Chianti vacation rentals

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Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from $41
Cortona
Vacation homes from $106

Best Chianti vacation rentals

hu Firenze Camping in Town - Florence - Bedroom
hu Firenze Camping in Town
Campo di Marte
8.6Very good(14691)
Campground
Parking
Free Wi-Fi
Pool
Pet friendly
$59+
Check availability
Luxury Villa in Tuscany for 10 People - Radda In Chianti - Living room
Luxury Villa in Tuscany for 10 People
Radda In Chianti, TO, Italy
Villa
Free Wi-Fi
$4,742+
Check availability
Borgo I Vicelli Adults Only Relais - Bagno a Ripoli - Living room
Borgo I Vicelli Adults Only Relais
Bagno a Ripoli, TO, Italy
9.2Wonderful(736)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
$198+
Check availability
Agriturismo La Ferrozzola - Castellina in Chianti - Kitchen
Agriturismo La Ferrozzola
Castellina in Chianti, TO, Italy
9.1Wonderful(219)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
$145+
Check availability
Private Villa with A/C, WIFI, hot tub, sauna, private pool, TV, patio, close to Greve In Chianti - Radda In Chianti - Pool
Private Villa with A/C, WIFI, hot tub, sauna, private pool, TV, patio, close to Greve In Chianti
Radda In Chianti, TO, Italy
Villa
Free Wi-Fi
$4,539+
Check availability
Villa Al Bosco: An elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and by green hills, with Free WI-FI. - Radda In Chianti - Living room
Villa Al Bosco: An elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and by green hills, with Free WI-FI.
Radda In Chianti, TO, Italy
Villa
Free Wi-Fi
$1,533+
Check availability
Castello di Volpaia - Radda In Chianti - Restaurant
Castello di Volpaia
Radda In Chianti, TO, Italy
Agritourism
Pool
$253+
Check availability
Camping Village Il Poggetto - Florence - Pool
Camping Village Il Poggetto
Florence, TO, Italy
8.0Very good(1520)
Campground
Parking
Free Wi-Fi
Pool
Pet friendly
$36+
Check availability
Agriturismo La Posta Reale - Castiglion Fibocchi - Patio
Agriturismo La Posta Reale
Castiglion Fibocchi, TO, Italy
8.8Very good(160)
Farm stay
Parking
Free Wi-Fi
Pet friendly
$171+
Check availability
Wonderful villa for 6 people with WIFI, TV, terrace, pets allowed and panoramic view - Radda In Chianti - Balcony
Wonderful villa for 6 people with WIFI, TV, terrace, pets allowed and panoramic view
Radda In Chianti, TO, Italy
Villa
Free Wi-Fi
$304+
Check availability
Agriturismo San Lorenzo - Montepulciano
Agriturismo San Lorenzo
Montepulciano, TO, Italy
9.6Wonderful(417)
Farm stay
Parking
Free Wi-Fi
Pool
$138+
Check availability
Il Palagetto - Bagno a Ripoli
Il Palagetto
Bagno a Ripoli, TO, Italy
9.0Wonderful(177)
Apartment
Parking
Free Wi-Fi
Pool
$200+
Check availability
Az.Agr.Poggio Regini - Castellina in Chianti
Az.Agr.Poggio Regini
Castellina in Chianti, TO, Italy
8.5Very good(220)
Apartment
Parking
Free Wi-Fi
Pet friendly
$194+
Check availability
Il Moraiolo - Idromassaggio & Sauna con vista! - Loro Ciuffenna
Il Moraiolo - Idromassaggio & Sauna con vista!
Loro Ciuffenna, TO, Italy
9.7Wonderful(41)
House
Parking
Free Wi-Fi
Pool
Pet friendly
$797+
Check availability
Agriturismo Borgo Il Bonagino - Radda In Chianti
Agriturismo Borgo Il Bonagino
Radda In Chianti, TO, Italy
9.3Wonderful(118)
Farm stay
Parking
Free Wi-Fi
Pool
$261+
Check availability
Palazzo Bianciardi Attico - Castellina in Chianti
Palazzo Bianciardi Attico
Castellina in Chianti, TO, Italy
9.4Wonderful(48)
Apartment
Free Wi-Fi
$145+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
August
$161
$125
Cheapest month to stay with an average 28% drop in price.
Most expensive month to stay with an average 25% 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 $45. 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 $54 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 $1,161.

  • 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 $4,977.

  • 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 15% 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