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

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4,069 Holiday homes

35

Villa Siena - Ville di Corsano villa sleeps 20

Province of Siena / Ville di Corsano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a se cluded parkland in the hills of Tuscany. The theme of the outdoors continues in the elegant drawing room, formerly a ballroom, whose vaulted ceiling and wal  …see more

from £585 / night

£4095 - £6250 / week

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from £585 / night

17

Holiday Resort in Montepulciano M - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £48 / night

£332 - £694 / week

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from £48 / night

(6) Very Good 

24

Villa Caprera. Casa Borgianni - Caprera farmhouse sleeps 6

Siena / Caprera

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
A stylish apartment close to Siena ancient city walls, still surrounded by olive groves and fields; ideal for visitors looking for a quite lodge. The farmhouse is part of a unique Liberty village built by Garibaldi's doctor in 1880. Local shops are at walking dista  …see more

from £130 / night

£845 - £1078 / week

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from £130 / night

(19) Excellent 

49

Lovely detached cottage with view of San Gimignano - San Gimignano cottage sleeps 5

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy hom  …see more

from £52 / night

£363 / week

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from £52 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £190 / night

£949 / week

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from £190 / night

9

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Ask about pets

 …see more

from £61 / night

£388 / week

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from £61 / night

(1) Excellent 

7

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £52 / night

£363 / week

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from £52 / night

(5) Very Good 

15

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £51 / night

£345 - £563 / week

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from £51 / night

19

Fern Cottage (v044) - Cetona cottage sleeps 10

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This charming cottage is made up of a kitchen, a living room with fireplace, a dining room, a study, a guest bathroom and a double bedroom with en-suite bathroom with shower on the ground floor. On the first floor there is a double bedroom with en-suite with shower,  …see more

from £324 / night

£2268 - £2664 / week

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from £324 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £78 / night

£544 / week

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from £78 / night

20

chianti castle near Siena B3 - Castelnuovo Berardenga apartment sleeps 3

Province of Siena / Castelnuovo Berardenga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle. The origins of the Castle date back to 1070, but follow  …see more

from £65 / night

£363 - £595 / week

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from £65 / night

(2) Excellent 

40

Casa Lorenzo: Charming Tuscan house,pool, AC,WiFi - San Giovanni d'Asso villa sleeps 5

Province of Siena / San Giovanni d'Asso

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Lorenzo is a small indipendent antique house suitable for 5 +1. "what a beautiful charming house you have;we expecially enjoyed the view from the pool ;unparalleded beauty! San Giovanni is a wonderful little town..although we enjoyed all of our day excursion to Mon  …see more

from £207 / night

£1449 - £2018 / week

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from £207 / night

(1) Good 

33

Appartamento Gaiole 40 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Appartamento Gaiole 40 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £92 / night

£640 - £981 / week

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from £92 / night

39

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £74 / night

£345 / week

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from £74 / night

(1) Excellent 

22

Holiday Apartments near Pienza - Torrita di Siena farmhouse sleeps 3

Province of Siena / Torrita di Siena

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Swimming pool
  • Child friendly
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 £35 / night

£242 - £509 / week

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from £35 / night

(4) Excellent 

16

Pornano - Radda in Chianti apartment sleeps 3

Province of Siena / Radda in Chianti

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Ask about pets
The accommodation comprises of one double bedded bedroom with en suite bathroom and very well equipped living room/kitchen area looking out onto a pleasant flowery courtyard. Ideal for a couple seeking peace and solitude and it is centrally located to visit Florence, Si  …see more

from £50 / night

£350 / week

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from £50 / night

(1) Excellent 

32

The yellow house - Le Piazze house sleeps 6

Province of Siena / Le Piazze

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The house has three floors and it is simple furnished. The ground floor has a living room with a kitchen and a double bedroom with bathroom. In the second floor there's a double bedroom with a beautiful panorama view and a big bathroom with a nice bathtub in the centre.  …see more

from £43 / night

£259 - £380 / week

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from £43 / night

35

Casa Oliveto - Castelmuzio villa sleeps 10

Province of Siena / Castelmuzio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
When Eric and Kathy decided they wanted to settle in Tuscany and provide people with the sort of holidays they themselves had always dreamed of - but had rarely been able to find - they knew they had found the ideal property in Castelmuzio for many reasons, amongst whic  …see more

from £367 / night

£2565 - £4095 / week

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from £367 / night

20

Province of Siena / Chiusdino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

 …see more

from £370 / night

£2587 - £3276 / week

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from £370 / night

(1) Excellent 

13

Province of Siena / Chianciano Terme

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £39 / night

£259 / week

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from £39 / night

13

Province of Siena / Poggibonsi

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £57 / night

£388 - £604 / week

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from £57 / night

100

Cortona 15664 - Montepulciano villa sleeps 13

Province of Siena / Montepulciano

5 13 7 nights min

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
Charming share of an independent Tuscan villa rental affording extensive views over the surrounding landscape. The villa rental, offering tastefully furnished interiors, is quietly situated in a short distance from the lovely Tuscan town of Cortona (15 km). Distances: f  …see more

from £143 / night

£998 - £2220 / week

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from £143 / night

100

Vino Nobile - Giardino - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Located amidst the enchanting garden of the property, this independent cottage in Montepulciano affords a dining area and a living room with fireplace and double sofa bed, a kitchen with its own breakfast area, and a double bedroom with its en-suite bathroom equipped wi  …see more

from £104 / night

£647 - £845 / week

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from £104 / night

(5) Excellent 

24

Tuscan-style apartment in spectacular surroundings, shared outdoor pool, sleeps up to 6 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Podere Torricchi is in a typical tuscan landscape characterised by hills with olive trees and mediterrenean bush. Podere Torricchi is a group of converted farm buildings. The apartment has been newly restored in a traditional Tuscan style.Gambassi Terme and San Gimignan  …see more

from £61 / night

£423 - £992 / week

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from £61 / night

(5) Excellent 

49

I MELOGRANI I:5 BDR Tuscan villa,view,pool ,WiFi - San Giovanni d'Asso villa sleeps 10

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, "casale" with a large fenced swimming pool (5x12 mt), 1km away (walking  …see more

from £468 / night

£3276 - £4225 / week

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from £468 / night

28

Villa San Biagio - Montepulciano villa sleeps 16

Province of Siena / Montepulciano

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa San Biagio is situated close to the hilltop town of Montepulciano renowned for its historical importance and for its wine Nobile. This magnificent country house is one of the most exclusive and stunning farmhouses in the area. The restoration works carefully prese  …see more

from £539 / night

£3772 - £5927 / week

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from £539 / night

(3) Excellent 

35

The Notary's House - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Small charming flat, old residence of householder's great-grandfather, Notary in Montepulciano. Recently wholly restructured, very quiet, in a very beautiful position: in the centre of town, but facing the walls of the city, in a dominant position.Two nice bedrooms, sma  …see more

from £61 / night

£345 - £518 / week

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from £61 / night

(1) Excellent 

32

I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi - San Giovanni d'Asso villa sleeps 6

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
I MELOGRANI II is a section of a villa settled in the heart of Siena countryside.WHEN THIS PART OF THE HOUSE IS RENTED THE OTHER PART REMAINS CLOSED AND VACANT. This beautiful house is surrounded by a fenced olive grove with private pool (6x 5), lawn, stunning view on  …see more

from £281 / night

£1966 - £2535 / week

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from £281 / night

(2) Excellent 

16

Province of Siena / Sinalunga

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

 …see more

from £156 / night

£1026 - £1156 / week

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from £156 / night

(1) Excellent 

25

Murlo / Casciano di Murlo

5 11 3 nights min

  • 5 bedrooms
  • Sleeps 11
  • 3 nights min
  • Nearest beach 70 km
  • Child friendly
  • Private garden

 …see more

from £76 / night

£535 / week

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from £76 / night

(7) Very Good 

24

Delightful holiday house at the edge of Tuscan village of Casciano di Murlo, features private garden, terrace and pool - Casciano di Murlo house sleeps 5

Murlo / Casciano di Murlo

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Situated at the edge of the village of Casciano di Murlo, about 20 km away from Siena, in the heart of the gorgeous Tuscan countryside. Lovely views over the hills, private veranda with garden furniture and barbecue. Very tranquil location.The house (about 55 square met  …see more

from £57 / night

£371 - £475 / week

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from £57 / night

(3) Good 

5

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Pet friendly

 …see more

from £52 / night

£259 / week

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from £52 / night

100

Siena Design - Lime - Siena apartment sleeps 4

Province of Siena / Siena

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 75 km
  • Child friendly
Normal 0 21 false false false ES X-NONE X-NONE MicrosoftInternetExplorer4  …see more

from £74 / night

£513 - £694 / week

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from £74 / night

29

Il Granaio - San Gimignano villa sleeps 2

Province of Siena / San Gimignano

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden
<br>Il Granaio – San Gimignano – Tuscany<br>1 Double Bedroom – Shared Pool<br>This quaint cottage dates back to the 1400's when it was a granary, part of the farmers houses in a tiny village just 6 km from the center of San Gimignano. The &q  …see more

from £148 / night

£1035 - £1250 / week

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from £148 / night

22

Tuscan Villa Nr. San Gimignano large gardens - Campiglia dei Foci villa sleeps 8

Colle di Val d'Elsa / Campiglia dei Foci

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Nr. San Gimignano, Siena Province, Tuscany, ItalyTypical Tuscan Style Villa with Private Pool and Large Private garden.12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive GroveWonderful stone building situated in a peaceful position with a  …see more

from £161 / night

£1121 / week

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from £161 / night

11

Province of Siena / Poggibonsi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £43 / night

£294 - £475 / week

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from £43 / night

22

Casa Borgo - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £45 / night

£311 - £595 / week

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from £45 / night

12

Province of Siena / Poggibonsi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £50 / night

£345 - £561 / week

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from £50 / night

(17) Excellent 

43

Villa PoliFlora - Monticchiello apartment sleeps 6

Pienza / Monticchiello

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Classico  …see more

from £65 / night

£319 - £778 / week

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from £65 / night

(2) Excellent 

40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £108 / night

£768 - £1707 / week

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from £108 / night

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