Chianti Vacation Rentals

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Popular Accommodations in Chianti

Apartment for 2 people in Europe, with garden, child-friendly
Arezzo Province
from
$70per night
Vacation house for 4 people in Chiusi, with pool and garden
4.7
5 reviews
Chiusi, Siena Province
from
$78per night
Apartment for 4 people in Siena, with garden
4.7
17 reviews
Siena, Siena Province
from
$54per night
Apartment for 2 people in Lamporecchio, with pool
4.2
23 reviews
Lamporecchio, Pistoia Province
from
$32per night
Apartment for 4 people in San Casciano in Val di Pesa, with garden
3.9
29 reviews
San Casciano in Val di Pesa, Florence Province
from
$47per night
Apartment for 2 people in San Gimignano, with pets
4.8
12 reviews
San Gimignano, Siena Province
from
$84per night
Manor for 4 people in Pienza, with terrace and pool, with pets
4.3
26 reviews
Pienza, Siena Province
from
$61per night
Vacation house for 4 people in Gambassi Terme, with pool
4.5
13 reviews
Gambassi Terme, Florence Province
from
$56per night
Villa for 4 people in Europe, with view and garden as well as pool, with pets
4.6
76 reviews
Arezzo Province
from
$67per night
Apartment for 2 people in Vinci, with pool and balcony
4.4
35 reviews
Vinci, Florence Province
from
$39per night
Vacation house for 4 people in Montevarchi, with terrace
4 pers., 1 bedrooms
3.8
1 review
Montevarchi, Arezzo Province
from
$46per night
Large vacation apartment for 4 people in Florence, with pets
4 pers., 2 bedrooms
4.8
3 reviews
Florence, Florence Province
from
$42per night
Apartment for 4 people in Florence
4 pers., 1 bedrooms
4.8
10 reviews
Florence, Florence Province
from
$79per night
Large vacation apartment for 4 people in Europe
5.0
1 review
Siena Province
from
$56per night
Manor for 4 people in Castellina in Chianti, with pool and terrace
4.5
46 reviews
Castellina in Chianti, Siena Province
from
$61per night
Manor for 3 people in Europe, with pool and terrace, with pets
4.0
533 reviews
Arezzo Province
from
$40per night
Apartment for 4 people in San Casciano in Val di Pesa, with view and pool as well as garden, with pets
4.7
31 reviews
San Casciano in Val di Pesa, Florence Province
from
$71per night
Apartment for 4 people in Montaione, with pool and garden
3.7
5 reviews
Montaione, Florence Province
from
$45per night
Show all

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 5,780
Internet 9,843
Pet allowed 4,257
Balcony/Terrace 4,803
TV 9,119
Air conditioning 5,199
Garden 5,421
Parking 7,726
Washing machine 8,296

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