Chianti Region holiday rentals

We found 8,317 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Chianti Region

Showing deals for:11 Dec - 18 Dec

Living area
Pool
Outdoor dining
Private kitchen
Exceptional
(6 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

8% off
AU$11,588
for 7 nights, 1 villa
AU$1,655 per night
includes taxes & fees
Private villa in the heart of chianti with view of siena
Enterance
Living area
Room
Living area
Exceptional
(16 reviews)

Steps to Ponte Vecchio.3BR/3BA+terrace w view of Pitti Palace

Florence

8% off
AU$5,010
for 7 nights, 1 apartment
AU$716 per night
includes taxes & fees
Steps to Ponte Vecchio.3BR/3BA+terrace w view of Pitti Palace
The kitchen in the dining room
The courtyard of the building
Second double bedroom
The dining room
Exceptional
(185 reviews)

Charming 3 bedroom Brand New Apartment in a Historic Building.

Florence

9% off
AU$3,367
for 7 nights, 1 apartment
AU$481 per night
includes taxes & fees
Charming 3 bedroom Brand New Apartment in a Historic Building.
The Cathedral with his Giotto's bell tower
Room
Door way
Living room with sofa bed
Exceptional
(147 reviews)

SMART APT CLOSE TO PITTI PALACE IN THE OLD CENTER OF OLTRARNO

Florence

8% off
AU$1,821
for 7 nights, 1 apartment
AU$260 per night
includes taxes & fees
SMART APT CLOSE TO PITTI PALACE IN THE OLD CENTER OF OLTRARNO
Dining
Shared bbq area
Private outside area
Private garden and swimming pool
Exceptional
(38 reviews)

Villa in the Heart of Chianti

Greve in Chianti

14% off
AU$6,378
for 7 nights, 1 villa
AU$911 per night
includes taxes & fees
Villa in the Heart of Chianti
Living room
Dining room
Room
Kitchen
Exceptional
(196 reviews)

Apartment/ flat - Firenze

Florence

8% off
AU$1,473
for 7 nights, 1 apartment
AU$210 per night
includes taxes & fees
Apartment/ flat - Firenze
Interior
Living area
Living area
Interior
Exceptional
(34 reviews)

Apartment overlooking the Duomo

Florence

13% off
AU$2,196
for 7 nights, 1 apartment
AU$314 per night
includes taxes & fees
Apartment overlooking the Duomo
Outdoor dining
Property grounds
Pool
Interior
Exceptional
(16 reviews)

Luxury Suite in Renaissance Villa

Bagno a Ripoli

5% off
AU$1,855
for 7 nights, 1 room
AU$265 per night
includes taxes & fees
Luxury Suite in Renaissance Villa
Kitchen
Property grounds
Interior
That indicated is the apartment
Exceptional
(112 reviews)

Beautiful and large apartment in great location, overlooking Ponte Vecchio

Florence

9% off
AU$4,174
for 7 nights, 1 apartment
AU$596 per night
includes taxes & fees
Beautiful and large apartment in great location, overlooking Ponte Vecchio
Dining
Outdoor dining
Property grounds
Pool
Exceptional
(113 reviews)

Exclusive Estate | Personal Concierge & Heated Pool

Impruneta

9% off
AU$14,145
for 7 nights, 1 villa
AU$2,021 per night
includes taxes & fees
Exclusive Estate | Personal Concierge & Heated Pool
Dining
Pool
Exterior
Property grounds
Exceptional
(9 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE

San Casciano in Val di Pesa

7% off
AU$1,657
for 7 nights, 1 apartment
AU$237 per night
includes taxes & fees
RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE
Exterior
Property grounds
Property grounds
Interior
Exceptional
(8 reviews)

The Bartaline hut

Greve in Chianti

9% off
AU$1,445
for 7 nights, 1 home
AU$206 per night
includes taxes & fees
The Bartaline hut
Pool
Property grounds
Living area
Interior
Exceptional
(82 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
AU$896
for 7 nights, 1 home
AU$128 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Property grounds
Interior
Interior
Room
Exceptional
(33 reviews)

CasaGiardinoUno Simply Florence

Florence

13% off
AU$3,240
for 7 nights, 1 apartment
AU$463 per night
includes taxes & fees
CasaGiardinoUno Simply Florence
Living area
Property grounds
Terrace/patio
Exterior
Exceptional
(5 reviews)

7km Florence, garden, terrace & relax!

San Casciano in Val di Pesa

9% off
AU$878
for 7 nights, 1 apartment
AU$125 per night
includes taxes & fees
7km Florence, garden, terrace & relax!
Property grounds
Pool
Property grounds
Private kitchen
Exceptional
(28 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!

San Casciano in Val di Pesa

8% off
AU$1,491
for 7 nights, 1 apartment
AU$213 per night
includes taxes & fees
RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!
Living area
Terrace/patio
Interior
Property grounds
Exceptional
(5 reviews)

Le Piccole Scalette"Under the Tuscan Sun"

Scandicci

9% off
AU$2,764
for 7 nights, 1 apartment
AU$395 per night
includes taxes & fees
Le Piccole Scalette"Under the Tuscan Sun"
Room
Interior
Living area
Private kitchen
Exceptional
(69 reviews)

Bardi Apartment, Stunning View Of Ponte Vecchio!

Florence

9% off
AU$4,030
for 7 nights, 1 apartment
AU$576 per night
includes taxes & fees
Bardi Apartment, Stunning View Of Ponte Vecchio!
Interior
Exterior
Interior
Dining
Exceptional
(110 reviews)

BRIGHT LOFT IN THE HEART OF FLORENCE A FEW STEPS FROM UFFIZZI

Florence

8% off
AU$1,581
for 7 nights, 1 apartment
AU$226 per night
includes taxes & fees
BRIGHT LOFT IN THE HEART OF FLORENCE A FEW STEPS FROM UFFIZZI
Interior
Outdoor dining
Dining
Interior
Exceptional
(63 reviews)

Spacious and charming apartment in the heart of Florence

Florence

8% off
AU$3,338
for 7 nights, 1 apartment
AU$477 per night
includes taxes & fees
Spacious and charming apartment in the heart of Florence
Living 1 - fully furnished kitchen
Build entrance
Living n.1 - king size sofa bed.
Bedroom n.2: two single beds/king size bed (separated or united with king linen)
Exceptional
(93 reviews)

X-Large and luxury apartment in the old town! - All comfort -

Florence

9% off
AU$9,346
for 7 nights, 1 apartment
AU$1,335 per night
includes taxes & fees
X-Large and luxury apartment in the old town! - All comfort -
Dining
Outdoor dining
Private kitchen
Interior
Exceptional
(58 reviews)

Located in the most chic area of Florence, trendy clubs near Ponte Vecchio

Florence

18% off
AU$2,581
for 7 nights, 1 apartment
AU$369 per night
includes taxes & fees
Located in the most chic area of Florence, trendy clubs near Ponte Vecchio
COURTYARD 1350 AC
A CELLAR in CHIANTI
LEONARDO
A day in Tuscan Countryside...
Exceptional
(184 reviews)

Apartment in a 13th Century palace in the heart of Florence

Florence

7% off
AU$3,115
for 7 nights, 1 apartment
AU$445 per night
includes taxes & fees
Apartment in a 13th Century palace in the heart of Florence
The desk can also be a dining table
Elevators in front of the entrance door
Christmas in the Cathedral square just at the end of Via Ricasoli
Via Ricasoli
Exceptional
(142 reviews)

Just a few minutes from the Cathedral and the most beautiful Monuments in town

Florence

8% off
AU$909
for 7 nights, 1 apartment
AU$130 per night
includes taxes & fees
Just a few minutes from the Cathedral and the most beautiful Monuments in town
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Rustic Chianti Region will entice you

Enjoy the wineries and other features of Chianti Region. This relaxing and scenic city is well known for its local tours, sightseeing and restaurants. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Chianti Region

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chianti Region a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Borgo di Vescine - Tenute di Castelvecchi (1.4 mi / 2.3 km)
  • Castello di Albola (2.2 mi / 3.5 km)
  • Castello di Radda Winery (2.6 mi / 4.2 km)
  • Il Molino di Grace Winery (3.1 mi / 4.9 km)
  • Buondonno Winery (4.6 mi / 7.4 km)
  • Badia a Coltibuono (5.1 mi / 8.2 km)

Exploring the natural landscape of Chianti Region

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Chianti Region is a great place to get out in nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Alta Val d'Elsa River Park (15.4 mi / 24.7 km)
  • Boboli Gardens (16.8 mi / 27 km)
  • Arno River (16.8 mi / 27.1 km)
  • Cascine Park (19.2 mi / 30.9 km)
  • Terme Antica Querciolaia (20.6 mi / 33.2 km)
  • Olmo (21.8 mi / 35.1 km)

Travelling to and around Chianti Region

If you prefer to travel by train, Figline Valdarno Station, San Giovanni Valdarno Station and Incisa Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Chianti Region when booking a holiday home?
If you're headed for Chianti Region, Val dElsa is among the most sought-after locations to book a holiday property. While you're here, discover leading attractions like Collegiate Church of Santa Maria Assunta and Tenuta Torciano Winery.
What is the most popular type of holiday home accommodation in Chianti Region?
Apartments are the most popular kind of holiday home in Chianti Region, according to our data. Even if you have something different in mind, Stayz has holiday homes in many shapes and sizes. Compare our options to find your ideal fit.
How much does it cost to rent a holiday home in Chianti Region?
A number of factors affect how much you'll pay for a holiday home in Chianti Region, like the season, type of property and length of stay. Still, all of our holiday homes have something in common — incredible value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Chianti Region?
When you travel and the size and style of the property will influence the cost of your beachside escape. Enter your Chianti Region travel dates to view your options on Stayz. Can't live without a hot tub? Use our filters to choose the amenities and features you want.
What are popular home amenities in Chianti Region?
Some of the most popular home amenities people prefer in Chianti Region are off-street parking options, a garden and a washing machine. Whether you're travelling with family, your besties or even pets, Stayz holiday properties include the best amenities for hanging out with your loved ones.
Are there large group holiday homes in Chianti Region?
Chianti Region has 273 holiday homes that can host 10 or more guests. These properties come with enough space to share good times with your nearest and dearest.
What are the top attractions for families in Chianti Region?
There are loads of fabulous things to see and do with the family in Chianti Region, including:
  • Castellina Fortress
  • The Mall Luxury Outlet
  • Praetorian Palace
Can I find two-bedroom holiday homes in Chianti Region?
You can select from 421 two-bedroom properties in Chianti Region. Give your little ones the second room or fill it with a couple of your best friends. There's ample space for whoever's lucky enough to be coming along.
Are there holiday homes with WiFi in Chianti Region?
You can choose from 463 holiday homes with WiFi in Chianti Region. If you'd like to disconnect from the world on your trip, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Chianti Region?
The minimum required age is typically 16, 18 or 21. It can differ from property to property on Stayz, so look at the rules of your preferred Chianti Region holiday home before making a booking.
How long can I rent a holiday home in Chianti Region for?
How long you can rent a holiday home in Chianti Region varies according to the property. Simply enter your selected dates to display a list of options offering extended stays. With loads of features such as washing machines and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get someplace just right to call your home away from home in Chianti Region.

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