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Holiday apartments and houses in Siena & surrounding area

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Sovicille

Palazzo a Merse

4 guests

80 m²

2 bedrooms

Free cancellation

Sustainable

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

Free cancellation

Sustainable

from 120 € per night / night

prices from 120€ per night

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Radicondoli

Apartment LA CASINA with pool

4 guests

65 m²

1 bedroom (+1)

1 review

Free cancellation

Sustainable

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

Sustainable

from 100 € per night / night

5.0

prices from 100€ per night

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Radicondoli

Apartment - LA CAPANNA with pool

4 guests

55 m²

1 bedroom

2 reviews

Sustainable

5% Early-Bird 11/01/2027 - 05/12/2028

The CAPANNA was a hayloft, where the farmers of the tuscan countryside were putting the grain back, it has been completely restructured.

Sustainable

5% Early-Bird 11/01/2027 - 05/12/2028

from 90 € per night / night

5.0

prices from 90€ per night

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10%

Radicondoli

MADONNA

12 guests

240 m²

5 bedrooms (+1)

10% Promotion 06/06/2026 - 06/13/2026

Situated on the edge of a park, just 5 minutes walk to the medieval hilltop village of Radicondoli, the property enjoys an exceptional view

10% Promotion 06/06/2026 - 06/13/2026

from 238 € per night / night

prices from 238€ per night

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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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Radicondoli

Virgilius

6 guests

90 m²

3 bedrooms

1 review

Tuscany villa with stunning views, private pool, five minutes walk to the village

from 155 € per night / night

3.3

prices from 155€ 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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Pienza

Farmhouse with private pool 8+2beds

10 guests

150 m²

4 bedrooms

3 reviews

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 € per night / night

5.0

prices from 244€ per night

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15%

Cetona

Villa Alari

14 guests

450 m²

5 bedrooms

Free cancellation

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

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 € per night / night

prices from 586€ per night

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Siena

Holiday home relaxing holiday Siena

4 guests

50 m²

2 bedrooms

from 108 € per night / night

prices from 108€ per night

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Montecastelli Pisano

COLOMBAIA

8 guests

120 m²

3 bedrooms (+3)

3 reviews

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

from 140 € per night / night

4.7

prices from 140€ per night

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San Giovanni d'Asso

Private holiday home with pool (7 + 1)

8 guests

100 m²

4 bedrooms

3 reviews

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

from 158 € per night / night

4.4

prices from 158€ per night

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Radicondoli

CASA ROSANNA

8 guests

120 m²

3 bedrooms (+1)

Charming tuscany villa with private pool and garden

from 127 € per night / night

prices from 128€ per night

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Montalcinello

VILLA DORA

13 guests

400 m²

8 bedrooms

Elegant and refined pool Villa in medieval village in Tuscany

from 400 € per night / night

prices from 400€ per night

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Colle di Val d'Elsa

CASAVICO

5 guests

95 m²

3 bedrooms

1 review

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

from 130 € per night / night

5.0

prices from 130€ per night

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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 108 € per night / night

prices from 108€ per night

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Chiusdino

La Prediera

3 guests

64 m²

1 bedroom

3 reviews

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

from 62 € per night / night

4.8

prices from 63€ per night

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Guest reviews of our holiday apartments in Siena & surrounding area

5.0

Verified guest from Tourist-paradise.com

CASAVICO

Colle di Val d'Elsa

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Relaxing vacation in the heart of Tuscany

Hello everyone.

We felt very comfortable during the week at Pietro and Erika's.

The house is in a secluded location and is only surrounded by a few farmsteads. The entire property is fenced, making it dog-friendly.

However, it should be mentioned that Boscona is situated in the middle of a hunting area, and we heard distinct gunshots on some evenings. This may be a consideration for owners of anxious pets.

Otherwise, the house is well-equipped. We used the pool; the pool robot needs to be turned on by the tenants once in the evening.

The water temperature and water pressure in the sanitary facilities were good.

There are a total of 3 rooms for up to 5 people. It can be a bit cramped for taller individuals on the upper floor, as the ceilings are relatively low.

The kitchen is well-equipped, with a dishwasher and washing machine available.

The location of the house allows for excursions into the heart of Tuscany, St. Gimignano, Siena, Volterra can be reached within 30 minutes. Florence or the beach of Marina di Bibona takes 60-90 minutes.

In nearby Cole Val D'elsa, you can find supermarkets, restaurants, and opportunities for nature excursions (waterfall).

The check-in and check-out process was straightforward and familiar. Once again, great praise to Erika for the very good and prompt correspondence via WhatsApp.

We can only recommend this beautiful house, which offers an exceptional price-performance ratio.

The best travel time in terms of climate is September. In summer, there are indeed many mosquitoes.

We would love to come back!

Best regards, Felina, Nala, Tobias

from 130€ night

4.0

Verified guest from Tourist-paradise.com

COLOMBAIA

Montecastelli Pisano

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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

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