Vacation Rentals in Chianti
Start comparing over 6,981 rentals in Chianti and book at the best price!
Find offers
Child-friendly vacation rentals
1 bedroom
9.8
2 bedrooms
9.4
1 bedroom
8.6
5 bedrooms
9.2
Vacation rentals with pets allowed
Pets allowed
1 bedroom
9.2
Pets allowed
1 bedroom
10.0
Pets allowed
1 bedroom
7.0
Pets allowed
2 bedrooms
9.7
Vacation Rentals in Chianti
1 bedroom
9.0
1 bedroom
8.9
2 bedrooms
9.2
2 bedrooms
8.8
Vacation rentals with a lake view
Lake view
1 bedroom
10.0
Lake view
1 bedroom
10.0
Lake view
3 bedrooms
9.6
Lake view
1 bedroom
from $74 / nightFREE cancellationVacation rentals with free cancellation
1 bedroom
9.7
2 bedrooms
9.4
Great for families
At least 2 families rated this property and gave it an average score of 10.0/10
4 bedrooms
9.1
2 bedrooms
8.6
Current vacation rental deals in Chianti
Sun, 07/06 - Mon, 07/14
2 bedrooms
9.2
Special deal
FREE cancellationGreat find! Several discounts have been applied to the total price. View this offer to find out more.
Mon, 09/15 - Mon, 09/22
4 bedrooms
8.1
Special deal
FREE cancellationGreat find! Several discounts have been applied to the total price. View this offer to find out more.
Mon, 09/15 - Mon, 09/22
2 bedrooms
10.0
Special deal
FREE cancellationGreat find! Several discounts have been applied to the total price. View this offer to find out more.
Mon, 09/15 - Mon, 09/22
2 bedrooms
9.6
Special deal
FREE cancellationGreat find! Several discounts have been applied to the total price. View this offer to find out more.
Find Vacation Rentals in Chianti
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...
Chianti, Florence Province
Vacation Rental • 581 ft² • 1 Bedroom
Chianti, Florence Province
6.5
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 $65 / night
View offer
more...
Loro Ciuffenna, Chianti
Vacation Rental • 377 ft² • 1 Bedroom
Loro Ciuffenna, Chianti
9.4
This wonderful farmhouse with a bedroom is situated in Tuscany. It has one bedroom and can accommodate 2 guests. It is suitable for a couple on a romantic holiday, it offers a shared swimming pool ideal for relaxing hours.During your stay here, you can easily reach Gambassi Terme, Montignoso, Volterra, Siena, and Certaldo. While restaurants are 1.5 km away from the farmhouse, supermarkets can be found 3 km away.Here, you will find a living room where you can enjoy a TV in front of the fireplace. There is an open-plan kitchenette to cherish home-cooked food. This farmhouse is centrally heate...
from $87 / night
View offer
more...
Castelfranco Piandiscò (municipality), Chianti
Vacation Rental • 474 ft² • 1 Bedroom
Castelfranco Piandiscò (municipality), Chianti
8.0
This holiday home is a 1-bedroom apartment located on a farm, it can house up to 3 guests. It has free WiFi and a shared swimming pool on the premises. This holiday home is surrounded by forests and mountains, ideal for hiking. Visit the castles around Castello di Torre, Castello di Leccio and Castello di Sammezzano. There is a natural reserve in Reggello, Le Balze with beautiful cliffs. You can pay a visit to Masaccio Regello museum housing paintings from 15th-19th century. It is located at a distance of 30km from Arezzo and Florence and Siena is also easily accessible. It has a soccer f...
from $88 / night
View offer
Popular Destinations in Chianti
Prices and availability
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.
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 CastellinaCastellina 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 RaddaA 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.
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.