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

Barberino Tavarnelle, Chianti

9.4

Vacation rental for 2 people, with view and yard as well as terrace, with pets

from $70 per night

Chianti

9.1

Vacation rental for 2 people, with pets

from $88 per night

Castelnuovo Berardenga (Comune), Chianti

9.6

Vacation rental for 6 people, with terrace and yard as well as pool, with pets

from $166 per night

Castellina in Chianti, Chianti

9.2

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

from $73 per night

Vacation rentals with pets allowed

Castelfranco Piandiscò (municipality), Valdarno

9.5

Vacation rental for 2 people, with yard, with pets

Free cancellation

from $73 per night

Monte San Savino, Chianti

9.1

Vacation rental for 2 people, with yard, with pets

Free cancellation

from $119 per night

San Quirico d'Orcia, Val d'Orcia

9.1

Vacation apartment for 2 people

from $67 per night

Gaiole in Chianti, Chianti

9.7

Vacation rental for 4 people, with pets

Free cancellation

from $91 per night

Vacation rentals in Chianti

Castelnuovo Berardenga (Comune), Chianti

9.2

Vacation rental for 3 people, with yard and sauna

Free cancellation

from $101 per night

Chianti

8.6

Vacation rental for 2 people, with yard

Free cancellation

from $119 per night

Chianti

8.8

Vacation apartment for 4 people

Free cancellation

from $105 per night

Rignano sull'Arno, Valdarno

8.4

Vacation apartment for 2 people, with pool and yard

Free cancellation

from $86 per night

Vacation rentals with a lake view

Castelfranco Piandiscò (municipality), Valdarno

10.0

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

Free cancellation

from $79 per night

Castelfranco Piandiscò (municipality), Valdarno

10.0

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

Free cancellation

from $102 per night

Radda in Chianti, Chianti

9.6

Vacation rental for 5 people, with lake view and yard

Free cancellation

from $192 per night

Castelfranco Piandiscò (municipality), Valdarno

9.0

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

Free cancellation

from $102 per night

Vacation rentals with free cancellation

Monteriggioni, Chianti

9.0

Vacation rental for 3 people, with yard

Free cancellation

from $113 per night

Castiglion Fibocchi, Valdarno

8.0

Villa for 6 people, with yard

Free cancellation

from $113 per night

Castiglion Fibocchi, Valdarno

9.1

Villa for 4 people, with yard, with pets

Free cancellation

from $102 per night

Pelago, Valdarno

9.9

Vacation rental for 4 people, with yard

Free cancellation

from $113 per night

Current vacation rental deals in Chianti

Castiglione d'Orcia region, Val d'Orcia

9.8

Vacation rental for 6 people, with yard, with pets

Sat, 05/10 - Sat, 05/17

$1,665 · 7 nights

Terranuova Bracciolini, Valdarno

9.4

Vacation rental for 8 people, with yard

Free cancellation

Tue, 08/12 - Wed, 08/20

$5,891 · 8 nights

Gaiole in Chianti, Chianti

9.4

Vacation rental for 4 people, with yard, with pets

Free cancellation

Sat, 08/09 - Sat, 08/23

$2,311 · 14 nights

Barberino Tavarnelle, Chianti

Vacation rental for 12 people, with yard

Free cancellation

Tue, 09/23 - Tue, 09/30

$4,229 · 7 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 2 Guests in Chianti
Vacation Rental for 2 Guests in Chianti, Picture 1
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Chianti
Vacation Rental • 581 ft² • 1 Bedroom
8.2
(23 reviews)
Spend romantic moments in this apartment with shared pool. It is located in a farmhouse in the heart of Chianti Classico, near Greve in Chianti, a few steps from the medieval castle. The apartment is located in the company center, and the pool is 600 meters away. With 1 bedroom, it is the ideal accommodation for a couple. Greve has so much to offer, including shops, restaurants and pizzerias. Its advantageous location in Chianti offers countless options for the most curious vacationers. A must visit are Panzano (8km), Radda (18 km), Gaiole (29 km), Castellina (19 km), Siena (46 km) or the e...
from $64 / night
Vacation Rental for 3 Guests in Bucine region, Chianti
Vacation Rental for 3 Guests in Bucine region, Chianti, Picture 1
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Bucine region, Chianti
Vacation Rental • 538 ft² • 1 Bedroom
8.3
(23 reviews)
This lovely holiday home is situated in Bucine. Ideal for a family, it can accommodate 3 guests and has 1 bedroom. It also has a swimming pool for you to have a refreshing dip on a sunny day.The forest lies 100 m from the home. You can dine out at the restaurants just 2 km away. Stock up your essentials from the local grocery store, 2 km from the home. The lake is 5 km from the home.You can relish a lovely cup of coffee in the garden with your dear ones. You can park your vehicles in the parking provided. You can stay inside comfortably with the central heating and fireplace provided. Child...
from $91 / night
Vacation Rental for 3 Guests in Chianti
Vacation Rental for 3 Guests in Chianti, Picture 1
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Vacation Rental for 3 Guests in Chianti, Picture 3
Vacation Rental for 3 Guests in Chianti, Picture 4
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Chianti
Vacation Rental • 538 ft² • 2 Bedrooms
8.4
(17 reviews)
Spend your holidays in this apartment with shared pool in the heart of Chianti Classico, near Greve in Chianti. Housed in a farm, the apartment is within walking distance of a medieval castle. This 2-bedroom apartment is ideal for families. Greve has so much to offer, including shops, restaurants and pizzerias. Its advantageous location in Chianti offers countless options for the most curious vacationers. A must visit are Panzano (8km), Radda (18 km), Gaiole (29 km), Castellina (19 km), Siena (46 km) or the enchanting Florence (32 km).The stone farm is surrounded by a garden. The apartment ...
from $83 / night

Popular Destinations in Chianti

    Prices and availability

    Current Vacation rental prices Chianti

    $288for 3 May - 10 May
    $305 annual average
    May
    Jun
    Jul
    Aug
    Sep
    Oct
    Nov
    Dec
    Jan
    Feb
    Mar
    Apr
    Average price per week

    Current vacation rental availability Chianti

    42%for 3 May - 10 May
    43% annual average
    May
    Jun
    Jul
    Aug
    Sep
    Oct
    Nov
    Dec
    Jan
    Feb
    Mar
    Apr
    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
    (2,247)
    Internet
    (2,560)
    Pets allowed
    (1,522)
    Balcony/Terrace
    (1,557)
    TV
    (2,114)
    Air conditioning
    (1,204)
    Yard
    (2,200)
    Parking
    (2,192)
    Washing machine
    (2,110)

    Vacation destinations in Chianti

    Vacation destinations nearby

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