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

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

R536 - R1 781R1 781 - R3 026R3 026 - R4 271R4 271 - R5 499R5 499+ per night

Property Types

ApartmentHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Chianti

Show all
Agriturismo Albergotti - Arezzo - Bedroom
Agriturismo Albergotti
Arezzo, TO, Italy
9.6Wonderful(162)
Parking
Free Wi-Fi
Pool
R1 902+
Check availability
Agriturismo La Torricella - Pistoia - Pool
Agriturismo La Torricella
Pistoia, TO, Italy
8.6Very Good(127)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 058+
Check availability
Agriturismo Podere Torre - Greve in Chianti
Agriturismo Podere Torre
Greve in Chianti, TO, Italy
9.4Wonderful(211)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 196+
Check availability
La Pievina - Montepulciano
La Pievina
Montepulciano, TO, Italy
9.7Wonderful(1684)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 386+
Check availability
Villa Augusto - Cortona - Bedroom
Villa Augusto
Cortona, TO, Italy
9.4Wonderful(208)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 577+
Check availability
Appartamento Giulio - Bagno a Ripoli
Appartamento Giulio
Bagno a Ripoli, TO, Italy
9.4Wonderful(76)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 650+
Check availability
Apartment Quiet place by Interhome - Greve in Chianti
Apartment Quiet place by Interhome
Greve in Chianti, TO, Italy
8.5Very Good(1)
Parking
Free Wi-Fi
Air conditioning
R2 749+
Check availability
Borgo I Vicelli Adults Only Relais - Bagno a Ripoli - Living room
Borgo I Vicelli Adults Only Relais
Bagno a Ripoli, TO, Italy
9.1Wonderful(730)
Parking
Free Wi-Fi
Pool
Pet-friendly
R3 055+
Check availability
Il Palagetto - Bagno a Ripoli
Il Palagetto
Bagno a Ripoli, TO, Italy
8.9Very Good(179)
Parking
Free Wi-Fi
Pool
R3 628+
Check availability
Florence Villa Violetta - Bagno a Ripoli - Patio
Florence Villa Violetta
Bagno a Ripoli, TO, Italy
9.9Wonderful(43)
Parking
Free Wi-Fi
Air conditioning
R4 046+
Check availability
Country house on the Florence hills - Bagno a Ripoli - Bedroom
Country house on the Florence hills
Bagno a Ripoli, TO, Italy
10Wonderful(2)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R4 067+
Check availability
2 Bedroom Nice Apartment In Arezzo - Arezzo - Bedroom
2 Bedroom Nice Apartment In Arezzo
Arezzo, TO, Italy
7.2Good(3)
Parking
Free Wi-Fi
Air conditioning
R4 133+
Check availability
Apartment L'Angolo by Interhome - Bagno a Ripoli - Pool
Apartment L'Angolo by Interhome
Bagno a Ripoli, TO, Italy
Pool
Air conditioning
R5 344+
Check availability
L'Arrampicata by Interhome - Bagno a Ripoli - Living room
L'Arrampicata by Interhome
Bagno a Ripoli, TO, Italy
8.6Very Good(3)
Air conditioning
R5 555+
Check availability
Il Matitone Family Home - Arezzo
Il Matitone Family Home
Arezzo, TO, Italy
9.5Wonderful(41)
Free Wi-Fi
Air conditioning
R6 363+
Check availability
Il Tuo Posto A Greve In Chianti - Greve in Chianti - Living room
Il Tuo Posto A Greve In Chianti
Greve in Chianti, TO, Italy
10Wonderful(2)
Free Wi-Fi
R6 675+
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 R3 801. The highest prices are found on Saturday, with average rates at R11 247.
Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

March
July
R3 309
R3 058
Cheapest month to stay with an average 61% drop in price.
Most expensive month to stay with an average 264% 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 R971. 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 R870 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, agritourism, towers, homestays, luxury tents, campgrounds, barns, caravans, castles, chalets, condos, campsites, hotels, caravan parks, 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

Pistoia holiday rentals

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