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7 special offers for Holiday apartments & homes in Siena & surrounding area

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13%

Radicondoli

MADONNA

12 guests

240 m²

5 bedrooms (+1)

13% 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

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

from 238 € per night / night

prices from 238€ per night

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15%

Montalcinello

Villa Montebello

18 guests

800 m²

8 bedrooms (+1)

15% Promotion 06/05/2026 - 06/06/2026

from 575 € per night / night

prices from 575€ 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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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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20%

Asciano

Holiday flat family holiday Asciano

6 guests

80 m²

3 bedrooms

1 review

20% Promotion 06/05/2026 - 07/03/2026

from 201 € per night / night

4.4

prices from 201€ per night

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10%

Siena

Holiday flat family holiday Siena

6 guests

85 m²

2 bedrooms

10% Promotion 08/12/2026 - 08/28/2026

from 135 € per night / night

prices from 136€ per night

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20%

Siena

Holiday home relaxing holiday Siena

4 guests

90 m²

2 bedrooms

1 review

20% Promotion 10/03/2026 - 11/27/2026

from 160 € per night / night

5.0

prices from 160€ per night

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Accommodations near Siena & vicinity

These accommodations match your search but are located outside of the destination area.

10%

8 km from Siena & vicinity

Casole d'Elsa

PEPERONCINO

4 guests

85 m²

2 bedrooms

3 reviews

10% Promotion 06/05/2026 - 06/26/2026

Charming cottages with private pool in Siena area

10% Promotion 06/05/2026 - 06/26/2026

from 125 € per night / night

4.7

prices from 125€ per night

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20%

11 km from Siena & vicinity

Casole d'Elsa

THE CHAMPION

12 guests

350 m²

6 bedrooms

1 review

20% Promotion 06/20/2026 - 06/27/2026

Hilltop Tuscan Villa located between Siena and Pisa, stunning views, geogeous pool and garden, sleeps 12

20% Promotion 06/20/2026 - 06/27/2026

from 243 € per night / night

3.8

prices from 243€ per night

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10%

13 km from Siena & vicinity

Casole d'Elsa

PANORAMIC HOUSE

4 guests

100 m²

2 bedrooms

10% Promotion 06/05/2026 - 06/19/2026

The property is a lovingly renovated Tuscany cottage with private pool and garden for al fresco dining, ideal for families and couples seeking relaxation

10% Promotion 06/05/2026 - 06/19/2026

from 155 € per night / night

prices from 155€ per night

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10%

13 km from Siena & vicinity

Casole d'Elsa

VILLA CAMILLA

5 guests

110 m²

2 bedrooms (+1)

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

Cozy renovated farmhouse surrounded by a large garden, completely enclosed and provided with a private 5 x 10 large swimming pool

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

from 130 € per night / night

prices from 130€ per night

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15%

32 km from Siena & vicinity

Grosseto

Ferienhaus mit eigenem Pool

8 guests

120 m²

4 bedrooms

1 review

Free cancellation

15% Promotion 06/05/2026 - 06/30/2026

Detached country house in the middle of nature, in the province of Grosseto, panoramic location, very large property (5 ha) with private pool, fireplace, wifi, TV, barbecue, fenced garden

Free cancellation

15% Promotion 06/05/2026 - 06/30/2026

from 235 € per night / night

5.0

prices from 236€ per night

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10%

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36 km from Siena & vicinity

Cecina

Serenella-Montescudaio Cecina

4 guests

47 m²

1 bedroom (+1)

56 reviews

Free cancellation

Sustainable

Quiet 2-room ground floor apartment, spacious amenities, sunny terrace 180° PANORAMA, garden. Children-seniors welcome. Air conditioning, dishwasher+washing machine, fireplace, SatTV, grill, bicycles.

Free cancellation

Sustainable

from 112 € per night / night

5.0

prices from 113€ per night

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29%

42 km from Siena & vicinity

Bibbona

Holiday home relaxing holiday Bibbona

7 guests

32 m²

3 bedrooms (+1)

2 reviews

29% Promotion 06/05/2026 - 06/06/2026

from 79 € per night / night

4.5

prices from 79€ per night

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29%

42 km from Siena & vicinity

Bibbona

Holiday home relaxing holiday Bibbona

7 guests

32 m²

3 bedrooms (+1)

2 reviews

29% Promotion 06/05/2026 - 06/06/2026

from 79 € per night / night

4.3

prices from 79€ per night

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13%

43 km from Siena & vicinity

Grosseto

Romantic holiday home with pool

4 guests

85 m²

2 bedrooms

1 review

13% Promotion 06/27/2026 - 07/03/2026

Rustic country house, fenced garden with pool, completely private - no other people, close to the wide natural beaches of Alberese and Marina di Grosseto, built-in barbecue, WIFI

13% Promotion 06/27/2026 - 07/03/2026

from 207 € per night / night

4.6

prices from 207€ per night

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14%

44 km from Siena & vicinity

Cecina

Holiday home relaxing holiday Cecina

5 guests

32 m²

2 bedrooms (+1)

2 reviews

14% Promotion 06/05/2026 - 06/27/2026

from 97 € per night / night

5.0

prices from 98€ per night

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14%

44 km from Siena & vicinity

Cecina

Holiday home relaxing holiday Cecina

5 guests

24 m²

2 bedrooms (+1)

2 reviews

14% Promotion 06/05/2026 - 06/27/2026

from 92 € per night / night

4.6

prices from 93€ per night

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14%

44 km from Siena & vicinity

Cecina

Holiday home relaxing holiday Cecina

4 guests

26 m²

1 bedroom (+1)

2 reviews

14% Promotion 06/05/2026 - 06/27/2026

from 71 € per night / night

4.8

prices from 72€ per night

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14%

44 km from Siena & vicinity

Cecina

Holiday home relaxing holiday Cecina

5 guests

34 m²

2 bedrooms (+1)

3 reviews

14% Promotion 06/05/2026 - 06/27/2026

from 102 € per night / night

4.6

prices from 103€ per night

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14%

44 km from Siena & vicinity

Cecina

Holiday home relaxing holiday Cecina

5 guests

24 m²

2 bedrooms (+1)

2 reviews

14% Promotion 06/05/2026 - 06/27/2026

from 81 € per night / night

4.6

prices from 82€ per night

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14%

44 km from Siena & vicinity

Cecina

Holiday home relaxing holiday Cecina

5 guests

24 m²

2 bedrooms (+1)

2 reviews

14% Promotion 06/05/2026 - 06/27/2026

from 84 € per night / night

4.8

prices from 85€ per night

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Guest reviews of our holiday apartments in Siena & surrounding area

5.0

Holiday home relaxing holiday Siena

Siena

View German

The holiday home is perfect for an unforgettable holiday. The owner Michele is very friendly, looks after his guests perfectly and gives lots of tips for things to do in the area if required. The house and grounds are very clean and well maintained. The equipment is excellent and leaves nothing to be desired. Our family enjoyed every minute in this oasis.

from 160€ 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