Chianti vacation rentals

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Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from $60
Montepulciano
Vacation homes from $256
San Gimignano
Vacation homes from $198
Montalcino
Vacation homes from $256
Siena
Vacation homes from $100

Best Chianti vacation rentals

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$23 - $181$181 - $338$338 - $495$495 - $652$652+ per night

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ApartmentHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Chianti

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Agricampeggio Borgo Agna - San Giustino Valdarno
Agricampeggio Borgo Agna
San Giustino Valdarno, TO, Italy
9.5Wonderful(9)
Parking
Free Wi-Fi
Pet friendly
$34+
Check availability
La Dimora dell'Alfiere - San Quirico d'Orcia
La Dimora dell'Alfiere
San Quirico d'Orcia, TO, Italy
8.9Very good(6)
Parking
Free Wi-Fi
Pet friendly
$125+
Check availability
Bella casa vicino alla grotta giusti. - Monsummano Terme
Bella casa vicino alla grotta giusti.
Monsummano Terme, TO, Italy
9.3Wonderful(13)
Parking
$140+
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La casa di Sophie - Bagno a Ripoli
La casa di Sophie
Bagno a Ripoli, TO, Italy
9.8Wonderful(10)
Parking
Free Wi-Fi
$147+
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Tuscan Sun Studios - Florence - Bedroom
Tuscan Sun Studios
Centro Storico
8.1Very good(55)
Free Wi-Fi
$156+
Check availability
Villa Buonasera Agriturismo - Greve in Chianti
Villa Buonasera Agriturismo
Greve in Chianti, TO, Italy
8.4Very good(183)
Parking
Free Wi-Fi
Pool
Pet friendly
$158+
Check availability
Castello di Fulignano Soarzio panoramic apartment - San Gimignano
Castello di Fulignano Soarzio panoramic apartment
San Gimignano, TO, Italy
9.1Wonderful(43)
Parking
Free Wi-Fi
Pool
Pet friendly
$163+
Check availability
Casa della Fonte - San Quirico d'Orcia
Casa della Fonte
San Quirico d'Orcia, TO, Italy
8.9Very good(307)
Parking
Free Wi-Fi
Pet friendly
$165+
Check availability
Castellino4Holidays - Monteriggioni
Castellino4Holidays
Monteriggioni, TO, Italy
8.7Very good(95)
Parking
Free Wi-Fi
Pool
Pet friendly
$180+
Check availability
Willy - Sweet Dreams in Florence - Bagno a Ripoli - Bedroom
Willy - Sweet Dreams in Florence
Bagno a Ripoli, TO, Italy
8.8Very good(19)
Parking
Free Wi-Fi
$193+
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Roommo Beccaria - Florence
Roommo Beccaria
Campo di Marte
8.4Very good(77)
Free Wi-Fi
Pet friendly
$199+
Check availability
Sadio Artemio Franchi shine apartment with terrace - Florence
Sadio Artemio Franchi shine apartment with terrace
Campo di Marte
7.2Good(4)
Free Wi-Fi
Pet friendly
$200+
Check availability
Appartamenti Ava E Tegrino Nell'antica Dimora Di Fulignano - San Gimignano
Appartamenti Ava E Tegrino Nell'antica Dimora Di Fulignano
San Gimignano, TO, Italy
9.4Wonderful(150)
Parking
Free Wi-Fi
Pool
Pet friendly
$216+
Check availability
Romantic cottage on a farm with a view of Cortona - Cortona - Outdoors view
Romantic cottage on a farm with a view of Cortona
Cortona, TO, Italy
Pool
Pet friendly
$267+
Check availability
Agriturismo Fattoria Di Maiano - Settignano
Agriturismo Fattoria Di Maiano
Settignano, TO, Italy
8.8Very good(641)
Parking
Free Wi-Fi
Pool
Pet friendly
$290+
Check availability
'Le Cure Home' Appartamento con 2 Camere Matrimoniali, Terrazzo - Florence
'Le Cure Home' Appartamento con 2 Camere Matrimoniali, Terrazzo
San Giovanni
9.1Wonderful(47)
Parking
Free Wi-Fi
$405+
Check availability
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Good to know

Low season

March

High season

December

Average price (weeknight)

$260

Average price (weekend night)

$282
Cheapest month to stay with an average 38% drop in price.
Most expensive month to stay with an average 27% 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 $64. 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 $1,457.

  • 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 $6,243.

  • 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 apartments, houses, agritourism, barns, campgrounds, caravans, caravan parks, castles, chalets, condos, cottages, farm stays, holiday parks, homestays, luxury tents, towers, villas 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 Camping Village Il Poggetto and Lupaia.

  • What are the most popular Chianti vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation home that can sleep 6 people or more by KAYAK users is Opera 19 Luxury Apartment.

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

    There are a number of dog and pet-friendly Chianti vacation rentals, with around 20% 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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Vacations in Chianti

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