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Holiday houses in San Donato

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Top-rated holiday rentals in San Donato

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 110 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 137 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 337 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Top Guest favourite
A scenic view is framed by an arched window, showcasing rolling hills and rooftops of the town. Green plants in pots add a touch of nature, enhancing the tranquility of the surrounding landscape under a clear sky.
Condo in San Donato
4.98 out of 5 average rating, 54 reviews

SAN DONATO IN POGGIO Duplex Penthouse

Enchanting penthouse duplex flat in the heart of the medieval town of S. Donato in Poggio, 418 meters above sea level. The original stone steps , 40 STEPS TO THE APARTMENT, of the 10th Century building brings you to a sprawling view of the town and the glorious Chianti hills. The building is part of the the original town walls and only steps from one of the two arches which were once the two doors to access the village. Porta Sense facing Siena, Porta Fiorentina facing Florence.

Top Guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 240 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a commanding position with an amazing view, where you can enjoy breathtaking sunsets. The complete privacy of the house, the cozy garden, and the large loggia allow you to enjoy your stay in total tranquility. Our reviews are your best guarantee.

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 345 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Top Guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 215 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Guest favourite
Condo in San Donato
4.94 out of 5 average rating, 83 reviews

Apartment Fiorenza in Chianti Classico

Appartamento Fiorenza is a delightful two-room apartment located on the ground floor of an ancient residence, on the main street of the fortified village of medieval origin of San Donato in Poggio, in the heart of Chianti Classico, 30 minutes from Florence and Siena and from San Gimignano and Volterra. The village, among the most beautiful in Italy, is characterized by narrow streets paved in stone and crossed by small bridges that allowed the guard troops access to the Walls.

Guest favourite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Welcome to one of the most exclusive residences in Chianti: a medieval tower transformed into a refined luxury retreat overlooking the Tuscan hills. Contemporary design, iconic furnishings, works of art and luxury comforts come together in a unique experience. An oasis of tranquility with a private garden, glass annex, Wi-Fi, and smart working area. Extra services: private chef, tastings in the cellar, wellness treatments and tours of the most beautiful villages in Tuscany.

Guest favourite
A cozy terrace features two green chairs adorned with tropical-patterned cushions. A small round table sits between them, while a collection of potted plants adds greenery. The rustic stone walls and tiled roofs of neighboring buildings can be seen, illuminated by soft lighting from the setting sun.
Apartment in San Donato
4.93 out of 5 average rating, 57 reviews

Your home in Chianti

A charming apartment in the village of San Donato in Poggio, furnished in a vintage style with the aim of making you feel at home. For those who want to get lost in Tuscan vineyards and villages, this location allows you to enjoy Chianti to the fullest, reaching the main tourist destinations: San Gimignano, Volterra, Monteriggioni and many other villages, Florence and Siena are 30 minutes away, the sea and the mountain can be reached in just over an hour.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 476 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Guest favourite
A large shared pool is set against a backdrop of rolling hills and open skies. Several lounge chairs are arranged around the pool, offering a space for relaxation. The clear turquoise water reflects the surrounding landscape and clouds above.
Apartment in Badia a Passignano
4.92 out of 5 average rating, 140 reviews

Chianti, Country house with pool

Peace and relax in the heart of Chianti between Florence and Siena, close to Badia a Passignano (4 km dirt road not too much easy if you drive a sportive car) . In an old farmhouse complex, the apartment "Sangiovese" was recently restored by retrieving the characteristics of the Tuscan rural tradition. Large shared pool (01/05 - 30/09) .

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