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Looking for a holiday of complete freedom in Chianti? A vacation home in Chianti will grant you great privacy and freedom, so you'll never be in a hurry for having to follow some kind of schedule. You will have at your disposal your own home in Chianti, one of the most beautiful and famous areas of Tuscany, amidst the wonderful countryside between Florence and Siena.

15 Properties Found


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Romitorio di Serelle

Relaxing Tuscany Farmhouse Apartments in Chianti

  • apartments: 15
  • sleeps: 68
  • Location: Barberino Val d'Elsa (Countryside)
  • weekly price: from € 700 to € 2050

The farmhouse is located in the heart of Chianti and offers 15 apartments furnished in traditional Tuscan style and provided with all of the main services and comforts. Large swimming pool and restaurant at guests' disposal.

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Tenuta Quadrifoglio

Vacation Apartments & B&B Tenuta Quadrifoglio: Florence & Siena

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  • apartments: 14
  • rooms: 5
  • Location: Gambassi Terme (Countryside)
  • daily price: from € 90 to € 270
  • weekly price: from € 850 to € 1650

The comfortable and kid friendly environment at Tenuta Quadrifoglio between Florence & Siena is an ideal destination for families, group events & destination weddings. A large garden & common room offer space & modern amenities. Book direct with Owner.

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Villa Le Torri

Holiday Apartments in Chianti Villa

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  • apartments: 9
  • sleeps: 26
  • Location: Montespertoli (Countryside)
  • weekly price: from € 485 to € 1005

Stone villa from the 13th century offers apartments for your vacation in the Chianti hills near Florence. Managed directly by the owners, guests receive personal attention and service while enjoying the self-catering accommodation and the villa's pool.

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Residence Santa Maria

Holiday Apartments Santa Maria near Montaione

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  • apartments: 10
  • sleeps: 23
  • Location: Montaione (Countryside)
  • daily price: from € 50 to € 100
  • weekly price: from € 410 to € 1300

Warm & inviting holiday apartments at Residence Santa Maria between Florence & Pisa are sure to make the perfect vacation in central Tuscany. A colorful green garden in a family run self catering vacation rental only walking distance of local restaurants

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Agriturismo Incrociata

Beautiful Tuscan Farmhouse with Pool near Arezzo

  • apartments: 8
  • sleeps: 28
  • Location: Bucine (Countryside)
  • weekly price: from € 375 to € 1600

Nestled in the Tuscan countryside not far from Arezzo, the farmhouse offers comfortable apartments and two independent holiday homes. The estate has a nice pool and a large park in which guests can really relax.

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Podere Casanova

Holiday Apartments with Pool in Montespertoli

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  • apartments: 5
  • sleeps: 19
  • Location: Montespertoli (Countryside)
  • daily price: from € 56 to € 117
  • weekly price: from € 390 to € 1710

The family friendly wine producing estate Podere Casanova in Chianti provides fully furnished apartments for 2-9 persons. Travel Tuscany, enjoy the large garden & swimming pool, family activities & pizza parties. Reserve with the owner for best prices

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Il Defizio

B&B and vacation apartments in Gambassi Terme

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  • apartments: 7
  • rooms: 6
  • sleeps: 30
  • Location: Gambassi Terme (Countryside)
  • daily price: from € 120 to € 160
  • weekly price: from € 710 to € 1370

Il Defizio offers a genuine Tuscan experience with B&B rooms, self catering apartments and independent vacation rentals. Located in central Tuscany there are many comforts: a panoramic terrace, air conditioned rooms and on site restaurant for guests.

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Podere Villa Bassa

Holiday Home Rental Overlooking the Stupendous Chianti Countrysid

  • apartments: 2
  • sleeps: 18
  • Location: Montespertoli (Countryside)
  • weekly price: from € 1190 to € 2270

The two extra large vacation rental apartments at Podere Villabassa near Montespertoli, feature fantastic gardens, terraces, pool & hot tub. The holiday accommodations can be combined into one large villa with communicating doors for groups of 18 PAX

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Borgo Sicelle

Panoramic Chianti Family Vacation Rental Apartments

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  • apartments: 10
  • sleeps: 33
  • Location: Castellina in Chianti (Countryside)
  • daily price: from € 70 to € 195

10 self catering vacation rental apartments for families with children, couples & groups in Castellina in Chianti. Positioned on a panoramic hillside it offers picture perfect vistas of Chianti and Tuscany, only a short distance from Siena & Florence.

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Il Corbezzolo

Private Romantic Holiday Villa Rental near San Gimignano

  • sleeps: 4
  • Location: Gambassi Terme (Countryside)
  • weekly price: from € 750 to € 980

A one bedroom private villa rental for vacation near San Gimignano and Chianti, promises tranquility, comfort & romantic Tuscan landscapes for your holiday. Perfect base also for a honeymoon.

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Villa Stolli

Luxury Independent Vacation Villa Rental near Florence

  • rooms: 4
  • sleeps: 10
  • Location: Figline Valdarno (Countryside)
  • weekly price: from € 1400 to € 3200

Spacious & luminous Villa for 10 persons with a private panoramic pool and luxury decor, is in a prime position between Florence & Chianti. Easy access to Siena, Pisa and relaxing spa services.

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La Casa in Chianti

In Chianti, overlooking olive groves & vineyards

  • apartments: 2
  • sleeps: 12
  • Location: Gaiole in Chianti (Countryside)
  • daily price: from € 35 to € 45

This beautiful farmhouse near Gaiole in Chianti features 3 holiday rental solutions for families & friends exploring Tuscany. Great views, a Tuscan atmosphere, attentive service & homey comforts for a tranquil vacation.

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Sant' Andrea a Cellole

In the Hills of Chianti, with stunning panoramic views

  • apartments: 3
  • sleeps: 10
  • Location: Montespertoli (Countryside)
  • daily price: from € 90 to € 150
  • weekly price: from € 720 to € 980

These three independent vacation apartments, located between Florence, Siena & San Gimignano promise a tranquil environment with breathtaking views. A spectacular garden, pool & exceptional hospitality by the owners.

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Montrogoli Holiday Home

Simple, elegant and luminous holiday home in Tuscany for 12 PAX

  • rooms: 6
  • sleeps: 12
  • Location: San Casciano in Val di Pesa (Countryside)
  • weekly price: from € 670 to € 4000

Combine the exhilarating experience of Tuscan art, food & wine with the breath taking views of Chianti at this beautifully restored holiday villa for up to 12 persons in luminous spacious accommodations.

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Agriturismo I Poggi

Typical rural farmhouse with pool near Florence

  • rooms: 7
  • Location: Impruneta (Countryside)
  • daily price: from € 80 to € 300

This typical Tuscan farmhouse situated in Impruneta, on the Florentine hills, offers elegant apartments, all provided with modern comforts, free wi-fi and rustic furnishings. Perfect location for biking (free bike rental) and hiking all around.

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tuscany



Home Sweet Home

Vacation Homes and apartments in Chianti are surrounded by a unique and unforgettable landscape, made of sunny hills, vineyards, olive groves, winding country roads, suggestive isolated rural homes and much more.

Vacation homes are often part of agriturismo or villas, and are completely equipped to make your stay very comfortable.

Having their own kitchen and outdoors spaces, these lodgins are particularly suitable for families with children and for all wishing to enjoy a totally relaxing and peaceful vacation, far from the chaos and worries of everyday life.

Car rentals all over Tuscany and Florence

Florence & Tuscany tours

Florence Lucca Pisa Siena Arezzo Grosseto Livorno Pistoia Montecatini Terme San Gimignano Cortona Montepulciano Volterra Casentino Chianti Garfagnana Lunigiana Maremma Mugello Val d'Orcia Versilia Elba Island Etruscan Coast Crete Senesi Argentario