Chianti vacation rentals

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Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from $49
San Gimignano
Vacation homes from $198
Cortona
Vacation homes from $106

Best Chianti vacation rentals

Villa in Castellina w. Pool, Garden & Winery - Castellina in Chianti - Living room
Villa in Castellina w. Pool, Garden & Winery
Castellina in Chianti, TO, Italy
10Wonderful(2)
Villa
$1,731+
Check availability
Separate Romantic 2br/2ba Cottage On Chianti Estate - Castellina in Chianti - Pool
Separate Romantic 2br/2ba Cottage On Chianti Estate
Castellina in Chianti, TO, Italy
8.0Very good(1)
Cottage
$326+
Check availability
Podere Lucignano Secondo Agriturismo - Gaiole In Chianti - Living room
Podere Lucignano Secondo Agriturismo
Gaiole In Chianti, TO, Italy
9.7Wonderful(89)
Villa
Parking
Free Wi-Fi
Pool
Pet friendly
$344+
Check availability
Chianti House - Gaiole In Chianti - Dining room
Chianti House
Gaiole In Chianti, TO, Italy
9.1Wonderful(6)
House
Parking
Free Wi-Fi
Pool
$253+
Check availability
Lindo Apartamento no coração do Chianti! - Castellina in Chianti - Patio
Lindo Apartamento no coração do Chianti!
Castellina in Chianti, TO, Italy
8.7Very good(6)
Apartment
Parking
Free Wi-Fi
Pool
$227+
Check availability
Agriturismo La Ferrozzola - Castellina in Chianti - Kitchen
Agriturismo La Ferrozzola
Castellina in Chianti, TO, Italy
9.1Wonderful(218)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
$145+
Check availability
Farmhouse in chianti with swimming pool ' Foresta 2' - Castellina in Chianti - Building
Farmhouse in chianti with swimming pool ' Foresta 2'
Castellina in Chianti, TO, Italy
9.1Wonderful(12)
Agritourism
$286+
Check availability
Azienda Agraria La Casella - Montalcino - Living room
Azienda Agraria La Casella
Montalcino, TO, Italy
9.1Wonderful(713)
Farm stay
Parking
Free Wi-Fi
Pet friendly
$160+
Check availability
Charming Chianti hilltop house, exceptional views, large swimming pool - Castellina in Chianti - Patio
Charming Chianti hilltop house, exceptional views, large swimming pool
Castellina in Chianti, TO, Italy
9.8Wonderful(13)
Agritourism
$308+
Check availability
Podere La Valle 9br, 16-20 Guests Retreats & Family In Restored Farm Spa & Pool - Castellina in Chianti - Living room
Podere La Valle 9br, 16-20 Guests Retreats & Family In Restored Farm Spa & Pool
Castellina in Chianti, TO, Italy
9.8Wonderful(26)
Villa
$1,579+
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Viticcio - Greve in Chianti
Viticcio
Greve in Chianti, TO, Italy
9.3Wonderful(809)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
$165+
Check availability
Mulino in Chianti - Gaiole In Chianti
Mulino in Chianti
Gaiole In Chianti, TO, Italy
9.4Wonderful(112)
Apartment
Parking
Free Wi-Fi
Pool
Pet friendly
$194+
Check availability
Ricasoli, Capanna Di Citerna - Gaiole In Chianti
Ricasoli, Capanna Di Citerna
Gaiole In Chianti, TO, Italy
10Wonderful(5)
Apartment
Parking
Free Wi-Fi
Pet friendly
$264+
Check availability
Ricasoli, Villa Agresto - Gaiole In Chianti
Ricasoli, Villa Agresto
Gaiole In Chianti, TO, Italy
Villa
Parking
Free Wi-Fi
Pool
Pet friendly
$1,048+
Check availability
Podere Sagna - Castellina in Chianti
Podere Sagna
Castellina in Chianti, TO, Italy
9.7Wonderful(107)
Apartment
Parking
Free Wi-Fi
Pool
Pet friendly
$153+
Check availability
Chianti wood - Gaiole In Chianti
Chianti wood
Gaiole In Chianti, TO, Italy
8.2Very good(34)
Apartment
Parking
Free Wi-Fi
Pet friendly
$205+
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?

Tuesday offers the lowest rates in Chianti, with an average nightly price of $186. 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)

November
February
$160
$118
Cheapest month to stay with an average 27% drop in price.
Most expensive month to stay with an average 76% 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 $44. 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 $1,204.

  • 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 $5,158.

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

  • 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 homes that can sleep 6 people or more by KAYAK users are Opera 19 Luxury Apartment and La Vecchia Firenze.

  • 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

Complete your trip to Chianti

Vacations in Chianti