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Holiday home & villa rental Tuscany Chianti

We have 333 properties to choose from
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House Radda in Chianti
180 m² house ∙ 10 guests ∙ 5 bedrooms

House Le Bonatte

Radda in Chianti, Province of Siena, Italy
from $267
per night
4.9
Outstanding
(57 ratings)
from $267
per night
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House Cignan Bianco
130 m² house ∙ 9 guests ∙ 5 bedrooms

House Cignanbianco - Alba e Tramonto

Cignan Bianco, Castellina in Chianti, Italy
from $170
per night
4.8
Outstanding
(9 ratings)
from $170
per night
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House Greve in Chianti
95 m² house ∙ 6 guests ∙ 3 bedrooms

House Lucolena

Greve in Chianti, Metropolitan City of Florence, Italy
from $164
per night
4.7
Excellent
(69 ratings)
from $164
per night
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House San Gimignano
190 m² house ∙ 8 guests ∙ 4 bedrooms

House Podere San Lorenzo

San Gimignano, Province of Siena, Italy
from $257
per night
4.7
Excellent
(40 ratings)
from $257
per night
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House Cavallari
120 m² house ∙ 6 guests ∙ 2 bedrooms

House Olimpia

Cavallari, Castellina in Chianti, Italy
from $290
per night
from $290
per night
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House Cavriglia
230 m² house ∙ 8 guests ∙ 4 bedrooms

House Caiano

Cavriglia, Province of Arezzo, Italy
from $118
per night
4.6
Excellent
(71 ratings)
from $118
per night
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House Bucine
160 m² house ∙ 8 guests ∙ 4 bedrooms

House Villa I Gelsomini

Bucine, Province of Arezzo, Italy
from $138
per night
4.3
Very good
(28 ratings)
from $138
per night
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House Tavarnelle Val di Pesa
100 m² house ∙ 6 guests ∙ 3 bedrooms

House Casa Fitzy

Tavarnelle Val di Pesa, Metropolitan City of Florence, Italy
from $132
per night
4.6
Excellent
(40 ratings)
from $132
per night
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House Castellina in Chianti
70 m² house ∙ 4 guests ∙ 2 bedrooms

House Cerretino Vigna

Castellina in Chianti, Province of Siena, Italy
from $138
per night
4.8
Outstanding
(6 ratings)
from $138
per night
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House Greve in Chianti
120 m² house ∙ 4 guests ∙ 2 bedrooms

House Casa Aia

Greve in Chianti, Metropolitan City of Florence, Italy
from $339
per night
5.0
Outstanding
(1 rating)
from $339
per night
View deal
House San Casciano in Val di Pesa
40 m² house ∙ 4 guests ∙ 2 bedrooms

House Badia a Passignano

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from $117
per night
4.2
Very good
(22 ratings)
from $117
per night
View deal
House Castelnuovo Berardenga
110 m² house ∙ 6 guests ∙ 2 bedrooms

House Vanessa

Castelnuovo Berardenga, Province of Siena, Italy
from $115
per night
4.7
Excellent
(94 ratings)
from $115
per night
View deal
House Certaldo
80 m² house ∙ 6 guests ∙ 2 bedrooms

House Il Sorriso

Certaldo, Metropolitan City of Florence, Italy
from $113
per night
5.0
Outstanding
(33 ratings)
from $113
per night
View deal
Apartment Poggibonsi
130 m² apartment ∙ 6 guests ∙ 3 bedrooms

Apartment Giuggiolo 4

Poggibonsi, Province of Siena, Italy
from $94
per night
4.6
Excellent
(79 ratings)
from $94
per night
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House Gavignano
55 m² house ∙ 4 guests ∙ 2 bedrooms

House Cedri Alti

Gavignano, Bucine, Italy
from $144
per night
4.7
Excellent
(39 ratings)
from $144
per night
View deal
House Greve in Chianti
65 m² house ∙ 4 guests ∙ 2 bedrooms

House Chiesa

Greve in Chianti, Metropolitan City of Florence, Italy
from $86
per night
4.4
Very good
(22 ratings)
from $86
per night
View deal
Apartment Barberino Tavarnelle
62 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Dante

Barberino Tavarnelle, Metropolitan City of Florence, Italy
from $149
per night
4.7
Excellent
(20 ratings)
from $149
per night
View deal
Apartment Greve in Chianti
55 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment L'Angolo di Uzzano

Greve in Chianti, Metropolitan City of Florence, Italy
from $133
per night
4.9
Outstanding
(59 ratings)
from $133
per night
View deal
House Castellina in Chianti
107 m² house ∙ 6 guests ∙ 3 bedrooms

House Cerretino Oliveto

Castellina in Chianti, Province of Siena, Italy
from $167
per night
5.0
Outstanding
(16 ratings)
from $167
per night
View deal
House Montevarchi
155 m² house ∙ 10 guests ∙ 5 bedrooms

House Tegliaia

Montevarchi, Province of Arezzo, Italy
from $273
per night
4.7
Excellent
(12 ratings)
from $273
per night
View deal

Top-Rated Vacation rentals Chianti

Book the highest-rated Chianti vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House San Casciano in Val di Pesa
from $293 per night
House ∙ 8 guests ∙ 4 bedrooms

House Ambrogetta

4.8
Outstanding(105 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
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Apartment Castellina in Chianti
from $111 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment La Tinaia

4.7
Excellent(66 ratings)
Castellina in Chianti, Province of Siena, Italy
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House Certaldo
from $156 per night
House ∙ 6 guests ∙ 2 bedrooms

House Il Vallone

4.7
Excellent(63 ratings)
Certaldo, Metropolitan City of Florence, Italy
View deal

Vacation rentals with Wi-Fi

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

House  San Regolo
from $201 per night
House ∙ 4 guests ∙ 2 bedrooms

House San Regolo

San Regolo, Gaiole in Chianti, Italy
Internet
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House  Radda in Chianti
from $412 per night
House ∙ 14 guests ∙ 7 bedrooms

House Le Bonatte

4.5
Excellent(7 ratings)
Radda in Chianti, Province of Siena, Italy
Internet
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House  Cignan Bianco
from $80 per night
House ∙ 3 guests ∙ 2 bedrooms

House Cignanbianco - Alba

4.5
Excellent(62 ratings)
Cignan Bianco, Castellina in Chianti, Italy
Internet
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Vacation houses with Parking

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

Apartment  Bucine
from $74 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Arco

4.4
Very good(38 ratings)
Bucine, Province of Arezzo, Italy
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House  Montevarchi
from $487 per night
House ∙ 22 guests ∙ 11 bedrooms

House Poggio Cuccule

4.5
Excellent(58 ratings)
Montevarchi, Province of Arezzo, Italy
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House  Greve in Chianti
from $169 per night
House ∙ 8 guests ∙ 3 bedrooms

House San Rocco

3.5
Good(49 ratings)
Greve in Chianti, Metropolitan City of Florence, Italy
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Cool comfort: accommodation with refreshing air-conditioning Chianti

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

House  San Gimignano
from $229 per night
House ∙ 7 guests ∙ 4 bedrooms

House Il Sangiovese

4.0
Very good(47 ratings)
San Gimignano, Province of Siena, Italy
Air conditioning
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House  Rietine
from $89 per night
House ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

4.7
Excellent(17 ratings)
Rietine, Gaiole in Chianti, Italy
Air conditioning
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House  Poggibonsi
from $145 per night
House ∙ 6 guests ∙ 3 bedrooms

House Villa Angiolino

5.0
Outstanding(25 ratings)
Poggibonsi, Province of Siena, Italy
Air conditioning
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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.
Only selected and tested accommodation

Quality is our number one priority

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

Guaranteed availability and on-site service

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

Flexible Booking Options

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

Why Interhome?

It has never been easier to find your perfect holiday. Do you want to explore new travel destinations? There is no better way than doing it in a holiday home: Enjoy "la dolce vita" in Italy, feel the charming lifestyle of the French Riviera or the Spanish way of life. Be inspired by our travel ideas and book online - quick, easy, and secure with Interhome.

Freedom, privacy and space in your holiday home

Your stay in a holiday house or a holiday apartment offers plenty of advantages: spend your time exactly as you want. No disturbance from other guests or hotel staff, just spend your holiday according to your own rules. Whether you are looking for a city trip, a relaxing holiday with your family or with friends. Simply enjoy lots of room, flexibility and freedom in your holiday home.

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