Anytime
Guests
Anytime
Guests

Villas Tuscany Chianti to rent

We have 344 properties to choose from.
Show map
Show map
House Barberino Tavarnelle
110 m² house ∙ 5 guests ∙ 3 bedrooms

House Albachiara

Barberino Tavarnelle, Metropolitan City of Florence, Italy
from £123
per night
from £123
per night
View deal
House Castellina in Chianti
70 m² house ∙ 4 guests ∙ 2 bedrooms

House Cerretino Vigna

Castellina in Chianti, Province of Siena, Italy
from £110
per night
4.8
Outstanding
(6 ratings)
from £110
per night
View deal
House Greve in Chianti
170 m² house ∙ 8 guests ∙ 4 bedrooms

House Ridaldi

Greve in Chianti, Metropolitan City of Florence, Italy
from £141
per night
4.2
Very good
(26 ratings)
from £141
per night
View deal
House Poggibonsi
46 m² house ∙ 4 guests ∙ 1 bedroom

House Giuggiolo - Giuggioli 1

Poggibonsi, Province of Siena, Italy
from £45
per night
4.5
Excellent
(81 ratings)
from £45
per night
View deal
House Strada In Chianti
110 m² house ∙ 8 guests ∙ 4 bedrooms

House Pilar

Strada In Chianti, Greve in Chianti, Italy
from £138
per night
5.0
Outstanding
(2 ratings)
from £138
per night
View deal
House Colle di Val d'Elsa
90 m² house ∙ 4 guests ∙ 2 bedrooms

House Bardeggiano - Caterina 4 (COL247)

Colle di Val d'Elsa, Province of Siena, Italy
from £147
per night
4.6
Excellent
(9 ratings)
from £147
per night
View deal
House Tavarnelle Val di Pesa
70 m² house ∙ 5 guests ∙ 2 bedrooms

House Il Casino

Tavarnelle Val di Pesa, Metropolitan City of Florence, Italy
from £73
per night
4.3
Very good
(31 ratings)
from £73
per night
View deal
House San Casciano in Val di Pesa
200 m² house ∙ 10 guests ∙ 5 bedrooms

House Il Poggetto

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £205
per night
4.4
Very good
(51 ratings)
from £205
per night
View deal
House Certaldo
140 m² house ∙ 6 guests ∙ 2 bedrooms

House Decameron house

Certaldo, Metropolitan City of Florence, Italy
from £99
per night
3.8
Good
(13 ratings)
from £99
per night
View deal
House Civitella in Val di Chiana
300 m² house ∙ 10 guests ∙ 5 bedrooms

House Il Borgo di Gebbia

Civitella in Val di Chiana, Province of Arezzo, Italy
from £150
per night
4.9
Outstanding
(37 ratings)
from £150
per night
View deal
House San Casciano in Val di Pesa
95 m² house ∙ 6 guests ∙ 3 bedrooms

House Badia a Passignano

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £112
per night
4.2
Very good
(66 ratings)
from £112
per night
View deal
House Radda in Chianti
180 m² house ∙ 10 guests ∙ 5 bedrooms

House Le Bonatte

Radda in Chianti, Province of Siena, Italy
from £208
per night
4.9
Outstanding
(53 ratings)
from £208
per night
View deal
House Cavriglia
230 m² house ∙ 8 guests ∙ 4 bedrooms

House Caiano

Cavriglia, Province of Arezzo, Italy
from £96
per night
4.6
Excellent
(66 ratings)
from £96
per night
View deal
House Castellina in Chianti
267 m² house ∙ 12 guests ∙ 6 bedrooms

House Podere Gioia

Castellina in Chianti, Province of Siena, Italy
from £301
per night
4.9
Outstanding
(34 ratings)
from £301
per night
View deal
House Rietine
70 m² house ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

Rietine, Gaiole in Chianti, Italy
from £56
per night
4.4
Very good
(21 ratings)
from £56
per night
View deal
House Pescina
65 m² house ∙ 6 guests ∙ 3 bedrooms

House Torsoli

Pescina, Greve in Chianti, Italy
from £113
per night
4.6
Excellent
(71 ratings)
from £113
per night
View deal
Apartment Barberino Tavarnelle
62 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Dante

Barberino Tavarnelle, Metropolitan City of Florence, Italy
from £112
per night
4.0
Very good
(1 rating)
from £112
per night
View deal
House Greve in Chianti
210 m² house ∙ 12 guests ∙ 6 bedrooms

House Reggine

Greve in Chianti, Metropolitan City of Florence, Italy
from £239
per night
4.8
Outstanding
(18 ratings)
from £239
per night
View deal
House Province of Arezzo
100 m² house ∙ 7 guests ∙ 3 bedrooms

House Il Forno

Province of Arezzo, Tuscany, Italy
from £140
per night
4.1
Very good
(23 ratings)
from £140
per night
View deal
House Rietine
70 m² house ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

Rietine, Gaiole in Chianti, Italy
from £56
per night
4.8
Outstanding
(15 ratings)
from £56
per night
View deal

Top-Rated Lettings and Properties Chianti

Book Holiday Letting Offers with the Highest User Rating

House Gavignano
from £100 per night
House ∙ 4 guests ∙ 2 bedrooms

House Cedri Alti

4.7
Excellent(40 ratings)
Gavignano, Bucine, Italy
View deal
House San Gimignano
from £229 per night
House ∙ 8 guests ∙ 4 bedrooms

House Podere San Lorenzo

4.7
Excellent(38 ratings)
San Gimignano, Province of Siena, Italy
View deal
House Cignan Bianco
from £137 per night
House ∙ 9 guests ∙ 5 bedrooms

House Cignanbianco - Alba e Tramonto

4.7
Excellent(17 ratings)
Cignan Bianco, Castellina in Chianti, Italy
View deal

Holiday rentals with wifi

Stay connected in our holiday homes Chianti boasting high-speed WiFi during your stay.

House  Monteriggioni
from £438 per night
House ∙ 23 guests ∙ 9 bedrooms

House Fattoria Petraglia

Monteriggioni, Province of Siena, Italy
Internet
View deal
House  Greve in Chianti
from £68 per night
House ∙ 3 guests ∙ 1 bedroom

House San Rocco

3.8
Good(10 ratings)
Greve in Chianti, Metropolitan City of Florence, Italy
Internet
View deal
House  Poggibonsi
from £45 per night
House ∙ 4 guests ∙ 1 bedroom

House Giuggiolo - Giuggiolo 2

4.5
Excellent(53 ratings)
Poggibonsi, Province of Siena, Italy
Internet
View deal
See all offers

Holiday homes with parking

Experience hassle-free arrivals and departures with our holiday homes Chianti offering convenient parking access for your convenience.

House  Barberino Tavarnelle
from £208 per night
House ∙ 8 guests ∙ 4 bedrooms

House Campiglia

4.4
Very good(60 ratings)
Barberino Tavarnelle, Metropolitan City of Florence, Italy
View deal
House  Rietine
from £267 per night
House ∙ 12 guests ∙ 6 bedrooms

House Montechioccioli

5.0
Outstanding(3 ratings)
Rietine, Gaiole in Chianti, Italy
View deal
House  Barberino Val d'Elsa
from £144 per night
House ∙ 7 guests ∙ 3 bedrooms

House Linearis K

5.0
Outstanding(1 rating)
Barberino Val d'Elsa, Metropolitan City of Florence, Italy
View deal
See all offers

Cool comfort: accommodation with refreshing air-conditioning Chianti

Enjoy cool comfort in our holiday homes Chianti equipped with refreshing air conditioning for ultimate relaxation.

House  Greve in Chianti
from £211 per night
House ∙ 12 guests ∙ 6 bedrooms

House Ridaldi

Greve in Chianti, Metropolitan City of Florence, Italy
Air conditioning
View deal
House  Castellina in Chianti
from £132 per night
House ∙ 6 guests ∙ 3 bedrooms

House Cerretino Oliveto

5.0
Outstanding(2 ratings)
Castellina in Chianti, Province of Siena, Italy
Air conditioning
View deal
House  Certaldo
from £124 per night
House ∙ 6 guests ∙ 2 bedrooms

House Il Sorriso

5.0
Outstanding(26 ratings)
Certaldo, Metropolitan City of Florence, Italy
Air conditioning
View deal
See all offers

More travel options

Discover Chianti

The rich history and rustic charm of the region are beautifully reflected in the Chianti villa holiday homes. Often, these Chianti villas are renovated farmhouses, known as Agriturismi. They are constructed from stone or bricks, featuring terracotta roofs and spacious interiors adorned with rustic furniture. Chianti villas nestled amidst vineyards or olive groves are also highly sought after.

Tuscany Chianti - Best Top cities

San Gusmè

San Gusmè

The walled San Gusmè exudes medieval charm in its small winding alleys. You can visit two churches in the village, the Santissima Annunziata with its bell tower and the Church of Saints Cosimus and Damian. Then enjoy Tuscan snacks in one of the cafés.

San Donato in Poggio

San Donato in Poggio

The small San Donato in Poggio appears medieval with stone and brick houses. The place is surrounded by walls. The city gates Porta Fiorentina and Porta Senese, the old watchtower Torre Campanaria, and the Romanesque church Pieve di San Donato in Poggio with the bell tower bear witness to times gone by.

Montefiridolfi

Montefiridolfi

A cypress-lined path leads you along olive groves up to the small village of Montefiridolfi. The Etruscans already settled in the area. Montefiridolfi's earth-toned houses crown the typical Tuscan tiled roofs. From the village, you have a magnificent view of the surrounding hills.

Gaiole in Chianti

Gaiole in Chianti

In Tuscany, Gaiole in Chianti nestles gently into the vineyards of Siena. Around the center, numerous castles and palaces as well as churches and monasteries can be visited. Among them is the Brolio Castle from the 12th century, which offers a fantastic panoramic view.

Castellina in Chianti

Castellina in Chianti

Located on a hill, from Castellina in Chianti you overlook the Tuscan expanse with vineyards, cypresses, and pines. Romantic stone houses in Mediterranean style line the medieval streets of the town and invite you to stroll. Notable are the many small churches in the town, such as the medieval Chiesa di San Salvator.

Radda in Chianti

Radda in Chianti

Radda in Chianti sits atop a hill in the famous wine region of Chianti in Italy. The ancient city walls and fortifications bear witness to the medieval history. Stroll through cobblestone alleys and admire the impressive town hall from the 16th century, once known as Palazzo del Podesta.

Greve in Chianti

Greve in Chianti

The medieval town of Greve in Chianti in Italy is characterized by its medieval architecture, a testament to its over 1,000-year history. During a city tour, you will discover sights such as the romantic Church of Santa Croce, the Castle of Montefioralle, or the impressive Piazza. A lively market takes place every Saturday in the central square.

Tuscany Chianti - The most beautiful natural sights

Your villa in Chianti offers you the opportunity to explore the charming landscape and cultural heritage of the region. Begin your journey with the Bosco di Sant'Agnese nature reserve, located halfway between Poggibonsi and Castellina in Chianti. This area is home to a historic cypress grove and offers a fascinating landscape for hiking and mountain biking. The next highlight is the Chianti area, known for its vineyards and picturesque towns like Greve and Radda. Here you can taste fine wines and enjoy the breathtaking views from the wine road. Continue to Monte San Michele, the highest mountain in Chianti. The ascent begins at the exit of Badia a Montemuro and leads through lush Mediterranean landscapes to the summit. After enjoying the view, you can return the same way or take a mountain bike tour. The next stop is the Pesa Valley, which accompanies the river of the same name. Here you can visit the historic center of San Casciano Val di Pesa, surrounded by a 14th-century wall, or admire the Church of Santa Lucia al Borghetto in Tavernelle Val di Pesa. Conclude your journey with a visit to the Botanical Park in Chianti. This 5-hectare forest park is home to numerous species of wild plants and offers various activities such as guided tours, courses, and workshops. You can also visit the observatory with the largest telescope in Tuscany or participate in art exhibitions and open-air concerts.
Hand-picked and tested accommodation

Quality is our number one priority

Every property is checked before your arrival to ensure the best possible stay.

In-resort service and a 24/7 helpline

Make the most of our experience

Key collection is arranged by our helpful staff. Available 24/7 or on-site service to help you with all your questions, e.g.: tips and insights for your holiday destination and your booked accommodation.

A memorable holiday experience

Privacy and freedom in your own holiday homes

Be your own boss, eat whenever you want and make the most of plenty of space for all your friends and family.

image-tag