Chianti holiday rentals

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Latest Chianti holiday rental deals

MOST POPULARFlorence
Holiday homes from €181

Best Chianti holiday rentals

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€21 - €84€84 - €147€147 - €209€209 - €271€271+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Chianti

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Camping Village Il Poggetto - Florence - Pool
Camping Village Il Poggetto
Florence, TO, Italy
7.9Good(1443)
Parking
Free Wi-Fi
Pool
Pet friendly
€43+
Check availability
hu Norcenni Girasole Village - Florence - Living room
hu Norcenni Girasole Village
Florence, TO, Italy
8.5Very Good(1720)
Parking
Free Wi-Fi
Pool
Pet friendly
€45+
Check availability
Novella Italy - Florence - Bedroom
Novella Italy
Centro Storico
7.2Good(22)
Free Wi-Fi
€58+
Check availability
Camping Siena Colleverde - Siena - Pool
Camping Siena Colleverde
Siena, TO, Italy
8.1Very Good(2906)
Parking
Free Wi-Fi
Pool
Pet friendly
€61+
Check availability
Urban central Florence - Florence
Urban central Florence
Campo di Marte
5.1Fair(665)
€85+
Check availability
hu Firenze Camping in Town - Florence - Bedroom
hu Firenze Camping in Town
Campo di Marte
8.6Very Good(14115)
Parking
Free Wi-Fi
Pool
Pet friendly
€94+
Check availability
Apartments Puccini - Florence - Living room
Apartments Puccini
Centro Storico
8.3Very Good(431)
Free Wi-Fi
Air conditioning
€109+
Check availability
Il Frantoio Delle Grazie - Florence - Dining room
Il Frantoio Delle Grazie
Campo di Marte
8.4Very Good(311)
Parking
Free Wi-Fi
Pool
Pet friendly
€147+
Check availability
Regis Condo - Siena - Bedroom
Regis Condo
Siena, TO, Italy
9.1Wonderful(856)
Free Wi-Fi
Pet friendly
Air conditioning
€173+
Check availability
Flospirit - Santissima Annunziata - Florence - Dining room
Flospirit - Santissima Annunziata
Centro Storico
8.1Very Good(40)
Free Wi-Fi
€180+
Check availability
Yome - Your Home in Florence - Florence
Yome - Your Home in Florence
Centro Storico
7.8Good(2382)
Free Wi-Fi
Air conditioning
€196+
Check availability
Rocca di Castagnoli - Gaiole In Chianti - Bedroom
Rocca di Castagnoli
Gaiole In Chianti, TO, Italy
8.4Very Good(456)
Parking
Free Wi-Fi
Pool
Pet friendly
€211+
Check availability
Fattoria di Corsignano - Castelnuovo Berardenga - Pool
Fattoria di Corsignano
Castelnuovo Berardenga, TO, Italy
8.3Very Good(393)
Parking
Free Wi-Fi
Pool
Pet friendly
€218+
Check availability
Numa Florence Fiore - Florence - Living room
Numa Florence Fiore
Centro Storico
9.1Wonderful(1058)
Free Wi-Fi
Pet friendly
Air conditioning
€298+
Check availability
Mormoraia - San Gimignano - Bedroom
Mormoraia
San Gimignano, TO, Italy
9.3Wonderful(1878)
Parking
Free Wi-Fi
Pool
Air conditioning
€345+
Check availability
Capanna Suites - Montalcino - Pool
Capanna Suites
Montalcino, TO, Italy
9.5Wonderful(585)
Parking
Free Wi-Fi
Pool
Air conditioning
€462+
Check availability
Booking Insights

KAYAK’s insights for holiday 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 €160. The highest prices are found on Saturday, with average rates at €472.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
August
€144
€136
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 1% 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 holiday home in Chianti

  • How much is a holiday rental in Chianti for tonight?

    In the last 72 hours, users have found Chianti holiday rentals for tonight for as little as €39. Search here for similar prices

  • How much is a holiday rental in Chianti for this weekend?

    In the last 72 hours, users have found Chianti holiday rentals for this weekend for as little as €37 per night. Search here for similar prices

  • How much is a holiday rental for a week in Chianti?

    The average price for a weekly Chianti holiday rental found by KAYAK users in the last 2 weeks is €998.

  • How much is a holiday rental for a month in Chianti?

    The average price for a monthly Chianti holiday rental found by KAYAK users in the last 2 weeks is €4,279.

  • What types of holiday rentals are available in Chianti?

    There are loads of different property types that you can make your holiday home in Chianti. You’ll find apartments, farm stays, houses, villas, agritourism, towers, homestays, campgrounds, barns, caravans, caravan parks, castles, chalets, condos, cottages, campsites, luxury tents and lodges.

  • What are some of the most-loved holiday rentals available in Chianti?

    There are many types of properties available for Chianti holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Agriturismo Il Casolare Di Bucciano and Il Frantoio Delle Grazie.

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

    There are a number of dog and pet-friendly Chianti holiday rentals, with around 17% 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 holiday home.

Everything you need to know for your stay in Chianti

Holiday rentals in Chianti

Florence holiday rentals

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