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Holiday home & villa rental Tuscany Chianti

We have 244 properties to choose from
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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 $134
per night
4.6
Excellent
(36 ratings)
from $134
per night
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House Province of Arezzo
100 m² house ∙ 7 guests ∙ 3 bedrooms

House Il Forno

Province of Arezzo, Tuscany, Italy
from $188
per night
4.1
Very good
(23 ratings)
from $188
per night
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House San Casciano in Val di Pesa
House ∙ 6 guests ∙ 3 bedrooms

House Badia a Passignano

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from $149
per night
4.2
Very good
(66 ratings)
from $149
per night
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House Rietine
70 m² house ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

Rietine, Gaiole in Chianti, Italy
from $75
per night
4.8
Outstanding
(15 ratings)
from $75
per night
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House Montevarchi
House ∙ 22 guests ∙ 11 bedrooms

House Poggio Cuccule

Montevarchi, Province of Arezzo, Italy
from $489
per night
4.5
Excellent
(58 ratings)
from $489
per night
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House Bagno A Ripoli
270 m² house ∙ 12 guests ∙ 6 bedrooms

House Policleto

Bagno A Ripoli, Bagno a Ripoli, Italy
from $399
per night
4.5
Excellent
(43 ratings)
from $399
per night
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House Cignan Bianco
House ∙ 9 guests ∙ 5 bedrooms

House Cignanbianco - Alba e Tramonto

Cignan Bianco, Castellina in Chianti, Italy
from $183
per night
4.7
Excellent
(17 ratings)
from $183
per night
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House Castellina in Chianti
House ∙ 12 guests ∙ 6 bedrooms

House Podere Gioia

Castellina in Chianti, Province of Siena, Italy
from $364
per night
4.9
Outstanding
(34 ratings)
from $364
per night
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House Tavarnelle Val di Pesa
House ∙ 5 guests ∙ 2 bedrooms

House Il Casino

Tavarnelle Val di Pesa, Metropolitan City of Florence, Italy
from $96
per night
4.3
Very good
(31 ratings)
from $96
per night
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Apartment Barberino Tavarnelle
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Dante

Barberino Tavarnelle, Metropolitan City of Florence, Italy
from $150
per night
4.0
Very good
(1 rating)
from $150
per night
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House Certaldo
120 m² house ∙ 8 guests ∙ 4 bedrooms

House Conte Francesco II

Certaldo, Metropolitan City of Florence, Italy
from $171
per night
4.0
Very good
(13 ratings)
from $171
per night
View deal
House San Casciano in Val di Pesa
House ∙ 10 guests ∙ 5 bedrooms

House Il Poggetto

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from $275
per night
4.4
Very good
(51 ratings)
from $275
per night
View deal
Apartment Greve in Chianti
40 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Mangiatoia

Greve in Chianti, Metropolitan City of Florence, Italy
from $95
per night
4.5
Excellent
(2 ratings)
from $95
per night
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House Greve in Chianti
House ∙ 8 guests ∙ 4 bedrooms

House Ridaldi

Greve in Chianti, Metropolitan City of Florence, Italy
from $182
per night
4.2
Very good
(25 ratings)
from $182
per night
View deal
House Barberino Tavarnelle
110 m² house ∙ 5 guests ∙ 3 bedrooms

House Albachiara

Barberino Tavarnelle, Metropolitan City of Florence, Italy
from $164
per night
from $164
per night
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House San Casciano in Val di Pesa
House ∙ 4 guests ∙ 2 bedrooms

House Badia a Passignano

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from $88
per night
4.3
Very good
(18 ratings)
from $88
per night
View deal
House Poggibonsi
House ∙ 4 guests ∙ 1 bedroom

House Giuggiolo - Giuggiolo 2

Poggibonsi, Province of Siena, Italy
from $60
per night
4.5
Excellent
(53 ratings)
from $60
per night
View deal
House Rietine
70 m² house ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

Rietine, Gaiole in Chianti, Italy
from $76
per night
4.4
Very good
(21 ratings)
from $76
per night
View deal
House Radda in Chianti
House ∙ 10 guests ∙ 5 bedrooms

House Le Bonatte

Radda in Chianti, Province of Siena, Italy
from $278
per night
4.9
Outstanding
(53 ratings)
from $278
per night
View deal
House Pescina
95 m² house ∙ 6 guests ∙ 3 bedrooms

House Lucolena

Pescina, Greve in Chianti, Italy
from $155
per night
4.7
Excellent
(65 ratings)
from $155
per night
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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 Pescina
from $143 per night
House ∙ 6 guests ∙ 3 bedrooms

House Torsoli

4.6
Excellent(71 ratings)
Pescina, Greve in Chianti, Italy
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House Cavriglia
from $128 per night
House ∙ 8 guests ∙ 4 bedrooms

House Caiano

4.6
Excellent(66 ratings)
Cavriglia, Province of Arezzo, Italy
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House Certaldo
from $157 per night
House ∙ 6 guests ∙ 2 bedrooms

House Il Vallone

4.7
Excellent(54 ratings)
Certaldo, Metropolitan City of Florence, Italy
View deal

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  Castellina in Chianti
from $177 per night
House ∙ 6 guests ∙ 3 bedrooms

House Cerretino Oliveto

5.0
Outstanding(2 ratings)
Castellina in Chianti, Province of Siena, Italy
Air conditioning
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Apartment  Castellina in Chianti
from $197 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment La Foresta

Castellina in Chianti, Province of Siena, Italy
Air conditioning
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House  Certaldo
from $164 per night
House ∙ 6 guests ∙ 2 bedrooms

House Il Sorriso

5.0
Outstanding(26 ratings)
Certaldo, Metropolitan City of Florence, Italy
Air conditioning
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Vacation rentals with Wi-Fi

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

House  Monteriggioni
from $587 per night
House ∙ 23 guests ∙ 9 bedrooms

House Fattoria Petraglia

Monteriggioni, Province of Siena, Italy
Internet
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Apartment  Poggibonsi
from $66 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment Giuggiolo 6

4.2
Very good(35 ratings)
Poggibonsi, Province of Siena, Italy
Internet
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House  Rietine
from $76 per night
House ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

4.5
Excellent(17 ratings)
Rietine, Gaiole 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.

House  San Casciano in Val di Pesa
from $386 per night
House ∙ 12 guests ∙ 6 bedrooms

House Bulleri

3.9
Good(39 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
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House  Certaldo
from $171 per night
House ∙ 8 guests ∙ 4 bedrooms

House Conte Francesco I

3.9
Good(14 ratings)
Certaldo, Metropolitan City of Florence, Italy
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Apartment  Bucine
from $93 per night
Apartment ∙ 5 guests ∙ 3 bedrooms

Apartment Rosa

4.4
Very good(22 ratings)
Bucine, Province of Arezzo, Italy
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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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