Holiday houses in San Donato

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Top-rated holiday rentals in San Donato

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Top Guest favourite

An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.

Condo in Noce

Historic 17th-century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. 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 with a wonderful view of the castle, hills, and vineyards with breathtaking sunsets.

FamilyValueQuiet

5.0 out of 5 average rating, 218 reviews

Top Guest favourite

Home in Greve in Chianti

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.

FamilyLocationLong stay

4.99 out of 5 average rating, 113 reviews

Top Guest favourite

An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.

Holiday home in Badia a Passignano

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

LocationValueHospitality

5.0 out of 5 average rating, 121 reviews

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

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.

FamilyLocationBathroom

4.98 out of 5 average rating, 54 reviews

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

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.

LocationValueLong stay

4.98 out of 5 average rating, 216 reviews

Guest favourite

Condo in San Donato

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.

ValueLocationAir conditioning

4.94 out of 5 average rating, 84 reviews

Top Guest favourite

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

LocationFamilyBackyard

4.98 out of 5 average rating, 105 reviews

Superhost

Home in Barberino Tavarnelle

Nada Home

3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

LocationValueBreakfast

4.87 out of 5 average rating, 215 reviews

Top Guest favourite

The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.

Home in Barberino Tavarnelle

Casa Al Poggio in Chianti Shire

Casa al Poggio is a 145 sqm Tuscan country house in the heart of Chianti. The ground floor features a large living area with a kitchen and fireplace. Upstairs are 2 double bedrooms and an open room with a versatile sofa bed (set up as a double or 2 singles). A relaxing bathroom offers a shower, bathtub, and Chianti views. Outside, a terrace in the gravel garden awaits for your evenings. Perfect for experiencing authentic Tuscany!

FamilyValueHospitality

4.96 out of 5 average rating, 330 reviews

Top Guest favourite

A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.

Villa in Tignano

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

LocationFamilyAccuracy

4.96 out of 5 average rating, 207 reviews

Top Guest favourite

Bright pink flowers frame a tranquil infinity pool, with rolling green hills visible in the background. The landscape is dotted with tall trees and stretches toward distant mountains under a clear blue sky.

Villa in Barberino Tavarnelle

Valluccia 51

Relax and recharge in this oasis of tranquillity and elegance. Casa Gioia is a farmhouse totally renovated and cared for every details, located between Florence and Siena, in the heart of Chianti, among vines and olive trees. The tranquillity and sounds of nature surround our structure equipped with all the comforts to offer our guests an unforgettably stay.

FamilyValueComfort

5.0 out of 5 average rating, 49 reviews

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

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) .

LocationFamilyLaundry

4.92 out of 5 average rating, 141 reviews