Air conditioned apartments and villas to rent in Province of Siena

Close

View larger map

Also consider

Europe Holidays
430282 properties
Italy Holidays
102686 properties
Tuscany Holidays
25799 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
495 properties
Villas Siena
461 properties
Villas Montepulciano
308 properties
Castelnuovo Berardenga
210 properties
Colle di Val d'Elsa
205 properties
Casole d'Elsa
202 properties
Poggibonsi
176 properties
Villas Castellina In Chianti
171 properties
Gaiole in Chianti
170 properties
Villas Montalcino
165 properties
Villas Pienza
158 properties
Sinalunga
152 properties
Rapolano Terme
145 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

930 Holiday homes

Filters applied: Air conditioning (965)

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

18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in g  …see more

from £70 / night

£351 / week

Book View

from £70 / 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 £62 / night

£386 - £483 / week

Book View

from £62 / night

(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 £91 / night

£632 / week

Book View

from £91 / night

(6) Excellent 

20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Comfortable new apartment in a traditional style, highly recommended.” The apartment has a lovely view over the town and the hills beyond. It's an easy walk down into the town centre which has bars, restaurants and a pizza cafe, though it's uphill (an  …see more

from £65 / night

£400 - £800 / week

Book View

from £65 / night

20

Siena holiday villa accommodation

Province of Siena / Siena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Villa Le Cantine di Cerreto is one of our best villas in Italy for rent. Immersed in the heart of the countryside with beautiful swimming pool, this spectacular villa can comfortably sleep up to 14 people and is ideal for your vacation rental in Italy.  …see more

from £2014 / night

£14098 / week

Enquire View

from £2014 / 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 £497 / night

£3474 - £4606 / week

Enquire View

from £497 / night

20

Sarteano holiday manor house rental

Province of Siena / Sarteano

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful stone manor house with heated swimming pool and outdoor heated jacuzzi.  …see more

from £980 / night

£6860 - £16448 / week

Enquire View

from £980 / 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 £123 / night

£860 / week

Book View

from £123 / night

(3) Excellent 

18

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjo  …see more

Pricing unknown

Book View

Pricing unknown

22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Nr. San Gimignano, Siena Province, Tuscany, Italy Typical Tuscan Style Villa with Private Pool and Large Private garden. 12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive Grove Wonderful stone building situated in a peaceful position wit  …see more

from £141 / night

£1536 - £2632 / week

Book View

from £141 / night

5

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Il Pino apartment is located in the villa Podernovo at San Fabiano farmestate. It offers stunning views on the Arbia valleys and the skyline of Montalcino, and an authenitc athmosphere of a Tuscan home.The furnitures ,the air conditioning, the TV satellite with Sky  …see more

from £115 / night

£658 - £878 / week

Book View

from £115 / 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 £239 / night

£1667 - £2983 / week

Book View

from £239 / night

(1) Excellent 

13

Province of Siena / Asciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £97 / night

£658 - £843 / week

Book View

from £97 / night

20

Province of Siena / Monteriggioni

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning

 …see more

from £38 / night

£264 / week

Book View

from £38 / night

4

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning and heated swimming pool. The apartment Il Forno is at first floor of the villa, with a master bedroom with king size bed,  …see more

from £115 / night

£658 - £878 / week

Book View

from £115 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Originally a country estate dating back to 1795, this superb Leopoldine villa blends outstanding elegance and comfort with traditional rustic features which reflect its long history. It retains the typical rooftop pigeon-loft, now romantically transformed into an extra-  …see more

from £1076 / night

£6031 - £7128 / week

Enquire View

from £1076 / 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 £224 / night

£1566 - £2856 / week

Book View

from £224 / 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 £87 / night

£334 - £825 / week

Book View

from £87 / night

32

Holiday villa rental

Province of Siena / Trequanda

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £500 / night

£3500 / week

Book View

from £500 / night

14

Casole d'Elsa holiday apartment rental

Casole d'Elsa / Monteguidi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
This charming farmhouse complex is the result of a recent and elegant restoration of a typical Tuscan country complex, near the town of Casole d'Elsa, in the province of Siena. The Etruscan hills surrounding the property are but a short distance from the most celeb  …see more

from £89 / night

£623 - £992 / week

Enquire View

from £89 / night

(1) Excellent 

18

Province of Siena / Siena

1 3 2 nights min

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

 …see more

from £79 / night

£483 - £667 / week

Book View

from £79 / 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 £650 / night

£3772 - £5088 / week

Book View

from £650 / night

52

Holiday villa rental

Poggibonsi / Staggia Senese

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Villa Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence. Villa Senese is an holiday villa in Tuscany, located in a vantage position on a hill above the old town  …see more

from £527 / night

£3685 - £4913 / week

Enquire View

from £527 / night

(1) Excellent 

37

Holiday lodge with shared pool in Pienza

Province of Siena / Pienza

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 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 £119 / night

£829 - £1443 / week

Book View

from £119 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Centrum of city only 15 minutes by foot ! The villa was perfectly clean when we arrived. The kitchen is well equipped and fun to cook in.We highly recommend this property for those who are looking for a peaceful setting near all that Siena has to offer.  …see more

from £259 / night

£1097 - £2325 / week

Book View

from £259 / night

(1) Excellent 

19

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an 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 bedroom and a dinin  …see more

from £59 / night

£404 - £729 / week

Book View

from £59 / night

(4) Excellent 

19

Siena holiday apartment rental

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Appartamento bello ed elegante appena ristrutturato ed arredato di nuovo, vicino al centro storico della città. Nella zona notte soffitti con travi a vista, nella tipica tradizione toscana. Composto da ampia cucina/soggiorno, camera matrimoniale, camera di passag  …see more

from £71 / night

£439 - £685 / week

Book View

from £71 / night

(1) Excellent 

32

Holiday home in Le Piazze

Province of Siena / Le Piazze

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The nature of the Val di Chiana, where the village is situated, is gorgeous.  …see more

from £43 / night

£264 - £386 / week

Book View

from £43 / night

26

Villa rental in Sant'Albino with swimming pool

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £264 / night

£1843 - £3158 / week

Enquire View

from £264 / 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 £77 / night

£465 - £851 / week

Book View

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 £586 / night

£4106 - £5351 / week

Book View

from £586 / night

27

Apartment rental in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 96 km
  • Suitable for children age 5+
  • Car not necessary
This cosy, typical Sienese two bedroom apartment for 2 to 4 people is located in the historic city center of Siena approx. 300 meters distant from „Piazza del Campo“. All the main attractions of the historic centre are within walking distance. Public parkin  …see more

from £84 / night

£584 - £805 / week

Book View

from £84 / night

20

Villa rental in Castiglione D'Orcia with swimming pool

Province of Siena / Castiglione D'Orcia

1 21 7 nights min

  • 1 bedroom
  • Sleeps 21
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Farmhouse divided into apartments set in 10 hectares of private forest and with a large swimming pool.<br />sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

from £633 / night

£4430 - £6356 / week

Enquire View

from £633 / 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 £167 / night

£1097 / week

Book View

from £167 / night

(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 £106 / night

£1141 - £2062 / week

Book View

from £106 / night

(2) Very Good 

19

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Air conditioning
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite i  …see more

from £145 / night

£1014 / week

Book View

from £145 / night

(1) Excellent 

13

Holiday villa with shared pool, golf nearby in Sovicille

Province of Siena / Sovicille

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 68 km
  • Swimming pool
  • Air conditioning
The holiday home "Il Rifugio del Falconiere" offers an elegant villa of 220 square meters with a large living room, where there is a fireplace and a unique décor, a large dining room, a fully equipped kitchen with dishwasher, refrigerator that produces  …see more

from £439 / night

£3071 / week

Book View

from £439 / night

(6) Excellent 

21

Villa rental in Montisi with swimming pool

Province of Siena / Montisi

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A beautifully restored fully air-conditioned 16th century village house, filled with antiques. There are 4 bedroom/5 bath with stunning views, a garden overlooking the stunning Tuscan countryside, and a pool. Groceries, gelato and the best coffee within yards - and a fu  …see more

from £260 / night

£1650 - £2890 / week

Book View

from £260 / night

(3) Very Good 

35

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £93 / night

£645 / week

Book View

from £93 / 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 £245 / night

£1714 - £2814 / week

Enquire View

from £245 / night