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Vacation Rentals in Chianti

Vacation Rentals in Chianti

Start comparing over 6,981 rentals in Chianti and book at the best price!

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BarnsVacation housesPoolPets allowed
8.0
 & higher
9.0
 & higher
Free cancellation

Child-friendly vacation rentals

Cavriglia, Chianti

9.9

Vacation rental for 6 people, with balcony and yard

from $157 per night

Castellina in Chianti, Chianti

9.1

Vacation rental for 9 people, with yard and view as well as terrace, with pets

Free cancellation

from $161 per night

Montevarchi, Chianti

9.4

Vacation rental for 10 people, with yard and view as well as terrace

Free cancellation

from $312 per night

Montevarchi, Chianti

9.3

Vacation rental for 22 people, with yard and view as well as balcony, with pets

Free cancellation

from $559 per night
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Vacation rentals with pets allowed

Castelfranco Piandiscò (municipality), Valdarno

9.7

Vacation rental for 4 people, with lake view and yard as well as view

Free cancellation

from $104 per night
Star Host
Star hosts are experienced and highly rated hosts with a commitment to provide reliably great stays.

Radda in Chianti, Chianti

9.5

Vacation rental for 6 people, with yard

Free cancellation

from $186 per night
Star Host
Star hosts are experienced and highly rated hosts with a commitment to provide reliably great stays.

Gaiole in Chianti, Chianti

9.2

Vacation rental for 4 people, with yard, with pets

Free cancellation

from $90 per night

Radda in Chianti, Chianti

9.6

Vacation rental for 14 people, with balcony and yard

Free cancellation

from $431 per night
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Vacation rentals in Chianti

Pontassieve, Chianti

8.9

Vacation rental for 7 people, with yard and pool

from $110 per night
Star Host
Star hosts are experienced and highly rated hosts with a commitment to provide reliably great stays.

Castelnuovo Berardenga (Comune), Chianti

9.6

Vacation rental for 4 people, with yard

Free cancellation

from $155 per night

Castelfranco Piandiscò (municipality), Valdarno

9.4

Vacation rental for 6 people, with terrace and yard

Free cancellation

from $118 per night

Castiglion Fibocchi, Valdarno

10.0

Vacation rental for 20 people, with pool and yard, with pets

from $433 per night
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Vacation rentals with a lake view

Star Host
Star hosts are experienced and highly rated hosts with a commitment to provide reliably great stays.

Radda in Chianti, Chianti

9.5

Vacation rental for 5 people, with lake view and yard

Free cancellation

from $230 per night

Pelago, Chianti

10.0

Vacation rental for 8 people, with lake view and yard

from $281 per night

Castelfranco Piandiscò (municipality), Valdarno

10.0

Vacation rental for 3 people, with yard and view as well as lake view

Free cancellation

from $81 per night

Certaldo, Chianti

8.2

Vacation rental for 8 people, with yard and lake view

from $244 per night
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Vacation rentals with free cancellation

Chianti

8.6

Vacation apartment for 4 people

Free cancellation

from $90 per night
Star Host
Star hosts are experienced and highly rated hosts with a commitment to provide reliably great stays.

Gaiole in Chianti, Chianti

9.2

Vacation rental for 4 people, with pets

Free cancellation

from $116 per night

Montaione, Chianti

9.4

Vacation rental for 26 people, with yard

Free cancellation

from $687 per night

Bucine region, Chianti

8.7

Vacation rental for 5 people, with terrace and yard, kid friendly

Free cancellation

from $140 per night
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Current vacation rental deals in Chianti

Sovicille, Chianti

9.9

Vacation rental for 6 people, with hot tub and yard as well as sauna

Free cancellation

Wed, 09/30 - Thu, 10/08

$1,844 · 8 nights

Casole d'Elsa, Chianti

9.7

Vacation rental for 4 people, with yard, with pets

Free cancellation

Wed, 09/30 - Thu, 10/08

$1,849 · 8 nights

Castelnuovo Berardenga (Comune), Chianti

7.7

Vacation rental for 4 people, with yard

Free cancellation

Wed, 09/30 - Thu, 10/08

$1,673 · 8 nights

Castelnuovo Berardenga (Comune), Chianti

9.5

Vacation rental for 4 people, with yard

Free cancellation

Wed, 09/30 - Thu, 10/08

$1,569 · 8 nights

Find Vacation Rentals in Chianti

Map

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

Best Vacation Rentals in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 7 Guests in Reggello, Valdarno
Vacation Rental for 7 Guests in Reggello, Valdarno, Picture 1
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more...
Reggello, Valdarno
Vacation Rental • 1130 ft² • 3 Bedrooms
9.2
(23 reviews)
"La Torre", 4-room semi-detached house 105 m2 on 3 levels, on the ground floor. Rustic and cosy furnishings: living/dining room with 1 sofabed, dining table and satellite TV. Open kitchen (4 hot plates, oven, dishwasher, freezer). Exit to the garden. Shower/bidet/WC. Upper floor: 1 double bedroom. Bath/bidet/WC. 2nd upper floor: 1 room with 2 beds. 1 double bedroom with separate WC. Gas heating. Terrace furniture. Very beautiful view of the countryside. Parking. Please note: non-smokers only. Outdoor space equipped with about 30 square meters. IT048035C24PTY8VL7
from $158 / night
Vacation Rental for 4 Guests in Loro Ciuffenna, Valdarno
Vacation Rental for 4 Guests in Loro Ciuffenna, Valdarno, Picture 1
Vacation Rental for 4 Guests in Loro Ciuffenna, Valdarno, Picture 2
Vacation Rental for 4 Guests in Loro Ciuffenna, Valdarno, Picture 3
Vacation Rental for 4 Guests in Loro Ciuffenna, Valdarno, Picture 4
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Loro Ciuffenna, Valdarno
Vacation Rental • 377 ft² • 1 Bedroom
8.7
(14 reviews)
This stylish 1-bedroom farmhouse in Loro Ciuffenna hosts 4 guests and is ideal for a family or group to stay. There is a shared swimming pool for a refreshing dip and a garden to relax. You can try the local cuisine from the restaurants, only 2 km away. The town center with nightlife pubs and supermarket are 3 km from the stay. The farmhouse has central heating and fireplace for a comfortable stay. Relish a sizzling platter of barbecue from the furnished garden. You can bring 2 pets at an additional cost of €10/pet/stay. Kids have a high chair and a children’s bed to use. The farmhouse also...
from $92 / night
Vacation Rental for 6 Guests in Chianti
Vacation Rental for 6 Guests in Chianti, Picture 1
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Vacation Rental for 6 Guests in Chianti, Picture 4
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Chianti
Vacation Rental • 700 ft² • 3 Bedrooms
8.8
(35 reviews)
"Torsoli", 4-room semi-detached house 65 m2, on the upper ground floor. Tasteful furnishings: living/dining room with open-hearth fireplace and satellite TV. 1 room with 2 beds. 1 double bedroom. Open gallery, ceiling height 100 - 190 cm with 2 beds. Kitchenette (4 hot plates, oven, dishwasher, kettle, freezer). 2 showers/bidet/WC. Heating. Small garden. Terrace furniture. Facilities: Internet (WiFi). Maximum 1 pet/ dog allowed. IT048021C2KGT7DHNB
from $188 / night

Popular Destinations in Chianti

    Prices and availability

    Current Vacation rental prices Chianti

    $261for 6 Dec - 13 Dec
    $314 annual average
    Dec
    Jan
    Feb
    Mar
    Apr
    May
    Jun
    Jul
    Aug
    Sep
    Oct
    Nov
    Dec
    Average price per week

    Current vacation rental availability Chianti

    38%for 6 Dec - 13 Dec
    56% annual average
    Dec
    Jan
    Feb
    Mar
    Apr
    May
    Jun
    Jul
    Aug
    Sep
    Oct
    Nov
    Dec
    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

    FAQs: Vacation Rentals in Chianti

    How much do you pay, on average, for vacation rentals in Chianti?

    Our data shows that Chianti had an average price of $234 per night, a relatively high one for a destination in Italy.

    During which months are vacation rentals cheaper in Chianti?

    According to the previous year, the months that are the cheapest in Chianti are November, April and May, with average prices of $215, $221, and $221, respectively.

    During which months are vacation rentals more expensive in Chianti?

    Last year, the month that had the highest annual average in Chianti was January, with an average price of $258 per night. This was followed by July, with an average of $257, and then August, with $253.

    Are there usually many vacation rentals available in Chianti?

    When planning a vacation to Chianti, we recommend you to be proactive as 54% of rentals are usually booked, according to last year's data.

    When are more vacation rentals available?

    The best months to find free accommodation in Chianti are April (the average amount of properties that are free reached 64% of the total last year), May (63%), and June (57%).

    When are there fewer vacation rental options available in Chianti?

    The months with the lowest properties available in Chianti are, in order, August, July, and December with respective average availability figures of 20%, 37%, and 38%, based on the previous year.

    How many vacation rentals does Holidu have in Chianti?

    Holidu has around 17,000 vacation rentals in Chianti, provided by 92 different partners.

    Most popular in Chianti

    Pool
    (2,380)
    Internet
    (2,804)
    Pets allowed
    (1,642)
    Balcony/Terrace
    (1,721)
    TV
    (2,295)
    Air conditioning
    (1,367)
    Yard
    (2,342)
    Parking
    (2,409)
    Washing machine
    (2,319)

    Vacation destinations in Chianti

    Vacation destinations nearby

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