Air conditioned apartments and villas to rent in Province of Siena

Close

View larger map

Also consider

Europe Holidays
419302 properties
Italy Holidays
101462 properties
Tuscany Holidays
24841 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas Siena
481 properties
Villas San Gimignano
473 properties
Villas Montepulciano
288 properties
Castelnuovo Berardenga
208 properties
Colle di Val d'Elsa
184 properties
Casole d'Elsa
176 properties
Gaiole in Chianti
168 properties
Poggibonsi
164 properties
Villas Montalcino
155 properties
Villas Castellina In Chianti
155 properties
Villas Pienza
148 properties
Sinalunga
142 properties
Rapolano Terme
130 properties
Asciano
119 properties

Province of Siena

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

872 Holiday homes

Filters applied: Air conditioning (874)

(2) Very Good 

20

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

from £58 / night

£407 - £801 / week

Book View

from £58 / night

(2) Excellent 

11

Siena holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
A spacious and luminous two roomed unit (55sqm) in Siena that can accommodate up to 4 guests; just 2 km outside the ancient walls of the historical centre of Siena. Private parking.  …see more

from £94 / night

£628 - £797 / week

Book View

from £94 / night

(1) Average 

10

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £85 / night

£382 / week

Book View

from £85 / night

(5) Excellent 

15

Poggibonsi / Staggia Senese

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £77 / night

£534 / week

Book View

from £77 / night

100

Montalcino holiday villa rental

Province of Siena / Montalcino

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a stunning villa set in Tuscany Italy. It has 4 bedrooms and 3 bathrooms, and it is ideal for those who are looking for a memorable experience. This property features: a swimming Pool, air Conditioning .  …see more

from £237 / night

£1656 - £2718 / week

Enquire View

from £237 / night

23

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
An ancient farmhouse dating back to 1846 that lies in an agricultural farm that extends over a surface of 150 hectares. Every year our olive grove produces a tasty oil that can be tasted and purchased during your stay.  …see more

from £520 / night

£3636 - £4975 / week

Book View

from £520 / night

(1) Excellent 

30

San Gimignano / Santa Maria, San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £68 / night

£441 - £530 / week

Book View

from £68 / night

19

Holiday cottage with swimming pool in Cetona

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Pretty, restored cottage with swimming pool and bowling alley.  …see more

from £319 / night

£2229 - £3272 / week

Enquire View

from £319 / night

4

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Large apartment at the ground floor of the villa.Vaulted ceilings, large rooms, all comforts. Large master bedroom om with king size bed, living room with two beds, large dining and cooking room, bathroom with shower.The area is famous for the Dante Alig  …see more

from £128 / night

£678 - £1017 / week

Book View

from £128 / night

(4) Very Good 

14

Apartment rental in Siena

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
“nice stay, central, clean” property was as advertised, very clean, easy access, central and very near to the central bus stop, owner came to pick us up at the bus station, we were very happy with our choice  …see more

from £42 / night

£291 / week

Book View

from £42 / night

20

Holiday home in Buonconvento

Province of Siena / Buonconvento

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

from £947 / night

£3786 - £6121 / week

Enquire View

from £947 / night

34

Sant'Albino holiday villa rental

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano are amo  …see more

from £364 / night

£2543 - £5255 / week

Enquire View

from £364 / night

(6) Excellent 

19

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Count Filippo Fiorentini will host you in his residence near the village of Monteroni d'Arbia, at only 7 miles from Siena, in the gorgeous farm estate of San Fabiano, once owned by the Late Count Fiorentini, with a XII century castle, beautiful fields of sunflowers,  …see more

from £628 / night

£3645 - £4916 / week

Book View

from £628 / night

(1) Average 

7

Siena holiday apartment rental

Province of Siena / Siena

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
There is a shopping area 500 meters away from the apartment: 3 supermarkets, shops, coffee, bar, bakery..  …see more

from £85 / night

£568 - £763 / week

Book View

from £85 / night

(1) Very Good 

11

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
Large outdoor area.Homely and friendly atmosphere.The tranquility of the countryside just a few steps away from the center.  …see more

from £60 / night

£356 / week

Book View

from £60 / 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

Book View

from £460 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £106 / night

£653 - £975 / week

Book View

from £106 / 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

Book View

Pricing unknown

15

B&b rental in Serre di Rapolano

Rapolano Terme / Serre di Rapolano

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
Poppy bedroom: single bed, private bathroom with shower, toilet, hairdryer, courtesy set, WiFi, Tv in room upon request, air conditioning. A stay at Antico Granaione b&b will delight You with unique and moving experiences.  …see more

from £34 / night

£238 / week

Book View

from £34 / night

20

Sovicille holiday b&b let

Province of Siena / Sovicille

3 3 2 nights min

  • 3 bedrooms
  • Sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
ROOMSBeautiful rooms, elegantly furnished, spacious and comfortable, with large windows which overlook the beautiful landscapes of the historic city of Siena and the green of uncontaminated nature.Each is equipped with air conditioning and a private bathroom.  …see more

from £111 / night

£695 / week

Book View

from £111 / night

15

Sarteano holiday villa rental

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 120 km
  • Child friendly
  • Air conditioning
The home is part of a two family Villa located in a spacious garden near Sarteano, in the heart of Tuscany. The home has 4 bedrooms and offers hospitality to up to 8 guests. The house is fully equipped for a pleasant country retreat, with a fully equipped kitchen to ex  …see more

from £79 / night

£551 - £1433 / week

Book View

from £79 / 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 £242 / night

£1695 - £3814 / week

Book View

from £242 / night

(2) Excellent 

12

Farmhouse rental in Val di Merse

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
For couple, family or group of friends that want to taste the Tuscan countryside with small budget. The property is close to Siena, San Gimignano, Monteriggioni and others famous places !Country house , 1 room, kitchen , 1 bathroom with private terrace and garden .REED  …see more

from £40 / night

£250 - £370 / week

Book View

from £40 / night

(1) Excellent 

21

Province of Siena / Cetona

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Child friendly

 …see more

from £178 / night

£1246 / week

Book View

from £178 / night

24

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning

 …see more

from £62 / night

£331 / week

Book View

from £62 / 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 £111 / night

£594 / week

Book View

from £111 / 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 £165 / night

£1000 - £1600 / week

Enquire View

from £165 / night

(2) Excellent 

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa in Siena with SPA room and swimming pool at exclusive use.  …see more

from £231 / night

£1611 - £3389 / week

Book View

from £231 / night

(1) Excellent 

23

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Great place for family and friends” We rented all three cottages for a group of 17 including small children and adults. We couldn't have asked for a better vacation. The area is beautiful, serene and relaxing. Having the pool there took the pressur  …see more

from £140 / night

£1102 / week

Book View

from £140 / night

(1) Very Good 

39

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £102 / night

£594 - £742 / week

Book View

from £102 / night

(1) Excellent 

11

Holiday apartment accommodation

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Siena apartment with easy access to the town centre  …see more

from £60 / night

£373 - £467 / week

Book View

from £60 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £229 / night

£1272 - £1865 / week

Book View

from £229 / night

16

Holiday villa with shared pool in Val d'Orcia

Montalcino / Val d'Orcia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful newly restored two bedroom house with large kitchen, living room, garden and a swimming pool. Incredible unbroken 360 views over the Val D'Orcia valley. Sun-baked stone walls hand made terracotta floors, chestnut beams, pergolas twisted with wisteria.Loca  …see more

from £73 / night

£509 - £589 / week

Enquire View

from £73 / night

34

Holiday villa in Montepulciano

Province of Siena / Montepulciano

7 19 Min stay varies

  • 7 bedrooms
  • Sleeps 19
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Podere Monti is a 16th century farmhouse nestled between woods and olive groves. It has been turned into a residence of refined charm that retains its atmosphere of informal welcome. The guest rooms are few but exquisitely furnished; each one has its own unique charac  …see more

from £463 / night

£2690 - £5211 / week

Book View

from £463 / night

100

Larniano holiday villa rental

San Gimignano / Larniano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this vacation villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

from £330 / night

£1907 - £3178 / week

Enquire View

from £330 / night

27

Montepulciano holiday villa rental

Province of Siena / Montepulciano

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte pover  …see more

from £545 / night

£3814 - £6645 / week

Book View

from £545 / night

(1) Excellent 

12

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Green apartment Siena centre-Central, ground floor, easy accessible, cosy, tastefully furnished. Double bedroom, fully equipped kitchen with sofa bed for two guests, large bathroom with shower, free WIFI, sat Tv, air conditioning.Upon request as extra services: cooking  …see more

from £38 / night

£262 / week

Book View

from £38 / 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

Book View

from £246 / night

(2) Very Good 

100

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more

from £334 / night

£1949 - £2918 / week

Enquire View

from £334 / night

19

Holiday apartment in Casaglia

San Gimignano / Casaglia

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the elegantly renovated barn, Iris is particularly spacious and filled with natural light.Baby bed on request is free  …see more

from £127 / night

£816 - £1120 / week

Book View

from £127 / night