Air conditioned apartments and villas to rent in Province of Siena

View larger map

Price per night

£366 Average

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Siena

Location

  • All locations
  • Asciano (20)
  • Bagno Vignoni (11)
  • Buonconvento (13)
  • Casciano (1)
  • Casole d'Elsa (9)
  • Castellina In Chianti (14)
  • Castelmuzio (2)
  • Castelnuovo Berardenga (37)
  • Castiglione D'Orcia (4)
  • Cetona (8)
  • Chianciano Terme (4)
  • Chiusdino (2)
  • Chiusi (7)
  • Colle di Val d'Elsa (13)
  • Gaiole in Chianti (52)
  • Le Piazze (2)
  • Montalcino (44)
  • Montecchio (1)
  • Montepulciano (52)
  • Monteriggioni (14)
  • Monteroni d'Arbia (15)
  • Monticiano (3)
  • Montisi (7)
  • Murlo (8)
  • Piancastagnaio (6)
  • Pienza (40)
  • Pievescola (1)
  • Poggibonsi (28)
  • Radda in Chianti (4)
  • Radicofani (8)
  • Radicondoli (1)
  • Rapolano Terme (22)
  • San Casciano dei Bagni (6)
  • San Gimignano (70)
  • San Giovanni d'Asso (22)
  • San Lorenzo a Merse (1)
  • San Quirico d'Orcia (2)
  • Sarteano (4)
  • Siena (176)
  • Sinalunga (14)
  • Sovicille (9)
  • Torrita di Siena (7)
  • Trequanda (5)
  • Ville di Corsano (2)

More

Less

Also consider

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
470 properties
Villas San Gimignano
409 properties
Villas Montepulciano
255 properties
Gaiole in Chianti
165 properties
Villas Casole d'Elsa
159 properties
Villas Castelnuovo Berardenga
154 properties
Villas Pienza
153 properties
Villas Poggibonsi
139 properties
Asciano
136 properties
Villas Sinalunga
130 properties
Villas Castellina In Chianti
129 properties
Villas Montalcino
125 properties
Apartments Colle di Val d'Elsa
122 properties
Villas Monteriggioni
93 properties
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

773 Holiday homes

Filters applied: Air conditioning (773)

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

1 / 5

Holiday apartment rental

Province of Siena / Pienza

2 5 1 night min stay

Apartment / 2 bedrooms / sleeps 5 / 1 night min stay

Add to shortlist

from £101 / night

£582 / week

Book

from £101 / night

(4) Very Good 

1 / 14

Poggibonsi holiday apartment rental

Province of Siena / Poggibonsi

1 3 Min stay varies

Apartment / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £47 / night

£326 - £466 / week

Book

from £47 / night

1 / 13

Monticchiello holiday villa let

Pienza / Monticchiello

2 5 1 night min stay

Villa / 2 bedrooms / sleeps 5 / 1 night min stay

Add to shortlist

from £117 / night

£659 / week

Book

from £117 / night

Featured properties

1 / 24

Holiday home in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min stay

House / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £63 / night

£272 / week

Book

from £63 / night

1 / 18

Ulignano holiday finca rental

San Gimignano / Ulignano

2 4 5 nights min stay

Finca / 2 bedrooms / sleeps 4 / 5 nights min stay

Add to shortlist

from £101 / night

£690 / week

Book

from £101 / night

1 / 18

Holiday apartment in Monteaperti

Castelnuovo Berardenga / Monteaperti

1 2 1 night min stay

Apartment / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £47 / night

£233 / week

Book

from £47 / night

(1) Very Good 

1 / 11

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 3 2 nights min stay

Apartment / 2 bedrooms / sleeps 3 / 2 nights min stay

Add to shortlist

from £55 / night

£326 / week

Book

from £55 / night

1 / 11

Holiday condo in San Gimignano

Province of Siena / San Gimignano

1 2 1 night min stay

Condo / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £63 / night

£435 / week

Book

from £63 / night

1 / 22

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min stay

Apartment / 2 bedrooms / sleeps 7 / 7 nights min stay

Add to shortlist

from £55 / night

£380 - £838 / week

Book

from £55 / night

1 / 21

Holiday farmhouse in Isola d'Arbia

Siena / Isola d'Arbia

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £60 / night

£418 - £1091 / week

Book

from £60 / night

1 / 12

Holiday farmhouse with shared pool in Isola d'Arbia

Siena / Isola d'Arbia

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £52 / night

£364 - £994 / week

Book

from £52 / night

1 / 11

Holiday home in Sovicille

Province of Siena / Sovicille

1 4 2 nights min stay

House / 1 bedroom / sleeps 4 / 2 nights min stay

Add to shortlist

from £43 / night

£287 - £365 / week

Book

from £43 / night

1 / 23

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 12 7 nights min stay

Villa / 6 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £493 / night

£3446 - £4543 / week

Book

from £493 / night

1 / 17

Holiday apartment in Torrita di Siena

Province of Siena / Torrita di Siena

2 4 4 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 4 nights min stay

Add to shortlist

from £125 / night

£774 / week

Book

from £125 / night

1 / 15

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

1 4 7 nights min stay

House / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £34 / night

£233 / week

Book

from £34 / night

1 / 13

Holiday villa in Monticchiello

Pienza / Monticchiello

2 2 7 nights min stay

Villa / 2 bedrooms / sleeps 2 / 7 nights min stay

Add to shortlist

from £78 / night

£543 / week

Book

from £78 / night

(1) Excellent 

1 / 19

Siena holiday apartment rental

Province of Siena / Siena

2 4 1 night min stay

Apartment / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £59 / night

£352 - £571 / week

Book

from £59 / night

1 / 21

Holiday apartment in Siena

Province of Siena / Siena

2 4 1 night min stay

Apartment / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £63 / night

£373 - £590 / week

Book

from £63 / night

1 / 28

Condo rental in Siena

Province of Siena / Siena

3 7 1 night min stay

Condo / 3 bedrooms / sleeps 7 / 1 night min stay

Add to shortlist

from £35 / night

£435 - £977 / week

Book

from £35 / night

1 / 29

Apartment letting in Siena

Province of Siena / Siena

1 2 3 nights min stay

Apartment / 1 bedroom / sleeps 2 / 3 nights min stay

Add to shortlist

from £82 / night

£407 / week

Book

from £82 / night

1 / 18

Holiday townhouse rental

Province of Siena / Cetona

2 7 3 nights min stay

Townhouse / 2 bedrooms / sleeps 7 / 3 nights min stay

Add to shortlist

from £55 / night

£427 / week

Book

from £55 / night

(1) Excellent 

1 / 18

Holiday apartment in Siena

Province of Siena / Siena

1 3 2 nights min stay

Apartment / 1 bedroom / sleeps 3 / 2 nights min stay

Add to shortlist

from £70 / night

£388 - £551 / week

Book

from £70 / night

1 / 24

Lodge rental in Abbadia di Montepulciano

Montepulciano / Abbadia di Montepulciano

8 7 1 night min stay

Lodge / 8 bedrooms / sleeps 7 / 1 night min stay

Add to shortlist

from £156 / night

£931 / week

Book

from £156 / night

1 / 7

Torrita di Siena ski b&b to rent.

Province of Siena / Torrita di Siena

1 4 1 night min stay

B&B / 1 bedroom / sleeps 4 / 1 night min stay

Add to shortlist

from £78 / night

£543 / week

Book

from £78 / night

1 / 13

Holiday apartment with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 3 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 3 nights min stay

Add to shortlist

from £78 / night

£427 / week

Book

from £78 / night

1 / 33

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

Apartment / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £83 / night

£576 - £880 / week

Book

from £83 / night

1 / 4

Holiday villa with swimming pool in Buonconvento

Province of Siena / Buonconvento

5 10 7 nights min stay

Villa / 5 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £286 / night

£2000 / week

Book

from £286 / night

1 / 24

Holiday castle accommodation

Gaiole in Chianti / Lecchi

6 14 7 nights min stay

Castle / 6 bedrooms / sleeps 14 / 7 nights min stay

Add to shortlist

from £373 / night

£2605 - £4008 / week

Book

from £373 / night

1 / 22

B&b rental in Pienza

Province of Siena / Pienza

3 2 1 night min stay

B&B / 3 bedrooms / sleeps 2 / 1 night min stay

Add to shortlist

from £82 / night

£489 / week

Book

from £82 / night

1 / 28

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 6 7 nights min stay

Villa / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £111 / night

£774 - £1500 / week

Book

from £111 / night

1 / 20

Monteriggioni holiday apartment rental

Province of Siena / Monteriggioni

1 2 7 nights min stay

Apartment / 1 bedroom / sleeps 2 / 7 nights min stay

Add to shortlist

from £34 / night

£233 - £311 / week

Book

from £34 / night

1 / 25

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

2 7 Min stay varies

Apartment / 2 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £71 / night

£493 - £885 / week

Book

from £71 / night

1 / 19

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

5 10 7 nights min stay

Villa / 5 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £538 / night

£3764 - £3973 / week

Book

from £538 / night

1 / 25

Holiday apartment with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 3 Min stay varies

Apartment / 2 bedrooms / sleeps 3 / Min stay varies

Add to shortlist

from £71 / night

£493 - £799 / week

Book

from £71 / night

1 / 23

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

Apartment / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £59 / night

£109 - £435 / week

Book

from £59 / night

1 / 9

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £42 / night

£288 - £478 / week

Book

from £42 / night

1 / 23

Holiday villa with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £92 / night

£640 - £1663 / week

Book

from £92 / night

1 / 11

B&b rental in Serre di Rapolano

Rapolano Terme / Serre di Rapolano

1 1 Min stay varies

B&B / 1 bedroom / sleeps 1 / Min stay varies

Add to shortlist

from £32 / night

£218 / week

Book

from £32 / night

1 / 8

Holiday b&b letting

Province of Siena / Siena

1 2 1 night min stay

B&B / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £70 / night

£466 / week

Book

from £70 / night

1 / 14

Holiday apartment in Pianella

Castelnuovo Berardenga / Pianella

1 2 1 night min stay

Apartment / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £32 / night

£202 / week

Book

from £32 / night

1 / 15

Holiday apartment rental

Siena / Isola d'Arbia

1 4 7 nights min stay

Apartment / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £60 / night

£415 / week

Book

from £60 / night

(2) Excellent 

1 / 20

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £54 / night

£373 - £814 / week

Book

from £54 / night

(10) Excellent 

1 / 21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

Cottage / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £63 / night

£357 - £1597 / week

Book

from £63 / night

1 / 13

Home rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 6 Min stay varies

House / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £108 / night

£750 - £950 / week

Book

from £108 / night

(1) Very Good 

1 / 22

B&b rental in Pienza

Province of Siena / Pienza

5 12 Min stay varies

B&B / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £63 / night

£427 / week

Book

from £63 / night

1 / 45

Holiday b&b with shared pool in Montepulciano

Province of Siena / Montepulciano

4 12 Min stay varies

B&B / 4 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £559 / night

£2132 / week

Book

from £559 / night

(2) Excellent 

1 / 14

Monteriggioni holiday b&b rental

Province of Siena / Monteriggioni

2 4 Min stay varies

B&B / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £94 / night

£597 / week

Book

from £94 / night

1 / 23

Home rental in San Gimignano with shared pool

Province of Siena / San Gimignano

1 4 1 night min stay

House / 1 bedroom / sleeps 4 / 1 night min stay

Add to shortlist

from £83 / night

£698 / week

Book

from £83 / night

1 / 15

Holiday cottage with golf nearby in Sinalunga

Province of Siena / Sinalunga

1 4 Min stay varies

Cottage / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £70 / night

£400 / week

Book

from £70 / night

1 / 28

Apartment rental in Siena

Province of Siena / Siena

2 5 1 night min stay

Apartment / 2 bedrooms / sleeps 5 / 1 night min stay

Add to shortlist

from £77 / night

£737 - £1144 / week

Book

from £77 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page