Chianti Vacation Rentals

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Popular Accommodations in Chianti

Apartment for 2 people, with terrace and pool as well as view
4.4
35 reviews
Vinci, Florence Province
from
$32per night
Apartment for 2 people, with pool and terrace as well as view, with pets
4.6
86 reviews
Castellina in Chianti, Siena Province
from
$64per night
Vacation house for 4 people, with pool
4.6
13 reviews
Gambassi Terme, Florence Province
from
$64per night
Vacation house for 5 people, with pool and sauna
5 pers., 1 bedrooms, 646ft²
5.0
5 reviews
Pisa Province
from
$84per night
Apartment for 3 people, with terrace and pool
3.8
58 reviews
Podere di Poggetto, Florence Province
from
$48per night
Apartment for 4 people, with view and terrace as well as pool, with pets
4.4
41 reviews
San Gimignano, Siena Province
from
$51per night
Vacation apartment for 4 people, with terrace
4.0
3 reviews
Monticiano, Siena Province
from
$47per night
Apartment for 2 people, with view and pool as well as garden
4.6
74 reviews
San Gimignano, Siena Province
from
$44per night
Vacation house for 4 people, with terrace and pool, with pets
4.6
58 reviews
Arezzo Province
from
$57per night
Apartment for 4 people, with view and pool as well as garden
4.8
53 reviews
Arezzo Province
from
$62per night
Vacation apartment for 5 people
5.0
1 review
Sovicille, Siena Province
from
$45per night
Vacation house for 5 people, with terrace and view, with pets
4.7
20 reviews
Chiusdino, Siena Province
from
$96per night
Apartment for 6 people, with pool and garden, with pets
4.7
40 reviews
Ulignano (Pisa), Pisa Province
from
$59per night
Apartment for 2 people, with view and pool, with pets
3.9
18 reviews
Colle di Val d'Elsa, Siena Province
from
$32per night
Vacation apartment for 4 people, with view, with pets
4.0
17 reviews
Monte San Savino, Arezzo Province
from
$34per night
Vacation house for 5 people, with garden and pool as well as view, with pets
4.8
21 reviews
Florence Province
from
$72per night
Apartment for 2 people, with view and pool
4.4
66 reviews
Siena Province
from
$77per night
Vacation house for 9 people, with pool and terrace
4.6
21 reviews
Montaione, Florence Province
from
$107per night
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Highlights in Chianti

  • Excursion to the metropolis Florence
  • Cycling tours through the unique landscape
  • Shopping and medieval fortresses in Castellina
  • Radda as a starting point for visiting the wineries

Most popular in Chianti

Pool 5,821
Internet 10,366
Pet allowed 3,793
Balcony/Terrace 5,187
TV 9,733
Air conditioning 5,653
Garden 5,590
Parking 7,935
Washing machine 8,861

Vacation rentals in Chianti

Spend your holidays in the midst of a fantastic landscape of vineyards.

The Chianti region has countless vacation rentals to offer in the midst of a breathtaking hilly landscape. Take a closer look at the apartments in the picturesque towns and cities if you want to enjoy absolute comfort with a doorman and breakfast service. You can also rent a vacation rental in Chianti, which will give you many moments of relaxation in the garden. The stone fincas often have a pool and sometimes a sauna.

Holiday in Chianti

Location and orientation

The range of hills of the same name as a perfect holiday resort to relax in

Chianti is the name of an area in Italy located in the centre of Tuscany. At the same time, Chianti is a chain of hills, the highest point of which is Monte San Michele, 893 metres high. A part of Chianti stretches over the southeastern edge of the city of Florence. Other important places are Castellina, Greve, Montefioralle and Melazzano.

Idyll in Tuscany
Idyll in Tuscany
In Chianti, the famous Chianti wine has been cultivated for centuries and its production area accounts for about one third of Tuscany as a whole.

Top 3 travel tips

1. Explore the unique landscape by bike

The main attraction of Chianti is the landscape itself. This is characterised by fertile gardens, which are also an important habitat for game. The best way to explore the region is on two wheels.

2. Visit the charming town of Castellina

Castellina is a small town where many exclusive restaurants, charming boutiques and underground shops invite you to stroll and linger. You can also visit the fortress of Palazzo Ugolino, the 12th century Castello di Fonterutoli and the 11th century Castello di Rencine not far from Villa di Rencine, which is now a winery.

3. Taste the wine of the region in Radda

A popular centre for wine lovers is Radda. Start your tour in the heart of the city, at the piazza with town hall, fountains and loggias. From here the most famous wineries of the region are very easy to reach. You will find a vineyard in the Castello di Monterinaldi, a castle of Etruscan origin.

Restaurant in Tuscany
Restaurant in Tuscany
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