Chianti Vacation Rentals

Start comparing over 42,967 rentals in Chianti and book at the best price!

Search millions of vacation rentals
+
Compare over 600 websites
=
Find your perfect vacation rental at the best price

Popular Accommodations in Chianti

Apartment for 5 people, with pool
5 pers., 2 bedrooms, 700ft²
4.4
5 reviews
Bucine, Arezzo Province
from
$66per night
Vacation house for 10 people, with garden and pool, with pets
10 pers., 5 bedrooms, 2,153ft²
Gaiole in Chianti, Siena Province
from
$162per night
Apartment for 4 people, with view and pool as well as terrace, with pets
4 pers., 1 bedroom, 538ft²
4.3
37 reviews
Montaione, Florence Province
from
$55per night
Apartment for 3 people, with balcony and pool as well as view
3 pers., 1 bedroom, 431ft²
4.0
40 reviews
Pulicciano, Arezzo Province
from
$41per night
Show all

Vacation Rentals in Chianti

Apartment for 3 people, with balcony and pool as well as view
3 pers., 1 bedroom, 431ft²
4.0
40 reviews
Pulicciano, Arezzo Province
from
$41per night
Apartment for 2 people, with pool and garden
2 pers., 1 bedroom, 398ft²
3.9
4 reviews
Sovicille, Siena Province
from
$53per night
Apartment for 4 people, with terrace
4 pers., 1 bedroom, 484ft²
3.2
23 reviews
Gaiole in Chianti, Siena Province
from
$55per night
Apartment for 2 people, with pool and garden
2 pers., 1 bedroom, 538ft²
4.4
6 reviews
Florence Province
from
$36per night
Vacation apartment for 2 people, with view, with pets
2 pers., 1 bedroom, 377ft²
3.6
1 review
Lamporecchio, Pistoia Province
from
$39per night
Vacation house for 6 people, with jacuzzi and garden as well as sauna, child-friendly
6 pers., 1 bedroom, 861ft²
Certaldo, Florence Province
from
$176per night
Show all

Vacation Rentals where Pets Allowed

Apartment for 3 people, with garden
3 pers., 1 bedroom, 538ft²,
4.9
19 reviews
Siena Province
from
$65per night
Apartment for 4 people, with terrace and pool, with pets
4 pers., 2 bedrooms, 603ft²,
3.9
41 reviews
Florence Province
from
$51per night
Vacation apartment for 3 people, with garden and pool as well as view, with pets
3 pers., 1 bedroom, 646ft²,
3.6
4 reviews
Montaione, Florence Province
from
$82per night
Show all

Vacation Rentals with Pool

Apartment for 3 people, with garden and pool
3 pers., 1 bedroom, 355ft²
3.8
62 reviews
Podere di Poggetto, Florence Province
from
$49per night
Vacation house for 4 people, with pool and garden
4 pers., 1 bedroom, 538ft²
3.0
2 reviews
Gambassi Terme, Florence Province
from
$68per night
Vacation apartment for 4 people, with garden
4 pers., 1 bedroom, 646ft²
4.3
7 reviews
Siena Province
from
$54per night
Show all

Vacation Rentals with Internet

Apartment for 2 people, child-friendly
2 pers., 1 bedroom, 269ft²
4.6
20 reviews
San Gimignano, Siena Province
from
$76per night
Apartment for 5 people, with balcony
5 pers., 2 bedrooms, 1,292ft²
3.1
2 reviews
Florence, Chianti
from
$99per night
Vacation house for 4 people, with sauna and garden
4 pers., 1 bedroom, 538ft²
4.8
4 reviews
Montelupo Fiorentino, Florence Province
from
$55per 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 5,821
Internet 9,359
Pet allowed 3,454
Balcony/Terrace 4,574
TV 8,462
Air conditioning 5,271
Garden 5,395
Parking 6,999
Washing machine 7,816

Prices and availability

Prices

September
October
November
December
January
$259
Aug 01 - Aug 08
$192 per night
Aug 08 - Aug 15
$187 per night
Aug 15 - Aug 22
$185 per night
Aug 22 - Aug 29
$185 per night
Aug 29 - Sep 05
$182 per night
Sep 05 - Sep 12
$174 per night
Sep 12 - Sep 19
$168 per night
Sep 19 - Sep 26
$164 per night
Sep 26 - Oct 03
$156 per night
Oct 03 - Oct 10
$158 per night
Oct 10 - Oct 17
$168 per night
Oct 17 - Oct 24
$161 per night
Oct 24 - Oct 31
$155 per night
Oct 31 - Nov 07
$172 per night
Nov 07 - Nov 14
$160 per night
Nov 14 - Nov 21
$133 per night
Nov 21 - Nov 28
$155 per night
Nov 28 - Dec 05
$220 per night
Dec 05 - Dec 12
$218 per night
Dec 12 - Dec 19
$193 per night
Dec 19 - Dec 26
$210 per night
Dec 26 - Jan 02
$237 per night
Jan 02 - Jan 09
$259 per night
Jan 09 - Jan 16
$223 per night
Average price per week

Availabilities

September
October
November
December
January
67 %
Aug 01 - Aug 08
38 %
Aug 08 - Aug 15
35 %
Aug 15 - Aug 22
37 %
Aug 22 - Aug 29
48 %
Aug 29 - Sep 05
56 %
Sep 05 - Sep 12
61 %
Sep 12 - Sep 19
61 %
Sep 19 - Sep 26
62 %
Sep 26 - Oct 03
63 %
Oct 03 - Oct 10
65 %
Oct 10 - Oct 17
66 %
Oct 17 - Oct 24
67 %
Oct 24 - Oct 31
67 %
Oct 31 - Nov 07
62 %
Nov 07 - Nov 14
61 %
Nov 14 - Nov 21
61 %
Nov 21 - Nov 28
61 %
Nov 28 - Dec 05
60 %
Dec 05 - Dec 12
61 %
Dec 12 - Dec 19
60 %
Dec 19 - Dec 26
59 %
Dec 26 - Jan 02
56 %
Jan 02 - Jan 09
56 %
Jan 09 - Jan 16
57 %
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
  1. Vacation rentals
  2. Italy
  3. Central Italy
  4. Tuscany
  5. Chianti