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Holiday apartments and houses in Chianti

Name: Holiday homes & apartments in Chianti
Brand: Ferienhausmiete
Rating: 4.3 (383 reviews)

39 offers for your holiday in Chianti

Gaiole in Chianti

Ancient tower with private pool 5+1

6 guests

120 m²

3 bedrooms

25 reviews

Ancient tower for 5 to 6 persons in a medieval castle near Siena in Chianti, panoramic views, 3 bedrooms, 2 bathrooms, garden, pool, air conditioning, fireplace, satellite TV, WIFI

from 200 € per night / night

4.9

prices from 200€ per night

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Poggibonsi

Holy Path

2 guests

25 m²

1 bedroom

Cammino Santo is located on the hills between Poggibonsi and San Gimignano, approximately halfway between Siena and Florence.

from 115 € per night / night

prices from 115€ per night

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Poggibonsi

Casalecchi

4 guests

70 m²

2 bedrooms

2 reviews

Romantic cottage in Tuscany in the middle of the Chianti Classico ideal for families & couples

from 122 € per night / night

5.0

prices from 122€ per night

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Castellina in Chianti

Il Girasole Casini

6 guests

110 m²

3 bedrooms

2 reviews

Charming holiday villa for 6 people with pool near Siena!

from 177 € per night / night

4.5

prices from 178€ per night

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Gaiole in Chianti

Gaiole 2 with private swimming lake

8 guests

115 m²

3 bedrooms

Free cancellation

Lovingly restored holiday home for 6-8 people with private swimming lake in former farmhouse, located in the heart of the Chianti Classico area!

Free cancellation

from 250 € per night / night

prices from 250€ per night

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Greve in Chianti

Chianti Villa Chicco

5 guests

102 m²

2 bedrooms

Free cancellation

Sustainable

Chianti Villa Chicco, private heated pool, large garden, BBQ, and parking

Free cancellation

Sustainable

from 231 € per night / night

prices from 231€ per night

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Holiday home relaxing holiday Gaiole in Chianti

Gaiole in Chianti

Holiday home relaxing holiday Gaiole in Chianti

6 guests

65 m²

2 bedrooms

This typical stone farm is located on the Chianti hills bewteen Siena (17 Km) and Gaiola in Chainti (12 Km).

from 205 € per night / night

prices from 205€ per night

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Radda in Chianti

Escape to Vineyards, Elba

4 guests

80 m²

2 bedrooms

21 reviews

Free cancellation

On the 1st floor: (Living room, open kitchen(TV(satellite), coffee machine, oven, dishwasher, fridge-freezer, terrace), bedroom(double bed), bedroom(double bed)

Free cancellation

from 63 € per night / night

4.4

prices from 63€ per night

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Casciano Val di Pesa

Belvilla by OYO La Romola

5 guests

80 m²

1 bedroom

1 review

Free cancellation

Ground floor: (Kitchen(hob, electric kettle, toaster, coffee machine, espresso machine, microwave, dishwasher, fridge, washing machine)

Free cancellation

Price on request

Radda in Chianti

Chianti Hillside Farmhouse

16 guests

270 m²

6 bedrooms

45 reviews

Free cancellation

Ground floor: (Living room, open kitchen(double sofa bed, TV(satellite), coffee machine, oven, dishwasher, fridge-freezer, terrace), bedroom(double bed)

Free cancellation

from 211 € per night / night

4.5

prices from 212€ per night

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Casciano Val di Pesa

Wine Tastings, Hills and Tuscan home

9 guests

150 m²

3 bedrooms

67 reviews

Free cancellation

Ground floor: (Living room(single sofa bed, high chair), open kitchen(dining table, cooker(4 ring stoves), oven(mini), microwave, fridge-freezer)

Free cancellation

from 115 € per night / night

4.4

prices from 116€ per night

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Greve in Chianti

Tuscan Charm in Greve

4 guests

100 m²

2 bedrooms

46 reviews

Free cancellation

Ground floor: (Living room(double sofa bed, TV(satellite), fireplace), Large kitchen(cooker(4 ring stoves), oven, microwave, dishwasher, fridge-freezer)

Free cancellation

from 136 € per night / night

4.2

prices from 137€ per night

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Holiday Home in Chianti with Pool & Terrace

Castelfranco di Sopra

Holiday Home in Chianti with Pool & Terrace

2 guests

45 m²

1 bedroom

10 reviews

Free cancellation

On the 1st floor: (Large kitchen(TV(international television channels, no dutch television channels), TV, dining table, hob, electric kettle, toaster, cooker, hood, fridge-freezer)

Free cancellation

from 75 € per night / night

4.2

prices from 75€ per night

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Castelfranco di Sopra

Holiday Home in Chianti with Pool and Views

4 guests

75 m²

2 bedrooms

13 reviews

Free cancellation

Ground floor: (Large kitchen(TV(international television channels, no dutch television channels), dining table, hob, electric kettle, toaster, cooker, hood, fridge-freezer)

Free cancellation

from 102 € per night / night

4.2

prices from 103€ per night

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Casciano Val di Pesa

Tuscany Bliss: Garden Retreat

5 guests

170 m²

3 bedrooms

37 reviews

Free cancellation

Ground floor: (Large kitchen(dining table, hob, electric kettle, boiling water tap, cooker, hood, coffee machine, oven, microwave, dishwasher, fridge-freezer)

Free cancellation

from 98 € per night / night

4.4

prices from 99€ per night

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Castelfranco Piandiscò

Villa in Pian di Sco with swimming pool

8 guests

250 m²

4 bedrooms

Free cancellation

Living room(TV, air conditioning), Kitchen(stove, electric kettle, toaster, coffee machine, oven, microwave, dishwasher, fridge, freezer, Food processor)

Free cancellation

from 454 € per night / night

prices from 455€ per night

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Castelfranco Piandiscò

Hillside Retreat with a View

5 guests

80 m²

3 bedrooms

48 reviews

Free cancellation

Ground floor: (Living room(dining table, fireplace, seating area), open kitchen(stove, hob(gas), electric kettle, cooker, espresso machine, oven, fridge-freezer)

Free cancellation

from 118 € per night / night

4.0

prices from 119€ per night

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Cavriglia

Serene Chianti Retreat

4 guests

90 m²

2 bedrooms

30 reviews

Free cancellation

Ground floor: (Living room(fireplace), Kitchen, bedroom(double bed), bedroom(double bed), bathroom(shower, washbasin, toilet), bathroom(shower, washbasin, toilet))

Free cancellation

from 103 € per night / night

4.3

prices from 103€ per night

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Castelfranco Piandiscò

Villa in Pian di Sco with swimming pool

8 guests

190 m²

4 bedrooms

Free cancellation

Living room(TV, fireplace), Kitchen(stove, electric kettle, toaster, coffee machine, oven, microwave, dishwasher, fridge, freezer, Food processor)

Free cancellation

from 416 € per night / night

prices from 416€ per night

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Castelfranco di Sopra

Villa in Tuscany with Pool near Beach

2 guests

50 m²

1 bedroom

20 reviews

Free cancellation

Ground floor: (Large kitchen(dining table, hob(4 ring stoves), electric kettle, toaster, cooker, hood, espresso machine, fridge-freezer)

Free cancellation

from 77 € per night / night

4.2

prices from 77€ per night

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Casciano Val di Pesa

Holiday Home in Tuscany with Vineyards

3 guests

45 m²

1 bedroom

35 reviews

Free cancellation

Ground floor: (terrace(shared with other guests), garden, garden furniture, BBQ, parking, swimming pool(shared with other guests, 10 x 5 m.

Free cancellation

from 65 € per night / night

4.4

prices from 66€ per night

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Casciano Val di Pesa

Cottage in Tuscany with Pool & BBQ

4 guests

65 m²

2 bedrooms

17 reviews

Free cancellation

Ground floor: (open kitchen(cooker(4 ring stoves, gas), microwave, fridge-freezer), Living/diningroom(dining table, high chair), bedroom(double bed, children's bed)

Free cancellation

from 74 € per night / night

4.6

prices from 75€ per night

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Radda in Chianti

Apartment in Radda with Garden

6 guests

60 m²

2 bedrooms

19 reviews

Free cancellation

Ground floor: (bedroom(double bed), bathroom(shower, washbasin, toilet, bidet)) On the 1st floor: (Living room(TV(satellite))

Free cancellation

from 58 € per night / night

4.3

prices from 59€ per night

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Cavriglia

Tranquil Chianti Escape for 4

4 guests

90 m²

2 bedrooms

10 reviews

Free cancellation

On the 1st floor: (Living room(fireplace), Kitchen(hob, coffee machine, oven, fridge), bedroom(double bed), bedroom(double bed), bathroom(shower, washbasin, toilet)

Free cancellation

from 102 € per night / night

4.3

prices from 103€ per night

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Apartment Tuscany near Pratomagno Mountain

Castelfranco Piandiscò

Apartment Tuscany near Pratomagno Mountain

6 guests

160 m²

3 bedrooms

21 reviews

Free cancellation

On the 1st floor: (Living room(dining table, fireplace, seating area), Kitchen(dining table, hob, cooker, hood, espresso machine, oven, dishwasher, fridge-freezer)

Free cancellation

from 109 € per night / night

4.1

prices from 109€ per night

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Guest reviews of our holiday apartments in Chianti

August 2018

Nadine K. from 10713 Berlin

5.0

Verified guest from Tourist-paradise.com

Casalecchi

Poggibonsi

View German

Beautiful holiday home

It was just great here. The house was very nicely furnished. We wanted for nothing. A beautiful view of the valley. Everyone was very friendly. We had an unforgettable holiday.

from 122€ night

June 2026

4.4

Tuscany Bliss: Garden Retreat

Casciano Val di Pesa

View German

Everything was as described, and we had no problems during our stay. The WiFi was strong, which helped us balance work and relaxation. A practical choice for remote workers!

from 99€ night

June 2026

4.6

Cottage in Tuscany with Pool & BBQ

Casciano Val di Pesa

View German

Definitely recommended if you want to explore Tuscany without breaking the budget. It has charm and convenience, so I enjoyed every moment here while exploring nearby towns such as San Gimignano and Siena.

from 75€ night

More inspiration for your vacation planning

Vacation ideas in Chianti

Dog friendly holidays in Chianti

holiday homes with pool in Chianti

holiday in the mountains in Chianti

Are you still looking for the right holidaymakers for your holiday home or apartment?

You are still looking for the right holidaymakers

for your holiday home or apartment?

Rent out now on Ferienhausmiete.de

When do you want to travel?

Best travel time for the region Chianti

Our price and availability stats help you find the best time to travel.

Cheapest month:

April - Ø 156€/night

Most expensive month:

July - Ø 246€/night

Best chances for available stays:

October - 57% available

Lowest availability:

May - only 40% available

Holiday home prices in Chianti

198€ for 13 Jun - 20 Jun

190€ Yearly average

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Average price per night in €

Holiday home availability in Chianti

57% for 13 Jun - 20 Jun

47% Yearly average

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Available accommodations in %

Holiday Advisor

Good to know for vacationers

sights

activities with children

food & beverages

art & culture

arrival

Which sights are there in Chianti?

Out of the Casa, into the Castello!

The municipality of Gaiole has come up with something to make it easier for visitors to reach the most beautiful castles, buildings, villages, and sights: "the road of the castles". There are a total of six different routes where you can experience both the history and architecture of Tuscany. Highlights along the routes include the Castello di Brolio with its beautiful Renaissance gardens near Siena and the Castello di Verrazzano, a historic winery. The hilltop castle has a centuries-old wine cellar. Other destinations that combine wine enjoyment and history are Castelnuovo Berardenga in the province of Siena, a former surveillance castle on the border with Arezzo and Florence, and Castello di Montefioralle. It is considered the oldest village in Chianti and has an ancient city wall. Also worth seeing is the Castello di Volpaia winery near Greve. From your holiday apartment or holiday home with a pool, day trips to the cultural and historical cities of San Gimignano, Florence, Siena, and the surrounding area are also possible. Discover the past of the Chianti region. Among the first settlers here were the powerful Etruscans. Many of their artifacts have been excavated around Castellina.

What can you experience in Chianti with children?

Family vacation in an exclusive villa with pool and garden

Whether near San Gimignano, Castellina, Greve, Panzano, or Castelnuovo Berardenga - you will find spacious, affordable villas and houses in quiet locations throughout the Chianti province. Many of them have a private pool and garden. This is appreciated not only by those seeking relaxation but especially by families traveling with children or a pet. The equipment of most accommodations is child-friendly. In many holiday apartments and holiday homes, pets are also allowed. So, a relaxed holiday with a dog in Chianti is no problem. Italy is considered a very child-friendly country. Nobody looks strange here when the children play a little louder and romp around wildly. The dog will particularly enjoy forays through the surrounding hills. For children, on the other hand, a Tuscan farm, such as the one in Panzano, is a real experience. And if the longing for the sea is too great:

Where can I eat out in Chianti?

In Italy, people say "Alla salute!" and "Buon appetito!"

If you have already been on holiday in other regions and beautiful provinces of the country, such as Abruzzo, Basilicata, Trentino-South Tyrol, or Piedmont, you know how diverse and delicious Italian cuisine can be. This is no different in Tuscany. In addition to the well-known pizza and pasta dishes, you can look forward to some special delicacies, such as the wonderful red wine. In the hills between Siena and the surroundings of Florence, excellent bruschetta, the spicy pork sausage "Finocchiata," and "crostini," toasted bread slices spread with chicken liver, are served. Of course, this is accompanied by a young or aged Chianti Classico wine. A particularly noble drop comes from the famous Panzano. As well known as the place is for its good wines, the Maremma landscape in southern Tuscany is famous for its delicious cheese. And it is well known that cheese tastes particularly good with grape juice! It is best to always have a bottle of red wine ready in your holiday apartment or holiday home, for example in Radda, to enjoy it in the garden of your accommodation. Taste the enchanting delicacies and don't miss the wine tastings. Give your heart to the delicious grape here.

What is a must-see in Chianti?

Chianti: Rich not only in wine but also in culture

The cultural landscape of Tuscany is known worldwide. Whether painting, music, sculpture, or architecture - in every corner, you will find witnesses of the past and heirs of centuries-old traditions and history. Numerous museums that will lure you out of the pool of your holiday apartment or holiday home speak for this. Sacred art can be found, for example, in the museum in Tavarnelle Val di Pesa. In contrast, you can learn everything about rural culture and the old professions of the idyllic Chianti region in the Tuscan crafts museum in San Donato in Poggio. The Archaeological Museum in Castellina is also a visitor magnet. The museum's equipment includes a sandstone big cat head. Exhibitions on religious art from the region can be found in San Casciano in Val di Pesa. Immerse yourself in the pool and fascinating culture!

How do I come to Chianti?

Your journey to the Tuscan region of Chianti in Italy

The Chianti hills in Tuscany stretch from Pisa to Montalcino. Officially, there are nine sub-regions. The two most important are those around Florence and Siena. However, regardless of whether you rent a holiday apartment or a holiday home in Val di Pesa, Castellina, Gaiole or Greve - the magic of Chianti, picturesque wine villages and an unforgettable holiday are guaranteed. Tuscany is located in central Italy and borders the regions of Lazio, Umbria, Marche, Liguria, and Emilia-Romagna. The airports in Florence and Pisa are relevant for a flight to the Chianti area. They are directly served by many German cities, including numerous low-cost airlines. Once you have your feet back on the ground, a rental car is recommended. This way, you can drive right up to your private holiday accommodation. Your own vehicle will also be useful when exploring the region. And there is a lot to discover - apart from the pool of your private villa or estate. Nothing stands in the way of your dream vacation. Spend wonderful days or weeks here.

Information about holiday homes & apartments in Chianti

Helpful Information

Available vacation rentals

39 offers

Possible discounts

up to 35%

Min. price per night

from 50 €

Popular amenities

dog friendly vacation, TV, Wifi, garden and swimming pool

Pets allowed

26 offers

Accommodations with pool

36 offers

Frequently asked questions

FAQs

How much does a holiday accommodation cost in Chianti?

From 50 € you can book our accommodations in Chianti and stay in an average of 120 m² (holiday houses) and 70 m² (apartments).

Where is the cheapest holiday in Chianti?

We have many attractive offers for vacation apartments and holiday homes in Greve in Chianti or Radda in Chianti. If you spend your vacation here, you can rent a beautiful accommodation from 50 € per night.

Which are the best holiday apartments and houses in Chianti?

For a successful stay in Chianti, we recommend the vacation accommodations Il Girasole Casini, Ancient tower with private pool 5+1 and Casalecchi.

Are there dog-friendly holiday apartments in Chianti?

You don't have to leave your pet behind in Chianti, as there are 26 accommodations that allow pets. Dog owners feel particularly comfortable in Castelfranco di Sopra, Radda in Chianti and Castelfranco Piandiscò.

Where is the best place to book a holiday in Chianti?

At Ferienhausmiete.de you will find the best vacation apartments & holiday homes at the lowest price. Book directly with the landlord and save on additional fees.

Holiday apartments and houses in Chianti

39 offers for your holiday in Chianti

Guest reviews of our holiday apartments in Chianti

Beautiful holiday home

More inspiration for your vacation planning

Vacation ideas in Chianti

When do you want to travel?

Best travel time for the region Chianti

Holiday home prices in Chianti

Average price per night in €

Holiday home availability in Chianti

Available accommodations in %

Holiday Advisor

Good to know for vacationers

Which sights are there in Chianti?

Out of the Casa, into the Castello!

What can you experience in Chianti with children?

Family vacation in an exclusive villa with pool and garden

Where can I eat out in Chianti?

In Italy, people say "Alla salute!" and "Buon appetito!"

What is a must-see in Chianti?

Chianti: Rich not only in wine but also in culture

How do I come to Chianti?

Your journey to the Tuscan region of Chianti in Italy

Information about holiday homes & apartments in Chianti

Helpful Information

Frequently asked questions

FAQs

How much does a holiday accommodation cost in Chianti?

Where is the cheapest holiday in Chianti?

Which are the best holiday apartments and houses in Chianti?

Are there dog-friendly holiday apartments in Chianti?

Where is the best place to book a holiday in Chianti?

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