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 SerelleAdd to
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  • Apartments: 15
  • Sleeps: 68
  • Location: Barberino Val d'Elsa (Countryside)
  • Weekly price:From € 700to €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 QuadrifoglioAdd to
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  • Apartments: 14
  • Rooms: 5
  • Location: Gambassi Terme (Countryside)
  • Daily price:From € 90to €270
  • Weekly price:From € 850to €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 TorriAdd to
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  • Apartments: 9
  • Sleeps: 26
  • Location: Montespertoli (Countryside)
  • Weekly price:From € 485to €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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Agriturismo IncrociataAdd to
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  • Apartments: 8
  • Sleeps: 28
  • Location: Bucine (Countryside)
  • Weekly price:From € 375to €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 CasanovaAdd to
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  • Apartments: 5
  • Sleeps: 19
  • Location: Montespertoli (Countryside)
  • Daily price:From € 56to €117
  • Weekly price:From € 390to €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 DefizioAdd to
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  • Apartments: 7
  • Rooms: 6
  • Sleeps: 30
  • Location: Gambassi Terme (Countryside)
  • Daily price:From € 120to €160
  • Weekly price:From € 710to €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 BassaAdd to
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  • Apartments: 2
  • Sleeps: 18
  • Location: Montespertoli (Countryside)
  • Weekly price:From € 1190to €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 SicelleAdd to
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  • Apartments: 10
  • Sleeps: 33
  • Location: Castellina in Chianti (Countryside)
  • Daily price:From € 70to €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 CorbezzoloAdd to
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  • Sleeps: 4
  • Location: Gambassi Terme (Countryside)
  • Weekly price:From € 750to €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 La MediceaAdd to
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  • Sleeps: 12
  • Location: Impruneta (Countryside)
  • Weekly price:From € 3400to €3800

Historical villa on the edge of Chianti is just 7 km from the center of Florence. The rental villa includes spacious accommodations, modern amenities as well as a beautiful pool with panoramic views over the countryside.

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Villa StolliAdd to
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  • Rooms: 4
  • Sleeps: 10
  • Location: Figline Valdarno (Countryside)
  • Weekly price:From € 1400to €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 ChiantiAdd to
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  • Apartments: 2
  • Sleeps: 12
  • Location: Gaiole in Chianti (Countryside)
  • Daily price:From € 180to €300

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 CelloleAdd to
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  • Apartments: 3
  • Sleeps: 10
  • Location: Montespertoli (Countryside)
  • Daily price:From € 90to €150
  • Weekly price:From € 720to €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 HomeOnline
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  • Rooms: 6
  • Sleeps: 12
  • Location: San Casciano in Val di Pesa (Countryside)
  • Weekly price:From € 670to €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 PoggiOnline
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  • Rooms: 7
  • Location: Impruneta (Countryside)
  • Daily price:From € 80to €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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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.


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