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

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4,112 Holiday homes

(4) Excellent 

17

Charming, restored house in southeast Tuscany, features log fire and balcony, sleeps 4 - Cetona house sleeps 4

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
Old world charm, character and beauty abound in this restored townhome in the the quaint village of Cetona in southeast Tuscany. The home is located in the centro storico (the original, old section) and is over 300 years old. Casa Perfetta is located on a corner which  …see more

from £61 / night

£423 / week

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from £61 / night

100

Villa Gardenia - Classic Room - Siena apartment sleeps 3

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
These 4 classic rooms boast the typical Tuscan décor. They can accommodate up to 2 people each and they all afford comfortable beds, private and fully equipped bathrooms, television and telephone, among other amenities. Some of them offer an extra bed upon reques  …see more

from £77 / night

£538 - £960 / week

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from £77 / night

(1) Very Good 

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £120 / night

£474 - £715 / week

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from £120 / night

(2) Very Good 

10

Cosy Tuscan villa for friends or family - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Splendid three bedroom two bathroom villa located right outside of San Gimignano. Absolut privacy and quiet location !! Incredible private pool with a panoramic position over the Tuscan landscape Three double bedrooms - perfect for couples or friends travelling to  …see more

from £138 / night

£949 - £1207 / week

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from £138 / night

(2) Excellent 

35

Agriturismo Sammonti - Monteriggioni farmhouse sleeps 2

Province of Siena / Monteriggioni

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions.Th  …see more

from £65 / night

£432 - £475 / week

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from £65 / night

19

Campiglia d'Orcia SI - ITS171 - Castiglione D'Orcia villa sleeps 4

Province of Siena / Castiglione D'Orcia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Situated in Tuscany, this wonderful property is the ideal location for exciting escapes in Italy. There are 1 double bed and 2 single beds in the villa, so it can comfortably host up to 4 people. There are also 3 bathrooms for individual comfort and privacy. Modern conv  …see more

from £57 / night

£396 - £544 / week

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from £57 / night

(1) Excellent 

9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

 …see more

from £35 / night

£613 - £923 / week

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from £35 / night

20

Wisteria Farm (V036) - Pienza farmhouse sleeps 8

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The farmhouse, set in one of the most fascinating areas of the south of Sienese territory, between Pienza and Montepulciano, shows sober, almost austere lines. Its placing, the group of cypresses, its position on a high ground which raise the whole valley, makes it the  …see more

from £355 / night

£2483 - £3061 / week

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from £355 / night

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Pet friendly

 …see more

from £44 / night

£302 / week

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from £44 / night

(3) Excellent 

22

Granaio 6 - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San  …see more

from £36 / night

£250 - £854 / week

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from £36 / night

20

CAMINO apartment - Monticiano apartment sleeps 2

Province of Siena / Monticiano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Romantic and charming 02 people 50 sq.mt first floor apartment in traditional Tuscan villa. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Double bed. En suite bathroom with shower. Designer ceiling fan for summer cooling. Essential foo  …see more

from £111 / night

£768 - £794 / week

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from £111 / night

(5) Excellent 

35

Monticiano / Tocchi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£396 - £879 / week

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from £61 / night

4

Province of Siena / Radicondoli

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Nearest beach 55 km
  • Suitable for children age 5+
  • Private garden

 …see more

from £61 / night

£432 / week

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from £61 / night

(3) Excellent 

25

Province of Siena / Vivo d'Orcia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Ski
  • Child friendly

 …see more

from £61 / night

£388 / week

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from £61 / night

(32) Excellent 

24

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

18

Villa Fontecaresino 1 - Montegrossi villa sleeps 9

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
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, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £111 / night

£776 - £1983 / week

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from £111 / night

20

The Convent (v019) - Radicofani villa sleeps 12

Province of Siena / Radicofani

1 12 7 nights min

  • 1 bedroom
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This was an old monastery during the first half of the sixteenth century and went on to become a summer residence for the friars of Monte Oliveto Maggiore. It enjoys beautiful views across a valley. Old farmhouse, well restored, divided into three apartments. Snowdrop (  …see more

from £180 / night

£1259 - £1544 / week

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from £180 / night

(3) Excellent 

24

Radicondoli / Belforte

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £199 / night

£1294 - £1552 / week

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from £199 / night

(6) Very Good 

43

Chianti house, Florence, Jacuzzi, Tuscany up to 6p - Montefienali house sleeps 6

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £47 / night

£269 - £604 / week

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from £47 / night

23

S.anna - San Giovanni d'Asso villa sleeps 7

Province of Siena / San Giovanni d'Asso

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
The farm-house is finely fitted-out, floors are in baked-clay Sienese cotto and ceilings are of traditional tile-and-beam. The layout consists of: a kitchen; a sitting-room with couches; 3 bedrooms - a triple and 2 doubles - with wrought-iron beds; and 4 bathrooms, eac  …see more

from £130 / night

£173 - £1811 / week

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from £130 / night

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £104 / night

£518 - £1121 / week

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from £104 / night

23

Medieval Village Flat - easy access - Chianciano Terme apartment sleeps 3

Province of Siena / Chianciano Terme

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask owner if suitable for children
The flat is Located at the first floor (2 flights of stairs) at the heart of Chianciano Medieval Village. Chianciano is a lovely small village. There is a basic grocery shop just downstairs, and the main COOP 5 minutes walk away. You have newspapers and tobaccos shop n  …see more

from £30 / night

£195 / week

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from £30 / night

(1) Excellent 

11

Province of Siena / Castiglione D'Orcia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £52 / night

£276 / week

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from £52 / night

20

Casa Eleonora - Gallina villa sleeps 12

Castiglione D'Orcia / Gallina

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Just South of Siena, The Val d'Orcia is UNESCO World Heritage. Its enchanting towns and villages like Montalcino and Pienza are surrounded by a sea of vines and olives whose slopes intermittently give way to deep forest of pines, chestnuts and oaks, cool and refreshing.  …see more

from £186 / night

£1294 - £2113 / week

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from £186 / night

15

Rosemary Villa (v007) - Pienza farmhouse sleeps 12

Province of Siena / Pienza

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly
Ground floor: a large dining/living room overlooking the garden, kitchen, breakfast room, small sitting room with fireplace, study, twin bedded room with en suite bathroom with tub and shower, double bedroom with en suite bathroom with shower. First floor: large lounge  …see more

from £672 / night

£4699 - £6319 / week

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from £672 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £179 / night

£1250 - £1682 / week

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from £179 / night

(2) Excellent 

22

Pienza / Monticchiello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £44 / night

£294 - £378 / week

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from £44 / night

100

Vino Nobile - Fontana - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
This enchanting suite in Montepulciano affords a dining-com-living area and a kitchen corner. The bedroom has a comfortable double bed and it affords an en-suite bathroom with whirlpool shower. The design of this suite is very peculiar, since the furniture has been crea  …see more

from £87 / night

£604 - £733 / week

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from £87 / night

5

the Hut - Montisi house sleeps 4

Province of Siena / Montisi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
La Capanna is a self-contained guest house built in local stone, perfect for a single, a couple or (for short stays) a small family. It's situated across the valley from the village of Montisi on a small rural estate, surrounded by lovely views and has a private outdoor  …see more

from £65 / night

£432 - £552 / week

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from £65 / night

5

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £113 / night

£604 / week

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from £113 / night

(3) Excellent 

16

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

 …see more

from £39 / night

£272 / week

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from £39 / night

24

Villa Gianni - Monteriggioni villa sleeps 6

Province of Siena / Monteriggioni

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa near Monteriggioni : Located in the heart of Tuscany, to the south of Florence, Villa Gianni is an attractive small  property, recently renovated and well furnished throughout. Located in wine country, there are classic Tuscan views from around the property o  …see more

from £210 / night

£1470 - £2310 / week

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from £210 / night

(2) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 km
  • Child friendly
  • Private garden

 …see more

from £104 / night

£475 - £561 / week

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from £104 / night

100

Casa Daria - La Daria - Guazzino apartment sleeps 2

Sinalunga / Guazzino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
Exterior Casa Daria is a charming apartment situated in the centre of the town of Bettole, just a few kilometres from the famous Montepulciano and Cortona, in the beautiful area of the Val di Chiana in the South of Tuscany.  The apartment, which can be fo  …see more

from £52 / night

£363 - £453 / week

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from £52 / night

100

Vino Nobile - Vigna - Montepulciano apartment sleeps 3

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
This charming cottage in Montepulciano affords a dining area and a living room with fireplace and single sofa bed, a kitchenette and a double/twin bedroom. The cottage also has its own private bathroom with shower.Outside, it features its own private terrace. The cottag  …see more

from £104 / night

£604 - £802 / week

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from £104 / night

(1) Excellent 

14

Province of Siena / Poggibonsi

2 4 1 night min

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

 …see more

from £44 / night

£302 / week

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from £44 / night

(2) Excellent 

24

Balz Tuscan farmholiday Chianti with pond - Radda in Chianti farmhouse sleeps 3

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £52 / night

£302 - £388 / week

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from £52 / night

(33) Excellent 

24

SORTOIANO apartaments in historic Tuscan property - Val di Merse apartment sleeps 5

Siena / Val di Merse

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
LAST MINUTE OFFER IN SEPTEMBER !! OFFERTE LAST MINUTE A SETTEMBRE !! FURTHER AVAILABILITY DESPITE THE BOOKING CALENDAR, PLEASE, LET'S CONTACT US! The property dates back to the 14th century and for generations has been part of the property Santini, once farmers. The  …see more

from £39 / night

£259 - £302 / week

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from £39 / night

24

Casa Chianti - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
A cosy and lovingly furnished 1 bedroom apartment 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 wonderful SienaT  …see more

from £45 / night

£311 - £535 / week

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from £45 / night

100

Foiano Della Chiana 15663 - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
Beautiful 5-hectare estate in Tuscany, a villa for wedding celebration and holidays, comprising a farmhouse of 140 m2 and an outbuilding of 60 m2 which have been skilfully restored and turned into a delightful independent villa offering tastefully and refined furnished  …see more

from £159 / night

£1109 - £2184 / week

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from £159 / night

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