Chianti vacation rentals

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Latest Chianti vacation rental deals

MOST POPULARFlorence
Vacation homes from $36
San Gimignano
Vacation homes from $134
Montalcino
Vacation homes from $332

Best Chianti vacation rentals

Most recommended vacation rentals in Chianti

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Borgo I Vicelli Adults Only Relais - Bagno a Ripoli - Bedroom
Borgo I Vicelli Adults Only Relais
Bagno a Ripoli, TO, Italy
9.2Wonderful(670)
Parking
Free Wi-Fi
Pool
Pet friendly
$259+
Check availability
Willy - Sweet Dreams in Florence - Bagno a Ripoli - Bedroom
Willy - Sweet Dreams in Florence
Bagno a Ripoli, TO, Italy
8.7Very good(17)
Parking
Free Wi-Fi
$232+
Check availability
Casa Ruffino - Wine Relais - Bagno a Ripoli - Bedroom
Casa Ruffino - Wine Relais
Bagno a Ripoli, TO, Italy
9.0Wonderful(221)
Parking
Free Wi-Fi
Pool
Pet friendly
$311+
Check availability
Florence Villa Violetta - Bagno a Ripoli - Patio
Florence Villa Violetta
Bagno a Ripoli, TO, Italy
9.9Wonderful(37)
Parking
Free Wi-Fi
$234+
Check availability
Camping Village Panoramico Fiesole - Fiesole - Balcony
Camping Village Panoramico Fiesole
Fiesole, TO, Italy
8.5Very good(1407)
Parking
Free Wi-Fi
Pool
Pet friendly
$131+
Check availability
Le Ragnaie - Montalcino - Pool
Le Ragnaie
Montalcino, TO, Italy
9.0Wonderful(993)
Parking
Free Wi-Fi
Pool
Pet friendly
$294+
Check availability
Borgo dei Rosai - Bagno a Ripoli
Borgo dei Rosai
Bagno a Ripoli, TO, Italy
9.8Wonderful(5)
Parking
Free Wi-Fi
Pet friendly
$198+
Check availability
La Casa in Toscana - Cortona
La Casa in Toscana
Cortona, TO, Italy
8.4Very good(20)
Parking
Free Wi-Fi
$212+
Check availability
Il Palagetto - Bagno a Ripoli
Il Palagetto
Bagno a Ripoli, TO, Italy
8.4Very good(209)
Parking
Free Wi-Fi
Pool
$199+
Check availability
Appartamento La Casina - Pistoia
Appartamento La Casina
Pistoia, TO, Italy
9.4Wonderful(204)
Parking
Free Wi-Fi
Pet friendly
$138+
Check availability
Coco Places Firenze, Centro Storico - Florence
Coco Places Firenze, Centro Storico
Centro Storico
9.0Wonderful(1203)
Free Wi-Fi
$407+
Check availability
Appartamento Isabella - Pistoia
Appartamento Isabella
Pistoia, TO, Italy
8.6Very good(165)
Free Wi-Fi
Pet friendly
$87+
Check availability
Appartamento Santa Croce - Arezzo
Appartamento Santa Croce
Arezzo, TO, Italy
9.3Wonderful(56)
Free Wi-Fi
$177+
Check availability
Magnolia - Mercatale Val Di Pesa
Magnolia
Mercatale Val Di Pesa, TO, Italy
8.5Very good(3)
Parking
Free Wi-Fi
Pool
$180+
Check availability
Vasari Home - Arezzo
Vasari Home
Arezzo, TO, Italy
8.6Very good(67)
Free Wi-Fi
Pet friendly
$127+
Check availability
Appartamento i Fabbri - Pistoia
Appartamento i Fabbri
Pistoia, TO, Italy
9.1Wonderful(101)
Free Wi-Fi
Pet friendly
$125+
Check availability
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$0 - $280$280 - $559$559 - $838$838 - $1,117$1,117+ per night

Property Types

ApartmentHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

March

High season

November

Average price (weeknight)

$208

Average price (weekend night)

$510
Cheapest month to stay with an average 45% drop in price.
Most expensive month to stay with an average 67% 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 $70. 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 $1,272.

  • 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 $5,450.

  • 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 apartments, farm stays, houses, villas, agritourism, barns, campgrounds, caravans, caravan parks, castles, chalets, condos, cottages, holiday parks, homestays, luxury tents, towers 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 Lupaia and hu Firenze Camping in Town.

  • What are the most popular Chianti vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Opera 19 Luxury Apartment and Casetta Tartuchino.

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

    There are a number of dog and pet-friendly Chianti vacation rentals, with around 18% allowing you to bring your pet along with you.

See more FAQs

Where to stay in Chianti?

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Everything you need to know for your stay in Chianti

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Vacations in Chianti

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