Air conditioned apartments and villas to rent in Province of Siena

Close

View larger map

Also consider

Europe Holidays
427807 properties
Italy Holidays
99152 properties
Tuscany Holidays
22167 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
445 properties
Villas Siena
414 properties
Villas Montepulciano
275 properties
Castelnuovo Berardenga
183 properties
Casole d'Elsa
174 properties
Gaiole in Chianti
163 properties
Colle di Val d'Elsa
151 properties
Poggibonsi
137 properties
Villas Pienza
136 properties
Villas Castellina In Chianti
136 properties
Rapolano Terme
116 properties
Villas Montalcino
113 properties
Sinalunga
113 properties
Asciano
93 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

800 Holiday homes

Filters applied: Air conditioning

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning

from £72 / night

£500 - £795 / week

Book View

from £72 / 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

from £194 / night

£1356 - £3389 / week

Book View

from £194 / 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

from £106 / night

£653 - £975 / week

Book View

from £106 / 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

from £246 / night

£1356 - £1950 / week

Book View

from £246 / 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

from £248 / night

£1051 - £2227 / week

Book View

from £248 / night

(3) Very Good 

28

Province of Siena / Castelnuovo Berardenga

2 4 2 nights min

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

from £59 / night

£410 / week

Book View

from £59 / 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

from £314 / night

£1992 - £8899 / week

Book View

from £314 / night

(23) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

from £47 / night

£284 - £412 / week

Book View

from £47 / night

16

Contignano holiday villa rental

Radicofani / Contignano

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Pricing unknown

Enquire View

Pricing unknown

(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

from £42 / night

£253 - £412 / week

Book View

from £42 / 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

from £135 / night

£944 / week

Book View

from £135 / night

(4) 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

from £68 / night

£382 - £848 / week

Book View

from £68 / night

(2) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien
…see more

from £128 / night

£1000 - £2204 / week

Book View

from £128 / 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

from £234 / night

£1636 - £3941 / week

Book View

from £234 / night

(5) Excellent 

46

Holiday farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £206 / night

£1441 / week

Book View

from £206 / night

(11) Excellent 

26

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £68 / night

£522 - £723 / week

Book View

from £68 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children age 5+

from £60 / night

£416 - £862 / week

Enquire View

from £60 / night

22

Province of Siena / Pienza

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £89 / night

£534 / week

Book View

from £89 / 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

from £51 / night

£353 / week

Book View

from £51 / night

16

Siena / Sant Andrea a Montecchio

1 2 Min stay varies

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

from £59 / night

£412 / week

Book View

from £59 / 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

from £215 / night

£1500 - £2736 / week

Book View

from £215 / night

19

Province of Siena / Siena

1 3 2 nights min

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

from £76 / night

£463 - £639 / week

Book View

from £76 / night

31

Murlo / Casciano di Murlo

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £68 / night

£411 - £487 / week

Book View

from £68 / night

(46) Excellent 

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Perfection in rural Tuscany” From the outset we knew that this place would be special. From reviewing the property on TripAdvisor, looking at the pictures, reading other travellers reviews right through to the wonderful prompt and attentive service r
…see more

from £90 / night

£625 - £900 / week

Book View

from £90 / 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

from £74 / night

£450 - £823 / week

Book View

from £74 / night

(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

from £68 / night

£428 - £801 / week

Book View

from £68 / night

6

Holiday villa in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £170 / night

£1102 - £1526 / week

Book View

from £170 / 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

from £76 / night

£526 / week

Book View

from £76 / 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

from £34 / night

£238 / week

Book View

from £34 / night

(1) Very Good 

10

Holiday apartment in Siena

Province of Siena / Siena

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

from £111 / night

£755 - £1017 / week

Book View

from £111 / night

(1) Excellent 

22

Holiday apartment in Tognazza

Province of Siena / Tognazza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
“Great location to explore Tuscany from.” Lovely apartment with everything you need to be comfortable. Location was great for exploring Tuscany. Saverio (host) was also very helpful. Would recommend highly.
…see more

from £26 / night

£177 / week

Book View

from £26 / night

16

Province of Siena / Castellina In Chianti

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Pricing unknown

Book View

Pricing unknown

(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

from £47 / night

£311 - £370 / week

Book View

from £47 / night

5

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £111 / night

£594 / week

Book View

from £111 / 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

from £68 / night

£421 - £656 / week

Book View

from £68 / night

(12) Excellent 

50

Holiday villa with indoor pool, golf nearby in Gaiole in Chianti

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £687 / night

£4806 - £7089 / week

Book View

from £687 / night

(8) Excellent 

32

Province of Siena / Siena

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £339 / night

£1695 / week

Book View

from £339 / night

5

Montepulciano holiday farmhouse rental

Province of Siena / Montepulciano

1 2 1 night min

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

from £102 / night

£712 / week

Book View

from £102 / 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

from £84 / night

£323 / week

Book View

from £84 / night

(2) Excellent 

17

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £94 / night

£534 - £979 / week

Book View

from £94 / night

1