Chianti vacation rentals

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Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from C$ 118

Best Chianti vacation rentals

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C$ 43 - C$ 144C$ 144 - C$ 245C$ 245 - C$ 346C$ 346 - C$ 445C$ 445+ per night

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Most recommended vacation rentals in Chianti

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Appartamento Grey - Arezzo
Appartamento Grey
Arezzo, TO, Italy
9.5Wonderful(381)
Parking
Free Wi-Fi
Pool
C$ 134+
Check availability
Podere Mezzastrada - Place of Charme - San Casciano Val Di Pesa - Dining room
Podere Mezzastrada - Place of Charme
San Casciano Val Di Pesa, TO, Italy
8.7Very good(808)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 142+
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Farmhouse Il Canneto apartment near Siena and San Gimignano - Siena
Farmhouse Il Canneto apartment near Siena and San Gimignano
Siena, TO, Italy
C$ 150+
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Vasari Home - Arezzo
Vasari Home
Arezzo, TO, Italy
8.6Very good(67)
Free Wi-Fi
Pet friendly
C$ 154+
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Villa Nottola - Montepulciano
Villa Nottola
Montepulciano, TO, Italy
9.0Wonderful(1800)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 177+
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Agriturismo Podere Torre - Greve in Chianti
Agriturismo Podere Torre
Greve in Chianti, TO, Italy
9.4Wonderful(211)
Parking
Free Wi-Fi
Pool
C$ 178+
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Agriturismo Fattoria Santo Stefano - Greve in Chianti
Agriturismo Fattoria Santo Stefano
Greve in Chianti, TO, Italy
9.1Wonderful(217)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 182+
Check availability
Agriturismo Lucciano - San Casciano Val Di Pesa
Agriturismo Lucciano
San Casciano Val Di Pesa, TO, Italy
8.8Very good(66)
Parking
Free Wi-Fi
Pet friendly
C$ 196+
Check availability
La Rimbecca Greve in Chianti - Greve in Chianti
La Rimbecca Greve in Chianti
Greve in Chianti, TO, Italy
9.3Wonderful(657)
Parking
Free Wi-Fi
Pool
C$ 247+
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Casa Ercole Farm Stay - Greve in Chianti
Casa Ercole Farm Stay
Greve in Chianti, TO, Italy
9.5Wonderful(138)
Parking
Free Wi-Fi
C$ 248+
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Podere Papèra - Chianti hills - San Casciano Val Di Pesa
Podere Papèra - Chianti hills
San Casciano Val Di Pesa, TO, Italy
9.0Wonderful(6)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 255+
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Apartment 3 people vico alto - Siena - Pool
Apartment 3 people vico alto
Siena, TO, Italy
C$ 263+
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Chianti Home with Pool Terrace Garden and Magnificient View 2 to 8 persons - Greve in Chianti
Chianti Home with Pool Terrace Garden and Magnificient View 2 to 8 persons
Greve in Chianti, TO, Italy
8.3Very good(15)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 268+
Check availability
Agriturismo Merigge Wellness & Spa Montepulciano - Montepulciano - Bedroom
Agriturismo Merigge Wellness & Spa Montepulciano
Montepulciano, TO, Italy
9.6Wonderful(256)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 345+
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Il Fienile del Vichiaccio - San Casciano Val Di Pesa
Il Fienile del Vichiaccio
San Casciano Val Di Pesa, TO, Italy
10Wonderful(36)
Parking
Free Wi-Fi
Pet friendly
C$ 378+
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Entro Le Mura - Montepulciano
Entro Le Mura
Montepulciano, TO, Italy
9.3Wonderful(48)
Free Wi-Fi
C$ 622+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Chianti

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chianti with confidence.

What is the cheapest day of the week to book a vacation rental in Chianti?

Thursday offers the lowest rates in Chianti, with an average nightly price of C$ 285. The highest prices are found on Saturday, with average rates at C$ 911.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
August
C$ 250
C$ 260
Cheapest month to stay with an average 29% drop in price.
Most expensive month to stay with an average 18% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a vacation home in Chianti

  • How much is a vacation rental in Chianti for tonight?

    In the last 72 hours, users have found Chianti vacation rentals for tonight for as low as C$ 63. Search here for similar prices

  • How much is a vacation rental in Chianti for this weekend?

    In the last 72 hours, users have found Chianti vacation rentals for this weekend for as low as C$ 64 per night. Search here for similar prices

  • How much is a vacation rental for a week in Chianti?

    The average price for a weekly Chianti vacation rental found by KAYAK users in the last 2 weeks is C$ 1,433.

  • How much is a vacation rental for a month in Chianti?

    The average price for a monthly Chianti vacation rental found by KAYAK users in the last 2 weeks is C$ 6,141.

  • What types of vacation rentals are available in Chianti?

    There are loads of different property types that you can make your vacation home in Chianti. You’ll find agritourism, apartments, farm stays, villas, houses, towers, homestays, luxury tents, campgrounds, barns, caravans, castles, chalets, condos, cottages, vacation villages, hotels, caravan parks and lodges.

  • What are some of the most-loved vacation rentals available in Chianti?

    There are many types of properties available for Chianti vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are hu Firenze Camping in Town and Camping Village Il Poggetto.

  • Are there any pet-friendly vacation rentals in Chianti?

    There are a number of dog and pet-friendly Chianti vacation rentals, with around 14% allowing you to bring your pet along with you.

Where to stay in Chianti?

Our map will help you find the perfect place to stay in Chianti by showing you the exact location of each vacation home.

Everything you need to know for your stay in Chianti

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