Vacation Rentals in Chianti

Vacation Rentals in Chianti

Start comparing over 11746 rentals in Chianti and book at the best price!

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Vacation house
Vacation apartment
Pool
Internet
Pets allowed
4.0
 & higher
Free cancellation

Vacation Rentals in Chianti

Vacation rental for 4 people, with yard, with pets in Chianti
Vacation rental for 4 people, with yard, with pets
2 bedrooms
4.8
(17 reviews)
from $66 / night
Vacation rental for 7 people, with yard and view in Chianti
Vacation rental for 7 people, with yard and view
2 bedrooms
4.9
(3 reviews)
from $68 / night
Vacation rental for 4 people, with yard, with pets in Chianti
Vacation rental for 4 people, with yard, with pets
2 bedrooms
4.8
(60 reviews)
from $56 / night
Vacation rental for 16 people, with yard and view in Chianti
Vacation rental for 16 people, with yard and view
10 bedrooms
4.7
(18 reviews)
from $360 / night

Popular Vacation Rentals in Chianti

Vacation rental for 25 people, with pool and view, with pets in Chianti
Vacation rental for 25 people, with pool and view, with pets
12 bedrooms
5.0
from $354 / night
Vacation apartment for 2 people, with terrace in Chianti
Vacation apartment for 2 people, with terrace
1 bedroom
4.3
(5 reviews)
from $32 / night
Vacation rental for 3 people, with view and yard, with pets in Chianti
Vacation rental for 3 people, with view and yard, with pets
2 bedrooms
4.6
(39 reviews)
from $58 / night
Vacation rental for 4 people, with yard in Chianti
Vacation rental for 4 people, with yard
2 bedrooms
4.8
(61 reviews)
from $61 / night

Vacation rentals with free cancellation

Vacation rental for 4 people, with yard and sauna in Chianti
Vacation rental for 4 people, with yard and sauna
2 bedrooms
4.7
(7 reviews)
from $85 / nightFREE cancellation
Vacation rental for 4 people, with yard and pool, with pets in Chianti
Vacation rental for 4 people, with yard and pool, with pets
2 bedrooms
4.0
(40 reviews)
from $74 / nightFREE cancellation
Vacation rental for 2 people, with yard and hot tub as well as sauna in Chianti
Vacation rental for 2 people, with yard and hot tub as well as sauna
1 bedroom
5.0
(3 reviews)
from $114 / nightFREE cancellation
Vacation rental for 2 people, with yard in Chianti
Vacation rental for 2 people, with yard
1 bedroom
4.4
(13 reviews)
from $51 / nightFREE cancellation

Pet-friendly Vacation Rentals

Vacation rental for 4 people, with yard in Chianti
Pet allowed
Vacation rental for 4 people, with yard
2 bedrooms
3.7
(7 reviews)
from $50 / night
Vacation rental for 8 people, with pool and view in Chianti
Pet allowed
Vacation rental for 8 people, with pool and view
4 bedrooms
4.5
(2 reviews)
from $98 / night
Vacation rental for 4 people, with yard and view in Chianti
Pet allowed
Vacation rental for 4 people, with yard and view
1 bedroom
3.9
(33 reviews)
from $56 / night
Vacation rental for 7 people, with terrace and pool, with pets in Chianti
Pet allowed
Vacation rental for 7 people, with terrace and pool, with pets
4 bedrooms
from $143 / night

Vacation Rentals with Pool

Vacation rental for 10 people, with yard and view in Chianti
Pool
Vacation rental for 10 people, with yard and view
4 bedrooms
4.6
(21 reviews)
from $148 / night
Vacation rental for 4 people, with view and yard in Chianti
Pool
Vacation rental for 4 people, with view and yard
2 bedrooms
4.3
(4 reviews)
from $59 / night
Vacation rental for 5 people, with view and terrace, kid friendly in Chianti
Pool
Vacation rental for 5 people, with view and terrace, kid friendly
2 bedrooms
4.6
(3 reviews)
from $66 / night
Vacation rental for 5 people, with yard and view, with pets in Chianti
Pool
Vacation rental for 5 people, with yard and view, with pets
2 bedrooms
5.0
(14 reviews)
from $89 / night

Vacation Rentals with Internet

Vacation apartment for 4 people in Chianti
Internet
Vacation apartment for 4 people
1 bedroom
3.9
(8 reviews)
from $60 / night
Vacation rental for 4 people, with yard and view in Chianti
Internet
Vacation rental for 4 people, with yard and view
1 bedroom
4.6
(30 reviews)
from $73 / night
Vacation rental for 2 people, with yard, with pets in Chianti
Internet
Vacation rental for 2 people, with yard, with pets
1 bedroom
4.6
(9 reviews)
from $48 / night
Vacation rental for 4 people in Chianti
Internet
Vacation rental for 4 people
2 bedrooms
4.1
(4 reviews)
from $102 / nightFREE cancellation

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.
more...
Foiano Della Chiana, Arezzo Province
Vacation Rental • 646 ft² • 2 Bedrooms
5.0
(14 reviews)
3-room house 60 m2. Renovated, simple and beautiful furnishings: living/dining room with satellite TV and tiled stove. 1 double bedroom. 1 double bedroom. Gallery, - 100 cm with 1 bed. Kitchenette (4 hot plates, oven, dishwasher, freezer, pizza oven) with dining table. Exit to the garden, pergola. Shower/bidet/WC. Wood heating. Patio, garden. Terrace furniture, sitting area. View of the countryside. Facilities: washing machine, mosquito net, hair dryer. Internet (WiFi, free). 1 pet/ dog allowed.
from $89 / night
more...
Laterina, Chianti
Vacation Rental • 753 ft² • 1 Bedroom
4.0
(11 reviews)
2-room house 70 m2 on 2 levels, on the ground floor. Beautiful and tasteful furnishings: kitchen-/living room (4 hot plates, dishwasher, microwave, electric coffee machine) with dining table and CD-player. Exit to the garden, to the patio, to the swimming pool. Shower/bidet/WC. Gas heating (extra). Heating available only from 01.11. to 15.04. Upper floor: 1 open double bedroom. Open living/sleeping room with 2 sofabeds and TV. Terrace. Terrace furniture, barbecue, box-room. Facilities: hair dryer. Internet (WiFi). 1 pet/ dog allowed. The double bedroom and the living roomwith the 2 armchair...
from $76 / night
more...
Lilliano, Chianti
Vacation Rental • 1615 ft² • 4 Bedrooms
Detached holiday farmhouse made of stone in the heart of Chianti Classico, 5km from Castellina in Chianti. The house is located inside a renowned Tuscan estate, which produces extra virgin olive oil and an excellent wine. The accommodation is quietly located and offers beautiful views over the vineyards and hills. At guests’ disposal: well-kept garden with private swimming pool (open from 9 am to 8 pm), barbecue area with stone BBQ and bathroom. Baby bed, high chair and extra linen change available on request (locally to be paid for). Access via 500 m gravel road. Some suggestions for your ...
from $143 / night

Most popular in Chianti

Pool 6,088
Internet 6,945
Pets allowed 3,584
Balcony/Terrace 3,054
TV 6,217
Air conditioning 4,000

Prices and availability

Vacation rental prices Chianti

$201for 8 Oct - 15 Oct
$226 annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Average price per week

Vacation rentals availability Chianti

39%for 8 Oct - 15 Oct
53% annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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.

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

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