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
Booking Insights
Recommended by KAYAK

Best Chianti holiday rentals

Most recommended holiday rentals in Chianti

Show all
Novella Italy - Florence - Bedroom
Novella Italy
Centro Storico
7.2Good(24)
Apartment
Free Wi-Fi
Camping Village Il Poggetto - Florence - Pool
Camping Village Il Poggetto
Florence, TO, Italy
7.9Good(1517)
Campground
Parking
Free Wi-Fi
Pool
Pet-friendly
hu Firenze Camping in Town - Florence - Bedroom
Parking
Free Wi-Fi
Pool
Pet-friendly
Camping Siena Colleverde - Siena - Pool
Parking
Free Wi-Fi
Pool
Pet-friendly
Fattoria Il Milione Agriturismo - Florence
Parking
Free Wi-Fi
Pool
Pet-friendly
Apartments Puccini - Florence - Living room
Free Wi-Fi
Air conditioning
hu Norcenni Girasole Village - Florence - Living room
Parking
Free Wi-Fi
Pool
Pet-friendly
Yome - Your Home in Florence - Florence
Free Wi-Fi
Air conditioning
Oltrarno 1881 Apartments - Florence
Free Wi-Fi
Air conditioning
Martelli 6 Suite & Apartments - Florence - Bedroom
Free Wi-Fi
Air conditioning
Il Frantoio Delle Grazie - Florence - Dining room
Parking
Free Wi-Fi
Pool
Pet-friendly
Numa Florence Fiore - Florence - Living room
Free Wi-Fi
Pet-friendly
Air conditioning
Mormoraia - San Gimignano - Bedroom
Mormoraia
San Gimignano, TO, Italy
Parking
Free Wi-Fi
Pool
Air conditioning
Capanna Suites - Montalcino - Pool
Capanna Suites
Montalcino, TO, Italy
Parking
Free Wi-Fi
Pool
Air conditioning
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?

Tuesday offers the lowest rates in Chianti, with an average nightly price of R3 192. The highest prices are found on Saturday, with average rates at R11 142.

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
January
R2 796
R2 883
Cheapest month to stay with an average 29% drop in price.
Most expensive month to stay with an average 36% 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 R861. 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 R753 per night. Search here for similar prices

  • 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, cottages, homestays, agritourism, towers, luxury tents, campgrounds, barns, caravans, castles, chalets, condos, campsites, hotels, lodges and cabins.

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

    If you’re looking for something special, the holiday rental most loved by KAYAK users is B&B La Coperta Ricamata.

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

    There are a number of dog and pet-friendly Chianti holiday 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 holiday home.

Everything you need to know for your stay in Chianti

Holiday rentals in Chianti