Chianti holiday rentals

Search hundreds of travel sites at once for holiday home deals in Chianti

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Latest Chianti holiday rental deals

MOST POPULARFlorence
Holiday homes from €181

Best Chianti holiday rentals

Most recommended holiday rentals in Chianti

Show all
hu Firenze Camping in Town - Florence - Bedroom
Parking
Free Wi-Fi
Pool
Pet friendly
Suites Roma 85 - Empoli
Free Wi-Fi
Pet friendly
Air conditioning
Appartamento Gori 2 - Siena
Parking
Free Wi-Fi
Pet friendly
Residenza Albalonga - Castelnuovo Berardenga
Residenza Albalonga
Castelnuovo Berardenga, TO, Italy
9.5Wonderful(33)
Parking
Free Wi-Fi
Air conditioning
Le Rondini, comfy flat - Empoli
Free Wi-Fi
Pet friendly
Air conditioning
Siena Hills Apartments - Siena - Restaurant
Parking
Free Wi-Fi
Pool
Pet friendly
La Casanuova - Lajatico
Parking
Free Wi-Fi
Pool
Pet friendly
Villa Viola - Chianciano Terme - Living room
Villa Viola
Chianciano Terme, TO, Italy
9.4Wonderful(76)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
Appartamento il Leone - Empoli
Parking
Free Wi-Fi
Pet friendly
Air conditioning
Duprè Apartment - Siena - Kitchen
Free Wi-Fi
Pet friendly
Air conditioning
Casale Collecchio Siena - Castelnuovo Berardenga
Casale Collecchio Siena
Castelnuovo Berardenga, TO, Italy
9.6Wonderful(16)
Parking
Free Wi-Fi
Air conditioning
Castello Di Bossi - Castelnuovo Berardenga
Castello Di Bossi
Castelnuovo Berardenga, TO, Italy
8.8Very Good(284)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
Borgo Serenità - Lajatico
Borgo Serenità
Lajatico, TO, Italy
7.3Good(3)
Free Wi-Fi
Air conditioning
Useful Info

Good to know

Low season

January

High season

December

Average price (weeknight)

€166

Average price (weekend night)

€243
Cheapest month to stay with an average 38% drop in price.
Most expensive month to stay with an average 33% 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 €55. 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 €62 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 €970.

  • 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 €4,156.

  • 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 agritourism, apartments, farm stays, houses, villas, homestays, towers, barns, campgrounds, 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 Coco Places Firenze, Centro Storico and Florence Apartments Home Feeling.

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

    There are a number of dog and pet-friendly Chianti holiday rentals, with around 20% 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.

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.