Tower of Pisa. The cottage offers a private, fenced garden, a fully equipped kitchen with a fridge, and a terrace or balcony, perfect for enjoying the peaceful surroundings.

Tenuta La Fuga is located in the Tuscan countryside, just 41 kilometres from Siena and a short distance from the charming town of Montalcino, renowned for its Brunello di Montalcino wine. This property has received excellent guest reviews, making it a popular choice for visitors to the area.
This 3-bedroom, 2-bathroom cottage offers 120 square metres of space, comfortably accommodating up to 6 guests. The cottage features a private swimming pool, a spacious terrace with stunning views, a fully equipped kitchen, air conditioning, and a tranquil garden, perfect for relaxing and enjoying the Tuscan countryside.

This Castelnuovo Berardenga holiday cottage is situated 4.3 km from the Villa a Sesta Polo Club and within 15 km of Siena's Piazza Marconi and Vittorio Alfieri Theatre, offering easy access to Tuscan attractions.
The 35-square-metre property features one bedroom, one bathroom, sleeps two guests, and includes air conditioning, a swimming pool, a garden, and parking.

This 17th-century Tuscan farmhouse, offering a romantic escape for two, is located in the countryside near Asciano, approximately 32 kilometres from the Val d'Orcia and a short drive from Montalcino, Buonconvento, and Siena.
This family-friendly cottage boasts air conditioning, a private swimming pool (May-September), a garden, and shared outdoor facilities including a barbecue, ping pong, foosball, and a bocce court, with internet access provided.

This charming cottage is situated in a peaceful rural setting, just 9 miles from the historic landmarks of Fattoria Sardigiustiniani s.s.a, Piazza Santa Maria, and Porta Santa Maria, offering easy access to the area's attractions. The property has received excellent ratings for its cleanliness, location, and overall experience.
The cottage spans 52 square metres and comfortably sleeps four guests in one bedroom and one bathroom. Guests can enjoy a private pool, outdoor spa tub, and a tranquil garden, as well as modern amenities like free Wi-Fi, a fully equipped kitchen, and a washing machine.

This house is situated in San Quirico, just 19 kilometres from Montecatini Train Station and 10 kilometres from San Domenico, offering a peaceful escape in the Tuscan countryside. The property has received very good ratings for its location and overall experience, as well as a good rating for cleanliness.
The house features a private garden and terrace, perfect for enjoying the warm Italian weather. Guests can take advantage of the fully equipped kitchen, relax in the hot tub or swim in the private pool.

Cottage La Vita is located in a neighbourhood on the northern outskirts of Siena, just 12 kilometres from the medieval walled town of Monteriggioni and within easy reach of other Tuscan gems like Florence (60 kilometres) and San Gimignano (30 kilometres).
This two-bedroom, two-bathroom property can accommodate up to six guests and features a private swimming pool, hot tub, and outdoor dining area, perfect for relaxing and enjoying the Tuscan sunshine.

This Colle di Val d'Elsa holiday cottage, a 15-minute walk from a tennis court and near the Museo del Cristallo and Colle di Val d'Elsa Cathedral, offers easy access to local attractions.
The 50 square metre self-catering property sleeps two, features a living room, kitchen, bedroom, bathroom, dedicated workspace, and permits up to three pets (fees apply); a cot and high chair are available for hire.

This Montelupo Fiorentino holiday home is conveniently located a short drive (approximately 4.3km) from the Arno River and 6.8km from the Stadio Carlo Castellani.
The 93 square metre property sleeps six guests in two bedrooms and two bathrooms, boasting a private garden with a fire pit, swimming pool, jacuzzi, and a fully equipped kitchen including a dishwasher.

Cottage Violapo offers a peaceful rural escape in Civitella Paganico, located in open countryside near Roccastrada, a town notable for its unique geological setting on trachytic rock.
This 130 square metre holiday home accommodates up to eight guests across three bedrooms and three bathrooms, featuring air conditioning, a private garden, swimming pool, jacuzzi, and Wi-Fi.

Cottage Monti Pet Friendly Shared Pool is a centrally located cottage in Casole d'Elsa, offering convenient access to explore the neighbourhood and nearby landmarks.
This accommodation for two guests allows pets and features a garden, parking, air conditioning, a kitchen with a fridge and microwave, and a shared outdoor swimming pool with a barbeque area.

This Buti holiday home is situated within 10km of Rocca di Vicopisano, the Arno River, and Bientina Town Hall, and 14km from the Piaggio Museum and Piscina Comunale Pontedera.
Sleeping five guests, this three-bedroom property boasts two bathrooms, a fully equipped kitchen with dishwasher, a private swimming pool, hot tub, barbecue, and parking; enjoy the fireplace and Smart TV after exploring the local historical landmarks.