Vacation Rentals in Chianti

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Best vacation rental deals in Chianti

Fri, 06/04 - Fri, 06/11
Apartment for 2 people, with garden, child-friendly
2 pers., 1 bedroom
4.6
35 reviews

7 nights
$535

$664-19%
Fri, 06/04 - Fri, 06/11
Vacation house for 2 people, with terrace, with pets
2 pers., 1 bedroom, 484ft²
4.4
29 reviews

7 nights
$703

$758-7%
Fri, 06/04 - Fri, 06/11
Vacation house for 2 people, with pool and garden, child-friendly
2 pers., 1 bedroom
4.4
42 reviews

7 nights
$714

$758-6%

Vacation Rentals in Chianti

Vacation house for 4 people, with pool and garden, with pets
4 pers., 2 bedrooms, 592ft²
4.6
57 reviews
Arezzo Province

from
$47
per night

Vacation house for 5 people, with view and garden, with pets
5 pers., 2 bedrooms, 1,292ft²
4.2
10 reviews
Arezzo, Arezzo Province

from
$88
per night

Apartment for 2 people, with pool and terrace
2 pers., 1 bedroom, 377ft²
3.6
17 reviews
Lamporecchio, Pistoia Province

from
$31
per night

Apartment for 2 people, with garden and pool as well as view
2 pers., 1 bedroom, 560ft²
4.6
70 reviews
San Gimignano, Siena Province

from
$56
per night

Apartment for 3 people, with view and pool as well as garden, with pets
3 pers., 1 bedroom, 431ft²
4.6
2 reviews
Lamporecchio, Pistoia Province

from
$64
per night

Apartment for 8 people, with garden and pool, with pets
8 pers., 3 bedrooms, 883ft²
5.0
1 review
Montaione, Florence Province

from
$159
per night

Apartment for 2 people, with view and pool as well as garden
2 pers., 1 bedroom, 301ft²
4.0
43 reviews
Pulicciano, Arezzo Province

from
$35
per night

Vacation house for 14 people
14 pers., 6 bedrooms, 2,153ft²
4.3
9 reviews
Gambassi Terme, Florence Province

from
$114
per night

Vacation house for 2 people, with garden and pool, with pets
2 pers., 1 bedroom, 344ft²
4.1
45 reviews
San Miniato, Pisa Province

from
$50
per night

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Pet-friendly Vacation Rentals

Apartment for 3 people, with garden
3 pers., 1 bedroom, 538ft², Pets allowed
4.9
15 reviews
Siena Province

from
$69
per night

Apartment for 4 people, with terrace and pool
4 pers., 2 bedrooms, 538ft², Pets allowed
3.8
22 reviews
Siena Province

from
$64
per night

Vacation house for 6 people, with garden and view as well as pool, with pets
6 pers., 3 bedrooms, 1,507ft², Pets allowed
4.6
7 reviews
Arezzo Province

from
$119
per night

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Vacation Rentals with Pool

Vacation apartment for 4 people, with terrace and view
4 pers., 2 bedrooms, 592ft²
4.7
3 reviews
Loro Ciuffenna, Arezzo Province

from
$45
per night

Vacation house for 6 people, with pool and garden
6 pers., 3 bedrooms, 1,292ft²
4.7
8 reviews
Arezzo Province

from
$113
per night

Apartment for 6 people, with children pool and garden as well as pool
6 pers., 2 bedrooms, 592ft²
4.5
9 reviews
Arezzo Province

from
$73
per night

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Vacation Rentals with Internet

Vacation apartment for 4 people
4 pers., 1 bedroom, 538ft²
4.6
3 reviews
San Gimignano, Siena Province

from
$57
per night

Vacation house for 8 people, with pool and garden, with pets
8 pers., 4 bedrooms, 1,206ft²
3.7
3 reviews
Florence Province

from
$103
per night

Castle for 2 people, with view and pool as well as garden, child-friendly
2 pers., 1 bedroom, 269ft²
4.5
200 reviews
Montespertoli, Florence Province

from
$67
per night

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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 5,425
Internet 9,049
Pet allowed 3,596
Balcony/Terrace 4,602
TV 7,790
Air conditioning 5,157
Garden 3,000
Parking 6,913
Washing machine 7,491

Prices and availability

Prices

February
March
April
May
June
July
$268
Jan 23 - Jan 30
$198 per night
Jan 30 - Feb 06
$205 per night
Feb 06 - Feb 13
$207 per night
Feb 13 - Feb 20
$210 per night
Feb 20 - Feb 27
$229 per night
Feb 27 - Mar 06
$235 per night
Mar 06 - Mar 13
$214 per night
Mar 13 - Mar 20
$214 per night
Mar 20 - Mar 27
$222 per night
Mar 27 - Apr 03
$225 per night
Apr 03 - Apr 10
$233 per night
Apr 10 - Apr 17
$234 per night
Apr 17 - Apr 24
$231 per night
Apr 24 - May 01
$232 per night
May 01 - May 08
$233 per night
May 08 - May 15
$232 per night
May 15 - May 22
$234 per night
May 22 - May 29
$238 per night
May 29 - Jun 05
$244 per night
Jun 05 - Jun 12
$243 per night
Jun 12 - Jun 19
$247 per night
Jun 19 - Jun 26
$253 per night
Jun 26 - Jul 03
$258 per night
Jul 03 - Jul 10
$268 per night
Average price per week

Availabilities

February
March
April
May
June
July
71 %
Jan 23 - Jan 30
53 %
Jan 30 - Feb 06
52 %
Feb 06 - Feb 13
54 %
Feb 13 - Feb 20
54 %
Feb 20 - Feb 27
54 %
Feb 27 - Mar 06
54 %
Mar 06 - Mar 13
56 %
Mar 13 - Mar 20
57 %
Mar 20 - Mar 27
59 %
Mar 27 - Apr 03
62 %
Apr 03 - Apr 10
66 %
Apr 10 - Apr 17
69 %
Apr 17 - Apr 24
69 %
Apr 24 - May 01
68 %
May 01 - May 08
70 %
May 08 - May 15
71 %
May 15 - May 22
70 %
May 22 - May 29
67 %
May 29 - Jun 05
66 %
Jun 05 - Jun 12
68 %
Jun 12 - Jun 19
67 %
Jun 19 - Jun 26
68 %
Jun 26 - Jul 03
68 %
Jul 03 - Jul 10
67 %
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

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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