Chianti Vacation Rentals

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Popular Accommodations in Chianti

Vacation house for 6 people
6 pers., 3 bedrooms, 1,076ft²
2.0
2 reviews
San Casciano in Val di Pesa, Florence Province
from
$77per night
Apartment for 3 people, with pool and balcony
3.9
61 reviews
Podere di Poggetto, Florence Province
from
$49per night
Apartment for 4 people, with garden and pool
3.9
6 reviews
Montaione, Florence Province
from
$75per night
Apartment for 2 people, with pool and garden as well as view
4.6
72 reviews
San Gimignano, Siena Province
from
$60per night
Vacation house for 16 people, with pool and garden
16 pers., 6 bedrooms, 4,628ft²
5.0
4 reviews
Sinalunga, Siena Province
from
$351per night
Vacation house for 8 people, with view and pool as well as garden
5.0
1 review
Casole d'Elsa, Siena Province
from
$142per night
Apartment for 3 people, with garden and pool
4.1
54 reviews
Arezzo Province
from
$43per night
Vacation house for 4 people, with view and pool as well as terrace, with pets
3.8
13 reviews
Monticiano, Siena Province
from
$59per night
Apartment for 4 people, with pool
4.2
25 reviews
Lamporecchio, Pistoia Province
from
$41per night
Castle for 2 people, with pool and garden as well as view
4.2
520 reviews
Montespertoli, Florence Province
from
$62per night
Vacation apartment for 4 people, with view and pool, with pets
3.8
13 reviews
Monte San Savino, Arezzo Province
from
$37per night
Vacation house for 8 people, with terrace
3.5
5 reviews
San Casciano in Val di Pesa, Florence Province
from
$120per night
Farmhouse for 6 people, with balcony/terrace and pool
6 pers., 2 bedrooms, 1,938ft²
Monteroni d'Arbia, Siena Province
from
$147per night
Apartment for 2 people, with balcony and pool as well as view
4.2
12 reviews
San Gimignano, Siena Province
from
$91per night
Vacation apartment for 4 people, with view
4 pers., 2 bedrooms, 753ft²
4.7
17 reviews
San Gimignano, Siena Province
from
$53per night
Apartment for 4 people, with terrace and pool, with pets
3.9
41 reviews
Florence Province
from
$48per night
Vacation apartment for 3 people
5.0
3 reviews
San Gimignano, Siena Province
from
$41per night
Apartment for 10 people, with garden and pool as well as jacuzzi, child-friendly
Serravalle Pistoiese, Pistoia Province
from
$238per night
Show all

Highlights 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 6,606
Internet 11,193
Pet allowed 4,068
Balcony/Terrace 5,181
TV 10,030
Air conditioning 6,519
Garden 5,958
Parking 8,025
Washing machine 9,150

Prices and availability

Prices

July
August
September
October
November
$217
Jun 20 - Jun 27
$159 per night
Jun 27 - Jul 04
$169 per night
Jul 04 - Jul 11
$180 per night
Jul 11 - Jul 18
$188 per night
Jul 18 - Jul 25
$196 per night
Jul 25 - Aug 01
$198 per night
Aug 01 - Aug 08
$196 per night
Aug 08 - Aug 15
$195 per night
Aug 15 - Aug 22
$198 per night
Aug 22 - Aug 29
$200 per night
Aug 29 - Sep 05
$188 per night
Sep 05 - Sep 12
$170 per night
Sep 12 - Sep 19
$159 per night
Sep 19 - Sep 26
$149 per night
Sep 26 - Oct 03
$144 per night
Oct 03 - Oct 10
$147 per night
Oct 10 - Oct 17
$145 per night
Oct 17 - Oct 24
$150 per night
Oct 24 - Oct 31
$158 per night
Oct 31 - Nov 07
$202 per night
Nov 07 - Nov 14
$192 per night
Nov 14 - Nov 21
$202 per night
Nov 21 - Nov 28
$217 per night
Nov 28 - Dec 05
$173 per night
Average price per week

Availabilities

July
August
September
October
November
70 %
Jun 20 - Jun 27
62 %
Jun 27 - Jul 04
62 %
Jul 04 - Jul 11
63 %
Jul 11 - Jul 18
62 %
Jul 18 - Jul 25
60 %
Jul 25 - Aug 01
57 %
Aug 01 - Aug 08
55 %
Aug 08 - Aug 15
53 %
Aug 15 - Aug 22
54 %
Aug 22 - Aug 29
60 %
Aug 29 - Sep 05
63 %
Sep 05 - Sep 12
64 %
Sep 12 - Sep 19
64 %
Sep 19 - Sep 26
64 %
Sep 26 - Oct 03
65 %
Oct 03 - Oct 10
67 %
Oct 10 - Oct 17
68 %
Oct 17 - Oct 24
69 %
Oct 24 - Oct 31
70 %
Oct 31 - Nov 07
65 %
Nov 07 - Nov 14
64 %
Nov 14 - Nov 21
64 %
Nov 21 - Nov 28
64 %
Nov 28 - Dec 05
63 %
Percentage of available rentals

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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