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Province of Siena

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806 Holiday homes

(1) Very Good 

35

Province of Siena / San Gimignano

7 10 3 nights min

  • 7 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Private garden

 …see more

from £244 / night

£1597 - £1849 / week

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from £244 / night

(15) Excellent 

23

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“We enjoyed our holidays in this beautiful agriturismo” We have spent two weeks in Fernando Mattii's agriturismo. The site is very clean and very well maintained. Fernando Mattii was always helpful when we needed anything and he even brought us some wo  …see more

from £76 / night

£421 - £631 / week

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from £76 / night

22

Chiusi holiday villa accommodation

Province of Siena / Chiusi

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £240 / night

£1681 - £3782 / week

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from £240 / night

(4) Excellent 

19

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“lovely and peaceful” Il Giardino is a wonderful, intimate place. The house is not huge - but it is perfect for a family.The outside space is so beautiful and serene - the pool and gardens and hammocks and olive groves and flowers and herbs.... We lo  …see more

from £215 / night

£1500 - £7950 / week

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from £215 / night

6

Holiday apartment letting

Casole d'Elsa / Monteguidi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Our APARTMENTS and ONE-ROOM APARTMENTS are located in the two main buildings of the Borgo; they have simple and functional furnishings, they are warm and inviting, and all rooms have their original timbered ceilings and Tuscan terracotta.  …see more

from £93 / night

£518 - £913 / week

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from £93 / night

20

Farmhouse letting in Radicondoli with shared pool

Radicondoli / Belforte

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Summer holiday rental, self-catering, romantic view, villa in Tuscany, city of art, Siena, Florence, San Gimignano, Volterra, Monteriggioni, Certaldo,Radicondoli, Belforte,San Galgano, Massa Marittima, Populonia.  …see more

Pricing unknown

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Pricing unknown

(2) Very Good 

41

Holiday barn with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
The Piaggione of Serravalle is a lively farm that is in constant action and that brings forth its daily acti  …see more

from £95 / night

£664 - £1169 / week

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from £95 / night

(1) Very Good 

18

B&b letting in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“nice place, nice people” Living for a bit in an old fashioned atmosphere. It is a confortable and friendly place to stay with your family , friends or alone both relaxing in a wonderful Tuscany landscape and travelling around to explore Reinassance  …see more

from £30 / night

£34 - £740 / week

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from £30 / night

(7) Excellent 

28

Province of Siena / Brenna

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £80 / night

£505 / week

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from £80 / night

21

Castelnuovo Berardenga / Pianella

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(6) Excellent 

24

Holiday farmhouse with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 68 km
  • Swimming pool
  • Child friendly
Ground floor of the smaller farmhouse.Accommodates up to 4Large master bedroom and a 2nd bedroom with twin beds.Big living room with fireplace, flat screen TV,a comfortable sofa and armchair. Outside a very big loggia with private BBQ for alfresco dining and relaxingOu  …see more

from £93 / night

£632 - £904 / week

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from £93 / night

10

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

4 16 Min stay varies

  • 4 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Podere Podernovo offers accommodation up to 16 people ,with all comforts,as heating, air conditioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley. You can rent the whole Podere the  …see more

from £454 / night

£2522 - £3362 / week

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from £454 / night

28

Holiday villa in Pienza

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

from £241 / night

£1681 - £5757 / week

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from £241 / night

24

Castiglione D'Orcia / Gallina

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

 …see more

from £91 / night

£636 - £950 / week

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from £91 / night

22

Province of Siena / San Gimignano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Ask about pets

 …see more

from £183 / night

£1278 - £1517 / week

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from £183 / night

(3) Excellent 

24

Radicondoli / Belforte

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £181 / night

£1261 - £1849 / week

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from £181 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Fabulous place to stay with a group of friends or family.” My Husband and I stayed here with a group of our friends for a week. It was the perfect size and location. Great for day trips to the hill towns of Tuscany or just hanging out in the cute to  …see more

from £300 / night

£1500 - £2000 / week

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from £300 / night

7

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Brunella apartment has 1 double and 1 triple bedrooms and a spacious livingroom with kitchen. It includes linen, kitchenware , microwave, coffeemaker, and even dishwasher. External pool, patios and garden are free to use. Very spacious apartment (83 sqm), original artw  …see more

from £109 / night

£799 - £1009 / week

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from £109 / night

24

Holiday apartment in Casole d'Elsa

Province of Siena / Casole d'Elsa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Private garden
LARGE 6/10 people (120 sq m.)- on two floors (ground floor/first floor)  …see more

from £173 / night

£965 - £1795 / week

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from £173 / night

(2) Excellent 

16

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £72 / night

£395 - £942 / week

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from £72 / night

(2) Excellent 

25

Holiday villa in Buonconvento

Buonconvento / Chiusure

4 9 6 nights min

  • 4 bedrooms
  • Sleeps 9
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Located in the heart of the famous Crete Senesi, Agricola Neci offers intimacy, privacy and relaxation. Just 2 km away from the Archabbey of Monte Oliveto Maggiore, it also borders with Buonconvento, just a step away from the vineyards of Brunello Montalcino. 9th Gues  …see more

from £446 / night

£2690 - £3748 / week

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from £446 / night

43

Villa rental in Castelnuovo Berardenga with shared pool

Province of Siena / Castelnuovo Berardenga

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
The Piaggione of Serravalle, at a first glance, appears as a gem naturally cast on the highest ridges of the Chianti hills of Central Tuscany, and as a jewel it shines with its authentic flavors, ancient traditions and silent stillness.Shaded and enclosed by oak woo  …see more

from £496 / night

£1849 - £3530 / week

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from £496 / night

7

Pancole holiday farmhouse rental

San Gimignano / Pancole

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
francigena, San Gimignano, Pool, Garden, relax, peace, privacy, Tuscuny, Chianti, Chiantishire, Vernaccia,The apt Tramonto is located on the first floor. From its windows you can admire wide landscape toward west.  …see more

from £53 / night

£337 / week

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from £53 / night

28

Holiday apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s  …see more

from £88 / night

£589 - £1589 / week

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from £88 / night

8

Apartment rental in Montepulciano

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Private garden
We have magnificent views, over the Val d'Orcia, Pienza, Montalcino, the Val Di Chiana Valley with its three lakes (Trasimeno, Chiusi and Montepulciano). Montepulciano is only 4 km far from here. You can easily reach the most famous cities of Tuscany and UmbriaWi-f  …see more

from £93 / night

£353 - £622 / week

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from £93 / night

6

Holiday apartment with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Our APARTMENTS and ONE-ROOM APARTMENTS are located in the two main buildings of the Borgo; they have simple and functional furnishings, they are warm and inviting, and all rooms have their original timbered ceilings and Tuscan terracotta.  …see more

from £93 / night

£510 - £1075 / week

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from £93 / night

24

Holiday farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
www.ilcellese.it  …see more

Pricing unknown

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Pricing unknown

34

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £59 / night

£379 - £395 / week

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from £59 / night

9

Colle di Val d'Elsa / Campiglia dei Foci

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £59 / night

£295 - £437 / week

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from £59 / night

24

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

 …see more

from £68 / night

£295 / week

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from £68 / night

(11) Excellent 

22

Villa rental in Chiusi

Province of Siena / Chiusi

5 9 1 night min

  • 5 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“All around fabulous vacation !” We were a group of six and there was plenty of room for everyone. when we arrived, Flaminia our host arranged a lovely welcoming snack and wine, explained everything we needed to know. The location of the villa w  …see more

from £211 / night

£1429 / week

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from £211 / night

15

Holiday farmhouse rental

Province of Siena / Radicofani

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
We offer hospitality in two delightful double rooms, each with private bath, elegantly furnished exclusively with antique furniture. Each room is accessed directly from the garden with a separate entrance to ensure complete privacy.From the private garden and decora  …see more

from £59 / night

£295 - £437 / week

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from £59 / night

13

Province of Siena / Trequanda

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 34 km
  • Private garden

 …see more

from £111 / night

£858 / week

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from £111 / night

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has  …see more

from £384 / night

£2299 - £3969 / week

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from £384 / night

25

Siena holiday villa rental

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms f  …see more

from £421 / night

£2017 - £2942 / week

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from £421 / night

(2) Excellent 

21

Holiday farmhouse with shared pool in Radicondoli

Province of Siena / Radicondoli

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Beautiful house, amazing scenery!” We stayed here for two weeks and loved the place! The view is breathtaking! Bed was very comfortable. In the villa we found everything for cooking, towels. The location is very convenient for visiting little towns ar  …see more

from £43 / night

£295 - £379 / week

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from £43 / night

7

Holiday apartment in Bettolle

Sinalunga / Bettolle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Ideally located between Montepulciano and Cortona in the small town of Bettolle, this holiday apartment is the perfect location to venture out and explore Tuscany.  …see more

from £59 / night

£337 / week

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from £59 / night

(1) Excellent 

35

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly
Il Noce is a very comfortable recently renovated apartment and is ideal for a quiet or active holiday in the idyllic countryside with splendid views and inviting walks. This attractive self contained apartment adjoins the main farmhouse where the owners live and has tw  …see more

from £85 / night

£589 / week

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from £85 / night

(1) Excellent 

46

Province of Siena / Siena

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 80 km
  • Child friendly

 …see more

from £177 / night

£1059 / week

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from £177 / night

20

Villa rental in Val d'Orcia with swimming pool

Montalcino / Val d'Orcia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Villa Bandini is located only 300 meters from the hamlet of Lucignano d’Asso on top of a hill on the border between the Val d’Orcia and the Sienese clay hills. Lucignano d’Asso is a medieval ancient hamlet which, since the XV century, has belonged to the Piccolomi  …see more

from £324 / night

£2265 - £3089 / week

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from £324 / night