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Holiday apartments and houses in Siena & surrounding area

COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
Montecastelli Pisano

COLOMBAIA

8 guests
120 m2
3 bedrooms (+3)

Typical Tuscan country farmhouse converted into a perfect holiday house for families or groups of friends

from 140 € / night
4.7
prices from 140€ per night
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20%
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
Colle di Val d'Elsa

CASAVICO

5 guests
95 m2
3 bedrooms

Beautiful cottage with private pool ideal for spending a relaxing holiday in Tuscany

20% Last-Minute

from 129 € / night
5.0
prices from 130€ per night
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MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
Radicondoli

MADONNA

12 guests
240 m2
5 bedrooms (+1)

Characteristic stone farmhouse with adjoining barn, located on top of a hill with breathtaking views

from 240 € / night
prices from 240€ per night
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Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Gaiole in Chianti

Ancient tower with private pool 5+1

6 guests
120 m2
3 bedrooms

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 € / night
4.9
prices from 200€ per night
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Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
San Giovanni d'Asso

Private holiday home with pool (7 + 1)

8 guests
100 m2
4 bedrooms

Rustic stone house in the Crete Senesi in a panoramic position, fenced garden with private pool, barbecue, fireplace, satTV, covered parking

from 158 € / night
4.4
prices from 158€ per night
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VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
Montalcinello

VILLA DORA

13 guests
400 m2
8 bedrooms

Elegant and refined pool Villa in medieval village in Tuscany

from 392 € / night
prices from 392€ per night
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Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Pienza

Farmhouse with private pool 8+2beds

10 guests
150 m2
4 bedrooms

Rustic country house in the province of Siena, panoramic location, 500 m² garden, 150 m² living space, 4 bedrooms, 4 bathrooms, pool, WIFI, satellite TV, fireplace, bicycles

from 244 € / night
5.0
prices from 244€ per night
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CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
Radicondoli

CASA ROSANNA

8 guests
120 m2
3 bedrooms (+1)

Charming tuscany villa with private pool and garden

from 130 € / night
prices from 130€ per night
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15%
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Cetona

Villa Alari

14 guests
450 m2
5 bedrooms

Villa for 14 people with private pool and hot tub. Located on a 40-hectare farmstead, with vineyards, olive groves, and private forest.

Free cancellation

15% Promotion 11/16/2026 - 03/24/2027

from 585 € / night
prices from 586€ per night
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HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
Colle di Val d'Elsa

HUT OF SILVIA

4 guests
50 m2
1 bedroom (+1)

La Capanna di Silvia is located in a panoramic and strategic location, within easy reach of the most beautiful towns and villages in Tuscany

from 105 € / night
prices from 105€ per night
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Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Sovicille

Palazzo a Merse

4 guests
80 m2
2 bedrooms

Holiday home for a relaxing vacation Sovicille: 80 m², 2 rooms, for up to 4 people in Tuscany.

Free cancellation
from 120 € / night
prices from 120€ per night
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5%
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Radicondoli

Apartment LA CASINA with pool

4 guests
65 m2
1 bedroom (+1)

The apartment LA CASINA is part of an ancient farmhouse immersed in the green of the Tuscan hills and in the center of a wildlife reserve.

Free cancellation

5% Last-Minute 11/08/2026 - 11/15/2026

from 100 € / night
5.0
prices from 100€ per night
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La Prediera
La Prediera
La Prediera
La Prediera
La Prediera
Chiusdino

La Prediera

3 guests
64 m2
1 bedroom

Tuscany, near Siena, idyllic location in the middle of nature, culture and tranquillity

from 62 € / night
4.8
prices from 63€ per night
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Guest reviews of our holiday apartments in Siena & surrounding area

4.4

Verified guest from Tourist-paradise.com

Vacation in Tuscany

Private holiday home with pool (7 + 1)

San Giovanni d'Asso

View German

Vacation in Tuscany

Lovingly furnished house with its own pool (the highlight!)
Pure relaxation for stressed people with a great view of the surroundings. Delicious honey can be purchased next door.
The owners are super nice and caring. All questions were answered immediately, generally always a listening ear!
We were happy to be guests here - we really liked it.
Tip -> an off-road vehicle is advantageous.


from 158€ night
4.0

Verified guest from Tourist-paradise.com

Lovely typical Tuscan holiday home

COLOMBAIA

Montecastelli Pisano

View German

Lovely typical Tuscan holiday home

The house is located in an absolutely quiet location. The beautiful Tuscan countryside is easily accessible. It is a 40-minute drive to the sea. Great private pool. Excursions to Siena and Volterra are doable in 45-60 minutes and worthwhile. Beach tip: Dog beach near Cecina. (There were hardly any dogs when we were there. It is a free beach, nicely located.) The house had everything you needed. Sufficient cutlery, etc. Definitely recommended.


from 140€ night
5.0

Beautiful country house in wonderful nature

Apartment LA CASINA with pool

Radicondoli

View German

Beautiful country house in wonderful nature

We felt completely at home in the house La Cassettina.
It is ideally suited for people who like to find peace and relaxation. The furnishings of the flat are very cosy, designed in the old Tuscan style. Excursions to the nearer or further surroundings can be started very well from here, as the larger connecting road can be reached after a few kilometres. The swimming pool area is wonderful and very clean. The two landlords
Grazia and Rossano are super nice and they were always helpful in all our matters. We can fully recommend La Cassettina.


from 100€ night

Popular regions and locations for your long term rental in Siena & surrounding area

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