Chianti Vacation Rentals

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Popular Accommodations in Chianti

Large vacation apartment for 6 people in Gambassi Terme, with pets
4.4
1 review
Gambassi Terme, Florence Province
from
$44per night
Vacation apartment for 2 people in Arezzo, child-friendly
Arezzo, Arezzo Province
from
$52per night
Apartment for 2 people in Lamporecchio, with pool
4.4
20 reviews
Lamporecchio, Pistoia Province
from
$33per night
Apartment for 4 people in Montaione, with garden and pool as well as view, with pets
4.3
37 reviews
Montaione, Florence Province
from
$57per night
Country house for 4 people in Monsummano Terme, with garden, with pets
4.6
6 reviews
Monsummano Terme, Pistoia Province
from
$100per night
Large vacation house for 10 people in Radicondoli, with garden, with pets
10 pers., 4 bedrooms, 1,830ft²
Radicondoli, Siena Province
from
$243per night
Vacation house for 2 people in Europe, with garden
4.9
41 reviews
Siena Province
from
$123per night
Apartment for 4 people in Empoli, with garden
4.3
67 reviews
Empoli, Florence Province
from
$56per night
Homestay for 2 people in Greti, with garden, with pets
4.3
92 reviews
Greti, Florence Province
from
$98per night
Country house for 2 people in Lastra a Signa, with garden
2 pers., 215ft²
4.3
237 reviews
Lastra a Signa, Prato Province
from
$58per night
Vacation house for 3 people in Europe, with garden, with pets
4.4
23 reviews
Siena Province
from
$80per night
Apartment for 5 people in Lamporecchio, with garden
4.5
22 reviews
Lamporecchio, Pistoia Province
from
$168per night
Apartment for 4 people in San Gimignano, with garden and view as well as pool, with pets
4.4
31 reviews
San Gimignano, Siena Province
from
$67per night
Country house for 5 people in Vinci, with jacuzzi and garden
4.4
19 reviews
Vinci, Florence Province
from
$157per night
Villa for 8 people in Pienza, with garden and pool as well as view
Pienza, Val d'Orcia
from
$222per night
Apartment for 3 people in Europe, with garden
5.0
18 reviews
Siena Province
from
$55per night
Country house for 4 people in Serravalle Pistoiese, with jacuzzi and garden
4.9
31 reviews
Serravalle Pistoiese, Pistoia Province
from
$139per night
Apartment for 3 people in Florence, with pool and garden
3 pers., 1 bedrooms, 538ft²
4.8
194 reviews
Florence, Florence Province
from
$151per 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 6,153
Internet 10,440
Pet allowed 4,382
Balcony/Terrace 5,144
TV 9,766
Air conditioning 5,566
Garden 5,788
Parking 8,191
Washing machine 9,042

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