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Holiday apartments and houses in Siena & surrounding area

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Radicondoli

MADONNA

12 guests

240 m²

5 bedrooms (+1)

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

from 240 € per night / night

prices from 240€ 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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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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Gaiole in Chianti

Burg Chianti

4 guests

70 m²

2 bedrooms

5% Last-Minute 09/23/2026 - 09/30/2026

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

5% Last-Minute 09/23/2026 - 09/30/2026

from 232 € per night / night

prices from 232€ 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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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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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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Torrita di Siena

Casa Murlo

4 guests

75 m²

1 bedroom (+1)

1 review

Free cancellation

House in a farmhouse in the Tuscan countryside, with private garden, located in a panoramic position

Free cancellation

from 100 € per night / night

5.0

prices from 100€ per night

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Radicondoli

Apartment LA CASINA with pool

4 guests

65 m²

1 bedroom (+1)

1 review

Free cancellation

5% Last-Minute 09/23/2026 - 09/30/2026

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 09/23/2026 - 09/30/2026

from 100 € per night / night

5.0

prices from 100€ per night

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20%

Colle di Val d'Elsa

CASAVICO

5 guests

95 m²

3 bedrooms

1 review

20% Last-Minute

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

20% Last-Minute

from 129 € per night / night

5.0

prices from 130€ 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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Radicondoli

CASA ROSANNA

8 guests

120 m²

3 bedrooms (+1)

Charming tuscany villa with private pool and garden

from 130 € per night / night

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 100 € per night / night

prices from 100€ per night

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Chianciano Terme

Raffaele

10 guests

160 m²

4 bedrooms

It is located only 13 km from Montepulciano. You will find a Coop supermarket, tennis courts, banks, petrol stations, restaurants and the post office within 6-7 km from the house.

from 421 € per night / night

prices from 421€ per night

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Sovicille

Palazzo a Merse

4 guests

80 m²

2 bedrooms

Free cancellation

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

Free cancellation

from 120 € per night / night

prices from 120€ 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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Montalcinello

VILLA DORA

13 guests

400 m²

8 bedrooms

Elegant and refined pool Villa in medieval village in Tuscany

from 378 € per night / night

prices from 378€ 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

View German

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

4.4

Verified guest from Tourist-paradise.com

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

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

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Holiday apartments and houses in Siena & surrounding area

Guest reviews of our holiday apartments in Siena & surrounding area

Relaxing vacation in the heart of Tuscany

Vacation in Tuscany

Lovely typical Tuscan holiday home

Popular regions and locations for your romantic holiday in Siena & surrounding area

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