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Holiday home & villa rental Tuscany Chianti

We have 235 properties to choose from
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House Montevarchi
410 m² house ∙ 22 guests ∙ 11 bedrooms

House Poggio Cuccule

Montevarchi, Province of Arezzo, Italy
from $486
per night
4.5
Excellent
(58 ratings)
from $486
per night
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Apartment Poggibonsi
130 m² apartment ∙ 9 guests ∙ 4 bedrooms

Apartment Il Forno

Poggibonsi, Province of Siena, Italy
from $198
per night
4.7
Excellent
(103 ratings)
from $198
per night
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House Bucine
500 m² house ∙ 29 guests ∙ 15 bedrooms

House Rosa+Margherita+Lavanda+Ginestra+Gelsomi

Bucine, Province of Arezzo, Italy
from $607
per night
4.5
Excellent
(4 ratings)
from $607
per night
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Apartment Poggibonsi
140 m² apartment ∙ 6 guests ∙ 3 bedrooms

Apartment Giuggiolo - Giuggiolo 5

Poggibonsi, Province of Siena, Italy
from $89
per night
4.3
Very good
(74 ratings)
from $89
per night
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House Greve in Chianti
210 m² house ∙ 12 guests ∙ 6 bedrooms

House Reggine

Greve in Chianti, Metropolitan City of Florence, Italy
from $318
per night
4.8
Outstanding
(18 ratings)
from $318
per night
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House Greve in Chianti
115 m² house ∙ 8 guests ∙ 3 bedrooms

House San Rocco

Greve in Chianti, Metropolitan City of Florence, Italy
from $193
per night
3.7
Good
(20 ratings)
from $193
per night
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Apartment Poggibonsi
130 m² apartment ∙ 6 guests ∙ 3 bedrooms

Apartment Giuggiolo 4

Poggibonsi, Province of Siena, Italy
from $89
per night
4.6
Excellent
(92 ratings)
from $89
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 $133
per night
4.6
Excellent
(36 ratings)
from $133
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 $186
per night
4.1
Very good
(23 ratings)
from $186
per night
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Farmhouse San Casciano in Val di Pesa
95 m² farmhouse ∙ 6 guests ∙ 3 bedrooms

Farmhouse Badia a Passignano

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from $148
per night
4.2
Very good
(66 ratings)
from $148
per night
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House San Gimignano
160 m² house ∙ 8 guests ∙ 4 bedrooms

House Le Sodole - Papavero e Pervinca

San Gimignano, Province of Siena, Italy
from $139
per night
3.2
(5 ratings)
from $139
per night
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House Rietine
70 m² house ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

Rietine, Gaiole in Chianti, Italy
from $74
per night
4.8
Outstanding
(15 ratings)
from $74
per night
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Farmhouse Castellina in Chianti
267 m² farmhouse ∙ 12 guests ∙ 6 bedrooms

Farmhouse Podere Gioia

Castellina in Chianti, Province of Siena, Italy
from $362
per night
4.9
Outstanding
(34 ratings)
from $362
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 $397
per night
4.5
Excellent
(43 ratings)
from $397
per night
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Farmhouse Cignan Bianco
130 m² farmhouse ∙ 9 guests ∙ 5 bedrooms

Farmhouse Cignanbianco - Alba e Tramonto

Cignan Bianco, Castellina in Chianti, Italy
from $182
per night
4.7
Excellent
(17 ratings)
from $182
per night
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Apartment Barberino Tavarnelle
62 m² 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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Apartment Greve in Chianti
40 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Mangiatoia

Greve in Chianti, Metropolitan City of Florence, Italy
from $94
per night
4.5
Excellent
(2 ratings)
from $94
per night
View deal
Farmhouse Tavarnelle Val di Pesa
70 m² farmhouse ∙ 5 guests ∙ 2 bedrooms

Farmhouse Il Casino

Tavarnelle Val di Pesa, Metropolitan City of Florence, Italy
from $95
per night
4.3
Very good
(31 ratings)
from $95
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 $170
per night
4.0
Very good
(13 ratings)
from $170
per night
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Farmhouse San Casciano in Val di Pesa
200 m² farmhouse ∙ 10 guests ∙ 5 bedrooms

Farmhouse Il Poggetto

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from $273
per night
4.4
Very good
(51 ratings)
from $273
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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Apartment Barberino Tavarnelle
from $124 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Petrarca

4.8
Outstanding(57 ratings)
Barberino Tavarnelle, Metropolitan City of Florence, Italy
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Farmhouse Poggibonsi
from $59 per night
Farmhouse ∙ 4 guests ∙ 1 bedroom

Farmhouse Giuggiolo - Giuggiolo 3

4.5
Excellent(49 ratings)
Poggibonsi, Province of Siena, Italy
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Vacation rentals with Wi-Fi

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

Apartment  Poggibonsi
from $100 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment Ciliegio

4.9
Outstanding(67 ratings)
Poggibonsi, Province of Siena, Italy
Internet
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Apartment  Poggibonsi
from $65 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.

Farmhouse  Monteriggioni
from $584 per night
Farmhouse ∙ 23 guests ∙ 9 bedrooms

Farmhouse Fattoria Petraglia

Monteriggioni, Province of Siena, Italy
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Farmhouse  Montevarchi
from $214 per night
Farmhouse ∙ 6 guests ∙ 3 bedrooms

Farmhouse Tegliaia

4.3
Very good(23 ratings)
Montevarchi, Province of Arezzo, Italy
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Farmhouse  Civitella in Val di Chiana
from $199 per night
Farmhouse ∙ 10 guests ∙ 5 bedrooms

Farmhouse Il Borgo di Gebbia

4.9
Outstanding(37 ratings)
Civitella in Val di Chiana, Province of Arezzo, 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.

Apartment  Castellina in Chianti
from $196 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment La Foresta

Castellina in Chianti, Province of Siena, Italy
Air conditioning
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House  Greve in Chianti
from $275 per night
House ∙ 12 guests ∙ 6 bedrooms

House Ridaldi

Greve in Chianti, Metropolitan City of Florence, Italy
Air conditioning
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House  Montevarchi
from $435 per night
House ∙ 12 guests ∙ 5 bedrooms

House Villa Lavinia

5.0
Outstanding(25 ratings)
Montevarchi, Province of Arezzo, 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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