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$ 44 - C$ 869C$ 869 - C$ 1,695C$ 1,695 - C$ 2,520C$ 2,520 - C$ 3,344C$ 3,344+ per night

Property Types

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Most recommended vacation rentals in Chianti

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La renaia - Cortona
La renaia
Cortona, TO, Italy
9.6Wonderful(242)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 142+
Check availability
I Rosai appartamento sulle colline fiorentine - Bagno a Ripoli - Kitchen
I Rosai appartamento sulle colline fiorentine
Bagno a Ripoli, TO, Italy
9.5Wonderful(114)
Parking
Free Wi-Fi
C$ 168+
Check availability
Country home in the Chiantishire close to Florence - Bagno a Ripoli
Country home in the Chiantishire close to Florence
Bagno a Ripoli, TO, Italy
10Wonderful(2)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 180+
Check availability
Il Palagetto - Bagno a Ripoli
Il Palagetto
Bagno a Ripoli, TO, Italy
8.9Very good(186)
Parking
Free Wi-Fi
Pool
C$ 275+
Check availability
Borgo dei Rosai - Bagno a Ripoli
Borgo dei Rosai
Bagno a Ripoli, TO, Italy
9.7Wonderful(15)
Parking
Free Wi-Fi
Pet friendly
C$ 277+
Check availability
The Small Castle - Cortona
The Small Castle
Cortona, TO, Italy
9.7Wonderful(24)
Free Wi-Fi
C$ 281+
Check availability
Casa Nobile - Together in Tuscany - Cortona
Casa Nobile - Together in Tuscany
Cortona, TO, Italy
8.8Very good(15)
Parking
Free Wi-Fi
C$ 305+
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Il Maggese - Cortona
Il Maggese
Cortona, TO, Italy
9.8Wonderful(51)
Parking
Free Wi-Fi
Pool
C$ 316+
Check availability
Florence Villa Violetta - Bagno a Ripoli - Patio
Florence Villa Violetta
Bagno a Ripoli, TO, Italy
9.9Wonderful(41)
Parking
Free Wi-Fi
C$ 323+
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La finestra sul Teatro - Cortona - Living room
La finestra sul Teatro
Cortona, TO, Italy
9.6Wonderful(160)
Parking
Free Wi-Fi
C$ 327+
Check availability
Willy - Sweet Dreams in Florence - Bagno a Ripoli - Bedroom
Willy - Sweet Dreams in Florence
Bagno a Ripoli, TO, Italy
8.4Very good(22)
Parking
Free Wi-Fi
C$ 364+
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Cortona Charme - Cortona - Bedroom
Cortona Charme
Cortona, TO, Italy
9.6Wonderful(14)
Parking
Free Wi-Fi
Pet friendly
C$ 369+
Check availability
La Terrazza - Together in Tuscany - Cortona - Living room
La Terrazza - Together in Tuscany
Cortona, TO, Italy
9.6Wonderful(29)
Parking
Free Wi-Fi
C$ 391+
Check availability
Faetole Typical Tuscan Country House Near Florence - Bagno a Ripoli - Bathroom
Faetole Typical Tuscan Country House Near Florence
Bagno a Ripoli, TO, Italy
9.8Wonderful(34)
Parking
Free Wi-Fi
Pet friendly
C$ 401+
Check availability
Luxury Suite apartment Angiolieri - Siena
Luxury Suite apartment Angiolieri
Siena, TO, Italy
9.0Wonderful(82)
Free Wi-Fi
C$ 512+
Check availability
Villa Franchetti - Luxurious Florentine Villa With Swimming Pool - Bagno a Ripoli - Bedroom
Villa Franchetti - Luxurious Florentine Villa With Swimming Pool
Bagno a Ripoli, TO, Italy
10Wonderful(7)
Free Wi-Fi
Pool
C$ 1,678+
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 C$ 416. The highest prices are found on Saturday, with average rates at C$ 1,231.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
October
C$ 249
C$ 232
Cheapest month to stay with an average 63% drop in price.
Most expensive month to stay with an average 12% 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$ 61. 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$ 1,574.

  • 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$ 6,745.

  • 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, campgrounds, barns, caravans, caravan parks, castles, chalets, condos, cottages, vacation villages, hotels, luxury tents 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 hu Firenze Camping in Town.

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

    There are a number of dog and pet-friendly Chianti vacation rentals, with around 16% 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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