Sort by

Open map view

map

Sort by: Random

Holiday apartments and houses in Chianti

Name: Holiday homes & apartments in Chianti
Brand: Ferienhausmiete
Rating: 4.4 (435 reviews)

38 offers for your holiday in Chianti

Gaiole in Chianti

Burg Chianti

4 guests

70 m²

2 bedrooms

5% Last-Minute 09/07/2026 - 09/14/2026

Chianti Castle in Gaiole: 70 m², 2 rooms, space for 4 guests – experience history up close!

5% Last-Minute 09/07/2026 - 09/14/2026

from 232 € per night / night

prices from 232€ per night

View

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

View

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

View

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 118 € per night / night

5.0

prices from 118€ per night

View

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

View

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

View

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

View

Castelfranco Piandiscò

Holiday apartment with 2 bedrooms

6 guests

75 m²

2 bedrooms

Free cancellation

from 89 € per night / night

prices from 89€ per night

View

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 94 € per night / night

4.4

prices from 94€ per night

View

Castelfranco di Sopra

Holiday Home in Chianti with Pool and Views

4 guests

75 m²

2 bedrooms

32 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 100 € per night / night

4.3

prices from 100€ per night

View

Casciano Val di Pesa

Holiday Home with Vineyard Vibes

3 guests

58 m²

1 bedroom

40 reviews

Free cancellation

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

Free cancellation

from 64 € per night / night

4.4

prices from 65€ per night

View

Casciano Val di Pesa

Wine Tastings, Hills and Tuscan home

9 guests

150 m²

3 bedrooms

115 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 107 € per night / night

4.4

prices from 107€ per night

View

Farmhouse in Chianti with Pool and Garden

Cavriglia

Farmhouse in Chianti with Pool and Garden

8 guests

180 m²

4 bedrooms

36 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 194 € per night / night

4.3

prices from 195€ per night

View

Castelfranco Piandiscò

Belvilla by OYO Podere Campiglia

18 guests

330 m²

8 bedrooms

21 reviews

Free cancellation

Ground floor: (Living room(double sofa bed, TV, fireplace), Living room(TV, fireplace, seating area), dining room(dining table)

Free cancellation

from 526 € per night / night

4.7

prices from 527€ per night

View

Greve in Chianti

Chianti Romantic Retreat

2 guests

54 m²

1 bedroom

81 reviews

Free cancellation

On the 1st floor: (hallway(acces via outside stairway), open kitchen(cooker(4 ring stoves, electric), oven, fridge-freezer), Living/diningroom(double sofa bed, TV(satellite)

Free cancellation

from 25 € per night / night

4.1

prices from 26€ per night

View

Radda in Chianti

Pretty farmhouse with terrace

6 guests

80 m²

2 bedrooms

45 reviews

Free cancellation

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

Free cancellation

from 61 € per night / night

4.4

prices from 61€ per night

View

Casciano Val di Pesa

Tuscan Haven with Pool

3 guests

40 m²

1 bedroom

52 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 64 € per night / night

4.3

prices from 65€ per night

View

Castelfranco di Sopra

Holiday Home in Chianti with Pool

4 guests

55 m²

2 bedrooms

36 reviews

Free cancellation

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

Free cancellation

from 89 € per night / night

4.3

prices from 90€ per night

View

Belvilla by OYO Cottage in PiandiscÃ² with...

Castelfranco Piandiscò

Belvilla by OYO Cottage in PiandiscÃ² with...

5 guests

85 m²

3 bedrooms

15 reviews

Free cancellation

Ground floor: (Living room(TV, fireplace), dining room, open kitchen(oven, fridge-freezer), bedroom(double bed), bedroom(double bed), bedroom(single bed)

Free cancellation

from 90 € per night / night

4.5

prices from 91€ per night

View

Casciano Val di Pesa

Belvilla by OYO La Romola

5 guests

80 m²

1 bedroom

11 reviews

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 205 € per night / night

4.5

prices from 205€ per night

View

Holiday Home in Chianti with Pool & Terrace

Castelfranco di Sopra

Holiday Home in Chianti with Pool & Terrace

2 guests

45 m²

1 bedroom

27 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 73 € per night / night

4.3

prices from 73€ per night

View

Castelfranco Piandiscò

Hillside Retreat with a View

5 guests

80 m²

3 bedrooms

93 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 107 € per night / night

4.1

prices from 108€ per night

View

Cavriglia

Serene Chianti Retreat

4 guests

90 m²

2 bedrooms

63 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 97 € per night / night

4.4

prices from 97€ per night

View

Castelfranco di Sopra

Apartment in Chianti near Florence

12 guests

230 m²

6 bedrooms

31 reviews

Free cancellation

Ground floor: (Large kitchen(TV(international television channels, no dutch television channels)

Free cancellation

from 312 € per night / night

4.4

prices from 312€ per night

View

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 118€ night

August 2026

4.5

Wine Tastings, Hills and Tuscan home

Casciano Val di Pesa

A great spot for families! The play equipment kept the kids busy, and the high chair made meals easier, The shared garden is lovely, and we enjoyed the nearby restaurant's delicious food, It's a peaceful place to unwind after a day of exploring,

from 107€ night

August 2026

4.5

A Vineyard Apartment Retreat

Greve in Chianti

View German

Anyone traveling through Chianti should definitely stop here. Good value for money, adequate size for two people with additional beds if needed, and the pool invites you to linger on warm days.

from 31€ night

More inspiration for your vacation planning

Vacation ideas in Chianti

Dog friendly holidays in Chianti

holiday homes with pool 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:

August - Ø 239€/night

Best chances for available stays:

October - 50% available

Lowest availability:

August - only 20% available

Holiday home prices in Chianti

198€ for 12 Sep - 19 Sep

177€ Yearly average

200

150

100

September

Sep

October

Oct

November

Nov

December

Dec

January

Jan

February

Feb

March

Mar

April

Apr

May

June

Jun

July

Jul

August

Aug

Average price per night in €

Holiday home availability in Chianti

17% for 12 Sep - 19 Sep

38% Yearly average

100

September

Sep

October

Oct

November

Nov

December

Dec

January

Jan

February

Feb

March

Mar

April

Apr

May

June

Jun

July

Jul

August

Aug

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

38 offers

Possible discounts

up to 35%

Min. price per night

from 41 €

Popular amenities

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

Pets allowed

25 offers

Accommodations with pool

34 offers

Frequently asked questions

FAQs

How much does a holiday accommodation cost in Chianti?

From 41 € you can book our accommodations in Chianti and stay in an average of 115 m² (holiday houses) and 60 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 Castelfranco Piandiscò. If you spend your vacation here, you can rent a beautiful accommodation from 41 € 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 25 accommodations that allow pets. Dog owners feel particularly comfortable in Casciano Val di Pesa, Castelfranco di Sopra and Radda in Chianti.

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

38 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?

Add to wish list

Create wish list