Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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2,452 Holiday homes

1 / 24

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £89 / night

£617 - £748 / week

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from £89 / night

(5) Excellent 

1 / 46

Villa Sangimignano - Montauto farmhouse sleeps 5

San Gimignano / Montauto

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The house is the r  …see more

from £199 / night

£1453 - £1966 / week

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from £199 / night

1 / 22

Province of Siena / Torrita di Siena

7 11 7 nights min stay

  • 7 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £312 / night

£2180 / week

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from £312 / night

Featured properties

1 / 25

Holiday lodging near Pienza D - Torrita di Siena apartment sleeps 4

Province of Siena / Torrita di Siena

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £43 / night

£300 - £582 / week

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from £43 / night

(4) Excellent 

1 / 24

Pretty Tuscan cottage surrounded by stunning hills with private pool and terrace, sleeps up to 5 - Casole d'Elsa cottage sleeps 5

Province of Siena / Casole d'Elsa

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 65 km; Swimming pool; Child friendly ;
Stone cottage situated in the green, panoramic hills at 1.5 km from the hilltop town of Casole d'Elsa. Accommodation is offered on the elevated ground floor composed by a cosy leaving room with a double sofa bed and access onto a large panoramic terrace (50 m2), 1  …see more

from £80 / night

£556 - £1197 / week

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from £80 / night

(1) Excellent 

1 / 19

Suite d'Artista: Di Silvestre - Montalcino studio sleeps 2

Province of Siena / Montalcino

Studio 2 2 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Not suitable for children;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £142 / night

£988 / week

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from £142 / night

1 / 23

Province of Siena / Sovicille

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 80 km; Ask owner if suitable for children; Car essential;
 …see more

from £86 / night

£300 / week

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from £86 / night

1 / 24

chianti wine estate near Siena T4C - Vagliagli apartment sleeps 4

Castelnuovo Berardenga / Vagliagli

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
large 2 bedroom Apartment, 2 bathrooms, with independent entrance, located in the main in villa where the owner lives. Large garden (400 square meters) . internet wi fi, sat tv, private car parking. Wonderful terrace with view over Siena. Swimming pool at 50 meters.Bre  …see more

from £257 / night

£1795 / week

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from £257 / night

1 / 5

Camera Molino della Lodola B&B - Rapolano Terme b&b sleeps 3

Province of Siena / Rapolano Terme

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Romantica camera matrimoniale/doppia con possibilità di aggiungere un letto extra per una terza persona,bagno con doccia e balcone privato con tavolo e sedie per il relax . La camera e' molto accogliente e dotata di ogni comodità per rilassarsi in assoluta privacy .  …see more

from £86 / night

£599 / week

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from £86 / night

1 / 15

Province of Siena / Gaiole in Chianti

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £62 / night

£428 / week

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from £62 / night

1 / 7

Pienza / Monticchiello

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £77 / night

£428 / week

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from £77 / night

1 / 20

Il Ciliegio - Belforte farmhouse sleeps 8

Radicondoli / Belforte

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
The main house 'Il Ciliegio' is a very old farm, dated around 1200, on the road which goes from Belforte to the sea. The house is exposed to the south, between the forest and the valley of the cultivated fields surrounded by tranquility and nature. We are not far from B  …see more

Pricing unknown

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1 / 4

"Primavera" apartment - Pienza apartment sleeps 3

Province of Siena / Pienza

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
The building includes four brand new completely independent flats, structured on two floors; they are very new and furnished in a modern manner, equipped with all comforts like a kitchen supplied with all of the tools and household appliances, colour TV-Set, autonomous  …see more

from £77 / night

£359 / week

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from £77 / night

1 / 24

Province of Siena / Palazzone

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 106 km; Swimming pool; Suitable for children age 5+;
 …see more

from £77 / night

£300 - £599 / week

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from £77 / night

1 / 11

VILLA IL POGGIO "ROSMARINO" - Sinalunga apartment sleeps 4

Province of Siena / Sinalunga

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
The third of the apartments of the Villa Poggio called Rosmarino.Also like other offers all the services you need to enjoy your stay and holidays in total peace and relaxation.For more information on services available in the apartment and usufruibili by visitors can ge  …see more

from £98 / night

£683 - £941 / week

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from £98 / night

1 / 30

Province of Siena / Castellina In Chianti

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Not suitable for children; Car essential; No pets allowed;
 …see more

from £77 / night

£428 / week

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from £77 / night

(1) Excellent 

1 / 12

Sienahomeandsailing-Green apartment - Siena apartment sleeps 4

Province of Siena / Siena

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Car not necessary; Air conditioning;
Green apartment is located at ground floor and easily accessible, perfect for a family. It consists of a fully equipped kitchen where a folding sofa bed for two guests is provided, a bedroom with a double bed, a bathroom with shower, toilet, hairdryer, washing machin  …see more

from £38 / night

£264 / week

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from £38 / night

(1) Very Good 

1 / 12

Province of Siena / Colle di Val d'Elsa

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Not suitable for children; Car advised; No pets allowed;
 …see more

from £39 / night

£240 / week

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from £39 / night

1 / 28

Holiday lodging near Pienza P5 - Torrita di Siena apartment sleeps 5

Province of Siena / Torrita di Siena

1 5 7 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £47 / night

£325 - £582 / week

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from £47 / night

1 / 5

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £73 / night

£509 / week

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from £73 / night

1 / 5

Province of Siena / Rocca d'Orcia

3 7 2 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £103 / night

£428 / week

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from £103 / night

(7) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6 - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Child friendly ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £84 / night

£565 - £941 / week

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from £84 / night

1 / 17

Apartment bruco - Colle di Val d'Elsa farmhouse sleeps 4

Province of Siena / Colle di Val d'Elsa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
The farm house Verniano is a petting farm and an organic farm, a family immersed in the typical rural Tuscan landscape. Perfect for families, couples and groups of friends.The farm consists of five apartments, obtained from recent restructuring of the small village of &  …see more

Pricing unknown

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1 / 21

Rapolano Terme / Serre di Rapolano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 124 km; Child friendly ; Car advised;
 …see more

from £82 / night

£569 / week

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from £82 / night

1 / 14

Province of Siena / Poggibonsi

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £52 / night

£359 / week

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from £52 / night

(1) Excellent 

1 / 23

Tuscan Villa Argiano 1-2room ,Montepulciano, B&B - Montepulciano villa sleeps 6

Province of Siena / Montepulciano

4 6 2 nights min stay

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Ask owner if suitable for children;
in Villa Argiano in Montepulciano, we have several possibilities : B&B in Argiano's villa rooms ( three ) or self catering apartments ( two + one extra room ) in farmhouse fattoriadiargiano dot it. In this beautiful Villa, were we live , at the second floor of th  …see more

from £69 / night

£479 / week

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from £69 / night

(1) Excellent 

1 / 24

Casa Giovanni - San Giovanni d'Asso villa sleeps 5

Province of Siena / San Giovanni d'Asso

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Italian village rental - This charming historic residence is part of a larger building, located in the village of San Giovanni d'Asso, just beyond the original castle walls and a short walk to the centre.With origins dating back to the 15th century this property ce  …see more

from £240 / night

£1680 - £2360 / week

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from £240 / night

1 / 13

La Tinaia - beautiful 1 bedroom cottage & garden - Castellina In Chianti cottage sleeps 2

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
Podere Patrignone is a beautiful old 15th Century estate ('podere') which has been lovingly and tastefully restored. Patrignone is set on top of it's own hill reached by a long, winding private road that ends at Patrignone. It is set in 150 acres of fores  …see more

from £129 / night

£770 - £949 / week

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from £129 / night

1 / 16

Luxury Chianti apartment with shared pool, private garden, barbecue - Castellina In Chianti castle sleeps 4

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Come to the heart of the Chianti region to discover a wonderfully charming inn and agritourism facility that offers hotel-like amenities in elegant apartment suites, set in the evocative atmosphere of the Tuscan hills. Resting on a rolling hill, the Borgo is located  …see more

from £136 / night

£946 - £1311 / week

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from £136 / night

1 / 12

Province of Siena / Montalcino

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £103 / night

£684 / week

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from £103 / night

1 / 36

Province of Siena / Radicondoli

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 70 km; Child friendly ; Car advised;
 …see more

from £129 / night

£599 / week

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from £129 / night

1 / 20

Villa Fontecaresino 2 - Montegrossi house sleeps 4

Gaiole in Chianti / Montegrossi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from  …see more

from £73 / night

£941 / week

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from £73 / night

1 / 17

Pienza / Monticchiello

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £103 / night

£642 / week

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from £103 / night

1 / 26

Holiday lodging near Pienza S - Torrita di Siena apartment sleeps 4

Province of Siena / Torrita di Siena

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £43 / night

£300 - £556 / week

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from £43 / night

1 / 9

apartment in Montefollonico - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Ask about pets;
Villa Chiara is a self-catering accommodation located in Montefollonico. Free WiFi access is available. The apartment will provide you with a TV and a seating area. Complete with a refrigerator, the dining area also has kitchenware and a coffee machine. Featuring a show  …see more

Pricing unknown

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1 / 47

La Grancia Country Resort Apt3 - Montisi fort sleeps 5

Province of Siena / Montisi

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £155 / night

£1059 - £1156 / week

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from £155 / night

1 / 11

Torrita di Siena flats O - Torrita di Siena apartment sleeps 3

Province of Siena / Torrita di Siena

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the villag  …see more

from £62 / night

£206 - £432 / week

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from £62 / night

1 / 20

Buonconvento / Chiusure

6 14 1 night min stay

  • 6 bedrooms
  • Sleeps 14
  • 1 night min stay
Key info: Nearest beach 87 km; Swimming pool; Child friendly ;
 …see more

from £77 / night

£535 / week

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from £77 / night

1 / 9

Province of Siena / Ville di Corsano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

Pricing unknown

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1 / 12

Montepulciano / Abbadia di Montepulciano

3 7 1 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; Car advised; Pet friendly;
 …see more

from £52 / night

£257 / week

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from £52 / night

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