Chianti holiday rentals

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

Here is why travelers 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.

Best Chianti holiday rentals

Most recommended holiday rentals in Chianti

Show all
Tenuta La Fratta - Sinalunga - Pool
Tenuta La Fratta
8.2 Very Good
AED 485+
AED 485+
Parking
Free Wi-Fi
Pool
Pet-friendly
Agriturismo Pratovalle - Sinalunga - Pool
Agriturismo Pratovalle
8.6 Very Good
AED 415+
AED 415+
Parking
Free Wi-Fi
Pool
Pet-friendly
Florence Villa Violetta - Bagno a Ripoli - Patio
Florence Villa Violetta - Bagno a Ripoli - Patio
Florence Villa Violetta
9.8 Wonderful
AED 769+
AED 769+
Parking
Free Wi-Fi
Air conditioning
Willy - Sweet Dreams in Florence - Bagno a Ripoli - Bedroom
Willy - Sweet Dreams in Florence - Bagno a Ripoli - Bedroom
Willy - Sweet Dreams in Florence
8.6 Very Good
AED 892+
AED 892+
Parking
Free Wi-Fi
Air conditioning
Borgo I Vicelli Adults Only Relais - Bagno a Ripoli - Bedroom
Borgo I Vicelli Adults Only Relais - Bagno a Ripoli - Bedroom
Borgo I Vicelli Adults Only Relais
9.1 Wonderful
AED 939+
AED 939+
Parking
Free Wi-Fi
Pool
Pet-friendly
Agriturismo Il Colle - Bagno a Ripoli
Agriturismo Il Colle - Bagno a Ripoli
Agriturismo Il Colle
9.1 Wonderful
AED 984+
AED 984+
Free Wi-Fi
Pet-friendly
Air conditioning
Palagio 8 in Chianti With Shared Pool - Rignano sull'Arno - Building
Palagio 8 in Chianti With Shared Pool - Rignano sull'Arno - Building
Palagio 8 in Chianti With Shared Pool
AED 1,219+
AED 1,219+
Free Wi-Fi
Holiday Home Poggio Cuccule by Interhome - Montevarchi - Living room
Holiday Home Poggio Cuccule by Interhome - Montevarchi - Living room
Holiday Home Poggio Cuccule by Interhome
10 Wonderful
AED 2,314+
AED 2,314+
Free Wi-Fi
Pool
Pet-friendly
Apartment-Superior-Ensuite - Rignano sull'Arno - Bedroom
Apartment-Superior-Ensuite - Rignano sull'Arno - Bedroom
Apartment-Superior-Ensuite
AED 639+
AED 639+
Free Wi-Fi
Air conditioning
Appartamento Piero - Bagno a Ripoli
Appartamento Piero - Bagno a Ripoli
Appartamento Piero
9.2 Wonderful
AED 522+
AED 522+
Parking
Free Wi-Fi
Pool
Air conditioning
Agriturismo Villa Le Vigne - Montevarchi
Agriturismo Villa Le Vigne - Montevarchi
Agriturismo Villa Le Vigne
8.8 Very Good
AED 420+
AED 420+
Parking
Free Wi-Fi
Pool
Pet-friendly
Agriturismo Podere Luisa - Montevarchi
Agriturismo Podere Luisa - Montevarchi
Agriturismo Podere Luisa
9.1 Wonderful
AED 327+
AED 327+
Parking
Free Wi-Fi
Pool
Pet-friendly
Il Palagetto - Bagno a Ripoli
Il Palagetto - Bagno a Ripoli
Il Palagetto
8.6 Very Good
AED 697+
AED 697+
Parking
Free Wi-Fi
Pool
Appartamento Giulio - Bagno a Ripoli
Appartamento Giulio - Bagno a Ripoli
Appartamento Giulio
9.3 Wonderful
AED 514+
AED 514+
Parking
Free Wi-Fi
Pool
Air conditioning
Casa Vacanze Ada - Fiesole
Casa Vacanze Ada - Fiesole
Casa Vacanze Ada
8.7 Very Good
AED 585+
AED 585+
Parking
Free Wi-Fi
Pool
Pet-friendly
Podere Zelmira - Sinalunga
Podere Zelmira - Sinalunga
Podere Zelmira
9.4 Wonderful
AED 786+
AED 786+
Parking
Free Wi-Fi
Pool
Pet-friendly
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

AED 0 - AED 2,196AED 2,196 - AED 4,393AED 4,393 - AED 6,589AED 6,589 - AED 8,785AED 8,785+ per night

Property type

ApartmentHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

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.

Which month has the cheapest vacation rental rates in Chianti?

Vacation rentals are cheapest in Chianti in January, with average rates of AED 1,154. In comparison, October is the most expensive month, with prices at AED 8,288.

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 AED 2,767. The highest prices are found on Friday, with average rates at AED 7,104.
Find deals

Good to know

Low season

March

High season

November

Average price (weeknight)

AED 611

Average price (weekend night)

AED 1,293
Cheapest month to stay with an average 33% drop in price.
Most expensive month to stay with an average 109% 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 AED 225. 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 agritourism, apartments, farm stays, villas, houses, homestays, towers, chalets, cottages, barns, campgrounds, caravans, caravan parks, castles, condos, campsites, luxury tents and lodges.

  • 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 Camping Village Il Poggetto.

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

    There are a number of dog and pet-friendly Chianti holiday rentals, with around 19% allowing you to bring your pet along with you.

See more FAQs

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

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