Air conditioned apartments and villas to rent in Province of Siena

Close

View larger map

Also consider

Europe Holidays
430930 properties
Italy Holidays
101106 properties
Tuscany Holidays
24779 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 San Gimignano
506 properties
Villas Siena
451 properties
Villas Montepulciano
302 properties
Casole d'Elsa
217 properties
Colle di Val d'Elsa
207 properties
Castelnuovo Berardenga
202 properties
Poggibonsi
181 properties
Villas Castellina In Chianti
170 properties
Villas Montalcino
156 properties
Gaiole in Chianti
156 properties
Villas Pienza
151 properties
Rapolano Terme
150 properties
Sinalunga
148 properties
Asciano
126 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

907 Holiday homes

Filters applied: Air conditioning

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

(2) Excellent 

12

Rapolano Terme / Serre di Rapolano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 110 km
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£339 - £517 / week

Book View

from £60 / night

7

Province of Siena / Colle di Val d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

(6) Excellent 

37

Torrita di Siena / Montefollonico

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £102 / night

£1102 - £1992 / week

Book View

from £102 / night

Featured properties

(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) Average 

25

Province of Siena / San Quirico d'Orcia

1 2 Min stay varies

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

 …see more

from £102 / night

£712 / week

Book View

from £102 / night

(6) Very Good 

24

Farmhouse rental in Caprera

Siena / Caprera

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
Elegant Liberty farmhouse on the hills, in a quite village just ten minutes from Siena city centre. Stunning view toward the city steeples across the countryside. Olive groves and fields for walking and horse riding. Garden and farm yard for outdoor dining.  …see more

from £162 / night

£1060 / week

Book View

from £162 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

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
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany.<b  …see more

from £44 / night

£306 - £365 / week

Enquire View

from £44 / night

(1) Excellent 

24

Holiday villa with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa with pool in Chianti is located near the town of Poggibonsi, surrounded by the gently rolling hills of this beautiful region. The accommodation is on two floors and can comfortably accommodate up to 18 people. Accommodation, 400 sqm : GROUND FLOOR  …see more

from £234 / night

£1636 - £3941 / week

Book View

from £234 / night

15

Holiday apartment in Larniano

San Gimignano / Larniano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
Lovely Two-roomed apartment (55 mq), 2-4 beds, inside San Gimignano. In a central position, but also surrounded by a rare and precious silence, our apartments offer the unique feeling of an ancient building with all the comfort of modern amenities.<br />Car parkin  …see more

from £76 / night

£526 / week

Book View

from £76 / 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 £243 / night

£1695 - £5806 / week

Book View

from £243 / night

(1) Very Good 

21

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Air conditioning

 …see more

from £135 / night

£944 / week

Book View

from £135 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
“Well-located and roomy house” We were 10 adults and two children (three generations) spending one week at the house in May of 2014. We found the house very suitable (for five couples) since it had five large bedrooms. It was very convenient that each  …see more

from £231 / night

£1611 - £2882 / week

Book View

from £231 / night

(9) Excellent 

57

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £217 / night

£1513 - £2759 / week

Book View

from £217 / night

18

B&b letting in Monticchiello

Pienza / Monticchiello

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Air conditioning
Antica Locanda PienzaAntica Locanda Pienza  …see more

from £73 / night

£467 / week

Book View

from £73 / 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 sunflo  …see more

from £628 / night

£3645 - £4916 / week

Book View

from £628 / night

14

Province of Siena / Casole d'Elsa

1 4 Min stay varies

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

 …see more

from £74 / night

£450 - £823 / week

Book View

from £74 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

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
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri  …see more

from £276 / night

£1933 - £2492 / week

Book View

from £276 / night

7

Province of Siena / Casole d'Elsa

1 4 Min stay varies

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

 …see more

from £74 / night

£450 - £823 / week

Book View

from £74 / 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 £458 / night

£2543 - £3390 / week

Book View

from £458 / night

(1) Excellent 

27

Holiday farmhouse rental

Province of Siena / San Gimignano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats communicating inside in old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedro  …see more

from £111 / night

£746 - £1356 / week

Book View

from £111 / night

18

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary
Brown apartment Central and cosy apartment with double bedroom, bathroom with shower, large living area with sofa bed, equipped kitchen, private equipped garden, free WIFI, TV, air conditioning.<br />Upon request as extra services: cooking classes, wine tours, e  …see more

from £51 / night

£356 / week

Book View

from £51 / night

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

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

£297 / week

Book View

from £68 / night

(2) Excellent 

25

Province of Siena / Montepulciano

2 4 3 nights min

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

 …see more

from £119 / night

£763 / week

Book View

from £119 / 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 £246 / night

£1356 - £1950 / week

Book View

from £246 / 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.<br />Upon request as extra servic  …see more

from £43 / night

£297 / week

Book View

from £43 / night

100

Holiday apartment with shared pool in Bagno Vignoni

Province of Siena / Bagno Vignoni

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

Pricing unknown

Enquire View

Pricing unknown

(14) Excellent 

17

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
“Great Tuscan apartment... but not for summer heat.” My husband and I had originally hoped to stay in Il Duca for 2 months, but because of the heat in Tuscany this summer, we had to seek other accommodations with air conditioning. Pros: The apartme  …see more

from £88 / night

£611 / week

Book View

from £88 / night

16

Contignano holiday villa rental

Radicofani / Contignano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

Pricing unknown

Enquire View

Pricing unknown

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

5

Province of Siena / Rapolano Terme

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £77 / night

£534 - £594 / week

Book View

from £77 / night

(3) 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
The property PODERE SORTOIANO dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments, as well as the "hut" were once stables for livestock. It has now been restored by the Santini family with much  …see more

from £47 / night

£314 - £373 / week

Book View

from £47 / 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 £450 / night

£2712 - £3780 / week

Book View

from £450 / night

17

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights 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. l  …see more

from £111 / night

£670 / week

Book View

from £111 / night

27

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £1022 / night

£7149 / week

Book View

from £1022 / night

24

Province of Siena / San Quirico d'Orcia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £119 / night

£831 / week

Book View

from £119 / night

25

Casole d'Elsa holiday apartment rental

Province of Siena / Casole d'Elsa

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
This elegant and modern 2 bedroom, 2 bathroom ground floor apartment is furnished to high standards and is very well kept. It is provided with independent central heating and air conditioning. The living room contains 2 comfortable sofas, shelf unit hosting a satellite  …see more

from £90 / night

£628 - £1051 / week

Enquire View

from £90 / 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 £467 / night

£2712 - £5255 / week

Book View

from £467 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 2 nights min

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

 …see more

from £162 / night

£1128 / week

Book View

from £162 / night

(1) Very Good 

19

Holiday apartment in Radicofani

Province of Siena / Radicofani

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
The apartment can host 4 to 6 people and is constituted by a double bedroom with bathroom, a loft with a queen bed of 120 cm and a bathroom, a large living room with equipped cooking area and a sofa bed which can sleep three people. The apartment is equipped with any co  …see more

from £84 / night

£323 - £797 / week

Book View

from £84 / night