Chianti vacation rentals

Search hundreds of travel sites at once for car rental 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.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from C$ 118

Best Chianti vacation rentals

Mastrojanni Relais - Montalcino - Restaurant
Mastrojanni Relais
Montalcino, TO, Italy
9.7Wonderful(330)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 787+
Check availability
Porta nuova home - Colle di Val d'Elsa - Living room
Porta nuova home
Colle di Val d'Elsa, TO, Italy
9.1Wonderful(97)
Apartment
Free Wi-Fi
C$ 189+
Check availability
Azienda Agraria La Casella - Montalcino - Living room
Azienda Agraria La Casella
Montalcino, TO, Italy
9.0Wonderful(715)
Farm stay
Parking
Free Wi-Fi
Pet friendly
C$ 216+
Check availability
hu Firenze Camping in Town - Florence - Bedroom
hu Firenze Camping in Town
Campo di Marte
8.6Very good(14708)
Campground
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 85+
Check availability
La Terrazza Cortonese - Cortona - Bedroom
La Terrazza Cortonese
Cortona, TO, Italy
9.7Wonderful(4)
Apartment
Free Wi-Fi
C$ 390+
Check availability
Gli Archi nel Cuore di Siena - Siena
Gli Archi nel Cuore di Siena
Siena, TO, Italy
8.7Very good(28)
Apartment
Free Wi-Fi
C$ 260+
Check availability
Wave House - Siena
Wave House
Siena, TO, Italy
8.3Very good(16)
Apartment
Free Wi-Fi
C$ 240+
Check availability
agriturismo l'arte dei semplici - Montalcino
agriturismo l'arte dei semplici
Montalcino, TO, Italy
8.6Very good(222)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 141+
Check availability
Fattoria Di Mugnano - Colle di Val d'Elsa
Fattoria Di Mugnano
Colle di Val d'Elsa, TO, Italy
9.1Wonderful(297)
Farm stay
Parking
Free Wi-Fi
Pet friendly
C$ 163+
Check availability
Poggio Martino - Cortona
Poggio Martino
Cortona, TO, Italy
9.4Wonderful(65)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 194+
Check availability
Bv Apartment Siena - Siena
Bv Apartment Siena
Siena, TO, Italy
9.0Wonderful(115)
Apartment
Free Wi-Fi
Pet friendly
C$ 144+
Check availability
Nobil Dimora Ancilli - Siena
Nobil Dimora Ancilli
Siena, TO, Italy
8.3Very good(44)
Apartment
Free Wi-Fi
Pet friendly
C$ 600+
Check availability
Agriturismo Il Torrino - Cortona
Agriturismo Il Torrino
Cortona, TO, Italy
9.4Wonderful(11)
Farm stay
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 374+
Check availability
Dietro Le Mura - Colle di Val d'Elsa
Dietro Le Mura
Colle di Val d'Elsa, TO, Italy
9.6Wonderful(210)
Apartment
Parking
Free Wi-Fi
Pet friendly
C$ 199+
Check availability
Castel Brunello - Montalcino
Castel Brunello
Montalcino, TO, Italy
9.7Wonderful(910)
Apartment
Parking
Free Wi-Fi
Pool
C$ 638+
Check availability
Agriturismo Villa Paradisino Musico - Montalcino
Agriturismo Villa Paradisino Musico
Montalcino, TO, Italy
8.9Very good(24)
Farm stay
Parking
Free Wi-Fi
Pool
C$ 309+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
August
C$ 211
C$ 219
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 15% 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 vacation home in Chianti

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

    In the last 72 hours, users have found Chianti vacation rentals for tonight for as low as C$ 61. Search here for similar prices

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

    In the last 72 hours, users have found Chianti vacation rentals for this weekend for as low as C$ 55 per night. Search here for similar prices

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

    The average price for a weekly Chianti vacation rental found by KAYAK users in the last 2 weeks is C$ 1,612.

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

    The average price for a monthly Chianti vacation rental found by KAYAK users in the last 2 weeks is C$ 6,907.

  • What types of vacation rentals are available in Chianti?

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

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

    There are many types of properties available for Chianti vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are hu Firenze Camping in Town and Camping Village Il Poggetto.

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

    There are a number of dog and pet-friendly Chianti vacation rentals, with around 14% 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 vacation home.

Everything you need to know for your stay in Chianti