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Province of Siena

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1,424 Holiday homes

Filters applied: Pets allowed

Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“An awesome villa in the Tuscan hills” A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monterigg  …see more

from £128 / night

£848 - £1950 / week

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from £128 / night

(18) Excellent 

43

Holiday apartment in Monticchiello

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 consists of two bedrooms and two bathrooms with a fully equipped kitchen. The owners husband and wife Poli and Flora built the villa in 1988 and from there they guard with love the classic environment of the house.<br />Villa  …see more

from £64 / night

£314 - £765 / week

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from £64 / night

(3) Excellent 

26

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Ask about pets
“Excellent base for chilling and siteseeing/citytrips” We had a great time at Elena's place! The appartement was clean, big, safe and modern. We used our own kitchen to cook our food. We stayed a week longer then planned. It is a very good base to go b  …see more

from £77 / night

£306 - £475 / week

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from £77 / night

Featured properties

7

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

 …see more

from £68 / night

£467 - £704 / week

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from £68 / night

(6) Very Good 

40

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The  …see more

from £170 / night

£907 - £2289 / week

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from £170 / night

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very comfortable home away from home” Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun.  …see more

from £100 / night

£560 - £760 / week

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from £100 / night

(16) Excellent 

22

Casole d'Elsa holiday cottage rental

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
“Everything we wanted: excellent villa with lovely pool, beautiful countryside views and welcoming owners.” La Casa Dei Nonni was above and beyond our expectations. The location within the Tuscan hillside village of Monteguidi was easy to find from the  …see more

from £128 / night

£763 - £1145 / week

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from £128 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but  …see more

from £175 / night

£1100 - £1600 / week

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from £175 / night

(3) Excellent 

36

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets
Luxury villa made for 4 people is a rare find, and here you have it in abundance! Large 2-story building with 1 bedroom suite on each level, with living, dining and kitchen areas, covered terraces with views, and private pool in a well tended garden of herbs and roses.  …see more

from £194 / night

£1283 - £4267 / week

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from £194 / night

(11) Excellent 

21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Really worth staying!” My partner and I spent a glorious week this spring at agriturismo Il Salarco surrounded by vineyards and idyllic rolling countryside. The owner, an English lady called Laura, made us both feel really welcome, was fabulously know  …see more

from £68 / night

£373 - £1746 / week

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from £68 / night

(6) Excellent 

27

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets
Holiday in San Gimignano ... a journey into the heart of Tuscany.Dear Guests, we are the sisters Stefania and Margherita and we are the owners of Appartamento Margherita. We decided to rent the apartment where we were born about 15 years ago, when we underst  …see more

from £85 / night

£509 / week

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from £85 / night

20

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
On the ground floor of a 1600 Villa ,completely renovated for the maximum comfort of guests. All windows facing the valley and the natural reserve below.50 square meter private terrace with incredible view on the countryside.15x4 meter swimming pool .  …see more

Pricing unknown

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Pricing unknown

(33) Excellent 

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Great apartment. Fantastic Tuscan hospitality.” My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itse  …see more

from £85 / night

£467 - £721 / week

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from £85 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

from £480 / night

£3356 - £4450 / week

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from £480 / night

(2) Excellent 

19

Holiday apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning
Staying here will make your holiday unique: wake up in the shadow of the majestic Torre del Mangia is a feeling that isn't easily forgotten.I would like an unforgettable vacation, so I've taken care of all the details of the apartment where I want to welcome g  …see more

from £246 / night

£1611 - £2119 / week

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from £246 / night

(6) Excellent 

56

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning
The Villa and its gardens are a National Heritage property and there is a great deal to see and enjoy!  …see more

from £382 / night

£2331 / week

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from £382 / night

(10) Excellent 

10

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

 …see more

from £39 / night

£534 - £2225 / week

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from £39 / night

(9) Excellent 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £119 / night

£721 / week

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from £119 / night

(4) Excellent 

14

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 km
  • Child friendly
  • Ask about pets
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £85 / night

£467 - £721 / week

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from £85 / night

(2) Excellent 

16

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £246 / night

£1687 - £8899 / week

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from £246 / night

(4) Excellent 

53

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets
Casa Arianna self-cathering apartment in Montegabbro, a very little 12th century village in the hearth of Tuscany with Etruscan and Roman traces. Ideal for families seeking relaxation.<br />Private area outside to enjoy the quite of the village and the Tuscan coun  …see more

from £51 / night

£297 - £416 / week

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from £51 / night

(11) Excellent 

40

Holiday villa with swimming pool in San Giovanni d'Asso

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
3 BDR cosy house with small pool,AC,Wifi,patio; nestled in a village in Siena countryside. Private parking.<br />Please,ALWAYS enquiry about prices.  …see more

from £204 / night

£1424 - £1984 / week

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from £204 / night

(11) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple  …see more

from £60 / night

£450 - £801 / week

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from £60 / night

(2) Excellent 

40

Monticiano / Iesa Palazzo

6 9 1 night min

  • 6 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £153 / night

£1017 / week

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from £153 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a spectacular villa, immaculately furnished and presented in a wonderful part of Italy. The owners have imported furniture from around the world to create a unique setting for guests to enjoy their stay. Complete with private pool and beautiful gardens, it'  …see more

from £297 / night

£1653 - £3560 / week

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from £297 / night

(11) Excellent 

33

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
“Great stay!” Luca was wonderful to work with. He gave us directions on how to meet him and took us to the apartment to unload the car then helped us find a parking spot. Apartment was very nice, comfortable and close to the city center. Luca was alwa  …see more

from £77 / night

£441 - £536 / week

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from £77 / night

(10) Excellent 

58

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“unforgettable tuscan paradise” Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfa  …see more

from £567 / night

£3967 - £5170 / week

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from £567 / night

23

San Giovanni d'Asso holiday villa rental

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
Villa in the heart of Tuscany with private pool, stunning views!  …see more

from £170 / night

£1187 - £1780 / week

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from £170 / night

(12) Excellent 

49

Holiday villa in San Giovanni d'Asso

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
“Gorgeous villa in Tuscany” This is a gorgeous villa in the tuscan countryside. The villa was beautiful, spotless and had everything we needed. It is right next to the small town of San Giovanni D'Osso. My 16-year-old loved it as well. While we day-tri  …see more

from £460 / night

£3221 - £4153 / week

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from £460 / night

(21) Excellent 

43

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Perfect location with delightful owners” This is such a beautiful spot and ideal for exploring as very close to everything we wanted to see: Siena, San Gimignano, Volterra and many other less well known medieval towns and villages. The pool has a stu  …see more

from £85 / night

£467 - £721 / week

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from £85 / night

(1) Excellent 

26

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £79 / night

£551 - £1263 / week

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from £79 / night

(12) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
“Into the bliss!” The moment we arrived at the Autostazione di Montepulciano, Luca greeted us with a big smile and and an open heart that made this trip so particularly memorable. His flat on up on the edge of the hill was as described and better. It c  …see more

from £98 / night

£594 - £736 / week

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from £98 / night

(7) Excellent 

128

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Included: WIFI, electricity, water, gas for cooking use, weekly linen change, initial and final cleaning Heating on consumption.  …see more

from £636 / night

£2543 - £4211 / week

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from £636 / night

(3) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan apartment with shared swimming pool, not far from Siena. It sleeps up to 4 guests. It is an ideal place for families to spend a relaxing holiday far from town noises, among the peace of the countrside.<br />A heaven of peace in the heart of the M  …see more

from £77 / night

£509 - £933 / week

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from £77 / night

18

Province of Siena / Siena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £64 / night

£382 / week

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from £64 / night

20

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Elegant apartment in Villa near San Gimignano, pool, Chianti, wellness area, barbeque, garden, near restaurant, quiet location, Volterra, San Gimignano, Volterra,  …see more

from £98 / night

£695 / week

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from £98 / night

(9) Excellent 

18

Holiday farmhouse with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“peaceful paradise” This villa met all our expectations. The view from the bedrooms and the terrace were spectacular. Location in small village was perfect. Villa had special arragements for food delivery from local restaurants. Vila was spotless an  …see more

from £77 / night

£517 - £1017 / week

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from £77 / night

(1) Excellent 

20

Caprera holiday apartment rental

Siena / Caprera

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
Suite Le Camelie has all the comfort you would find in a hotel. It is at the same time a real Tuscany home with a local decor and feeling, surrounded by luxurius gardens and olive trees. Ideal location for visiting both Siena and the country side.  …see more

from £68 / night

£424 - £467 / week

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from £68 / 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

£255 / week

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from £39 / night

43

Holiday villa rental

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Treat yourself to the ideal 2-bedroom home for your dream vacation in Tuscany! La Casella is a luxurious private villa set on a gentle hillside with lush gardens and private pool, outside dining, views and close enough to walk into town. This well furnished villa is set  …see more

from £204 / night

£1348 - £3128 / week

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from £204 / night