Chianti vacation rentals

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Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from $34
San Gimignano
Vacation homes from $198
Montalcino
Vacation homes from $256
Siena
Vacation homes from $100

Best Chianti vacation rentals

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$32 - $477$477 - $923$923 - $1,368$1,368 - $1,813$1,813+ per night

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Most recommended vacation rentals in Chianti

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Agriturismo Albergotti - Arezzo - Bedroom
Agriturismo Albergotti
Arezzo, TO, Italy
9.6Wonderful(162)
Parking
Free Wi-Fi
Pool
$110+
Check availability
Agriturismo Podere Torre - Greve in Chianti
Agriturismo Podere Torre
Greve in Chianti, TO, Italy
9.4Wonderful(211)
Parking
Free Wi-Fi
Pool
$138+
Check availability
Podere II Colto - Located In A Beautiful Forested Area In Chianti Region heart - Gaiole In Chianti - Living room
Podere II Colto - Located In A Beautiful Forested Area In Chianti Region heart
Gaiole In Chianti, TO, Italy
$140+
Check availability
La Pievina - Montepulciano
La Pievina
Montepulciano, TO, Italy
9.7Wonderful(1683)
Parking
Free Wi-Fi
Pool
Pet friendly
$144+
Check availability
Appartamento Giulio - Bagno a Ripoli
Appartamento Giulio
Bagno a Ripoli, TO, Italy
9.4Wonderful(76)
Parking
Free Wi-Fi
Pool
$147+
Check availability
Apartment Quiet place by Interhome - Greve in Chianti
Apartment Quiet place by Interhome
Greve in Chianti, TO, Italy
8.5Very good(1)
Parking
Free Wi-Fi
$147+
Check availability
Pesci, Montefiorile, Gaiole in Chianti, Siena and Chianti - Gaiole In Chianti - Bedroom
Pesci, Montefiorile, Gaiole in Chianti, Siena and Chianti
Gaiole In Chianti, TO, Italy
9.5Wonderful(4)
$153+
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Borgo I Vicelli Adults Only Relais - Bagno a Ripoli - Living room
Borgo I Vicelli Adults Only Relais
Bagno a Ripoli, TO, Italy
9.1Wonderful(730)
Parking
Free Wi-Fi
Pool
Pet friendly
$179+
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Il Nibbio - Gaiole In Chianti - Living room
Il Nibbio
Gaiole In Chianti, TO, Italy
$201+
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Il rifugio dell'eroe - con piscina - Gaiole In Chianti
Il rifugio dell'eroe - con piscina
Gaiole In Chianti, TO, Italy
8.7Very good(7)
Parking
Free Wi-Fi
Pool
$202+
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Il Palagetto - Bagno a Ripoli
Il Palagetto
Bagno a Ripoli, TO, Italy
8.9Very good(179)
Parking
Free Wi-Fi
Pool
$210+
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Chianti chic - Gaiole In Chianti
Chianti chic
Gaiole In Chianti, TO, Italy
8.1Very good(27)
Parking
Free Wi-Fi
Pet friendly
$225+
Check availability
Country house on the Florence hills - Bagno a Ripoli - Bedroom
Country house on the Florence hills
Bagno a Ripoli, TO, Italy
10Wonderful(2)
Parking
Free Wi-Fi
Pet friendly
$235+
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2 Bedroom Nice Apartment In Arezzo - Arezzo - Bedroom
2 Bedroom Nice Apartment In Arezzo
Arezzo, TO, Italy
7.2Good(3)
Parking
Free Wi-Fi
$239+
Check availability
Apartment L'Angolo by Interhome - Bagno a Ripoli - Pool
Apartment L'Angolo by Interhome
Bagno a Ripoli, TO, Italy
Pool
$311+
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Il Matitone Family Home - Arezzo
Il Matitone Family Home
Arezzo, TO, Italy
9.5Wonderful(41)
Free Wi-Fi
$328+
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?

Sunday offers the lowest rates in Chianti, with an average nightly price of $220. The highest prices are found on Saturday, with average rates at $650.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

March
February
$162
$149
Cheapest month to stay with an average 36% drop in price.
Most expensive month to stay with an average 172% 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 $35. 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 $1,281.

  • 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 $5,490.

  • 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, cottages, farm stays, houses, villas, agritourism, barns, campgrounds, caravans, castles, chalets, condos, holiday parks, homestays, hotels, luxury tents, towers, caravan parks, lodges and cabins.

  • 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 hu Norcenni Girasole Village.

  • 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 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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Vacations in Chianti

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