Holiday Rentals in Province of Siena - Holiday Lettings - Villas

Close

View larger map

Also consider

Europe Holidays
451578 properties
Italy Holidays
103372 properties
Tuscany Holidays
23518 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
435 properties
Villas Siena
414 properties
Villas Montepulciano
315 properties
Casole d'Elsa
206 properties
Gaiole in Chianti
171 properties
Villas Castellina In Chianti
165 properties
Castelnuovo Berardenga
165 properties
Poggibonsi
164 properties
Villas Pienza
152 properties
Colle di Val d'Elsa
147 properties
Sinalunga
132 properties
Villas Montalcino
124 properties
Rapolano Terme
119 properties
Asciano
95 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

453 Holiday homes

Filters applied: House Parking Clear all

5

Home rental in Monteroni d'Arbia with swimming pool

Province of Siena / Monteroni d'Arbia

12 22 7 nights min

  • 12 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £456 / night

£3186 - £4779 / week

Book View

from £456 / night

(6) Very Good 

48

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
“A fabulous place to stay” The villa is well situated, within walking distance from the old town. It has beautiful views across the countryside. It was lovely to sit on the terrace in the cool as the sun was setting. We had a wonderful stay, as the vil
…see more

from £71 / night

£487 - £531 / week

Book View

from £71 / night

(12) Excellent 

Certificate of Excellence

26

Holiday home in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

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

Certificate of Excellence

from £71 / night

£553 - £755 / week

Book View

from £71 / night

5

Holiday home in Montisi

Province of Siena / Montisi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden

from £66 / night

£439 - £562 / week

Book View

from £66 / night

(3) Excellent 

25

Ski home to rent in Vivo d'Orcia

Province of Siena / Vivo d'Orcia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Ski
  • Child friendly

from £62 / night

£395 / week

Book View

Responds fast!
avg. 21 minutes

from £62 / night

(10) Excellent 

18

Colle di Val d'Elsa holiday home rental

Province of Siena / Colle di Val d'Elsa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 93 km
  • Child friendly
  • Pet friendly

from £62 / night

£351 - £600 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £62 / night

(2) Very Good 

35

Home rental in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 110 km
  • Child friendly
  • Air conditioning

from £133 / night

£753 - £877 / week

Book View

from £133 / night

(6) Very Good 

Certificate of Excellence

43

Montefienali holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £48 / night

£274 - £615 / week

Book View

Responds fast!
avg. 1 hour 43 minutes

from £48 / night

(6) Excellent 

31

Holiday home in Pianella

Castelnuovo Berardenga / Pianella

2 5 3 nights min

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

from £71 / night

£492 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from £71 / night

(2) Excellent 

16

Holiday home letting

Province of Siena / Monteriggioni

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £88 / night

£571 - £1150 / week

Book View

Responds fast!
avg. 3 hours 37 minutes

from £88 / night

(47) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £90 / night

£625 - £900 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from £90 / night

(1) Excellent 

26

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £82 / night

£571 - £1308 / week

Book View

from £82 / night

18

Montepulciano holiday home rental

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £85 / night

£540 - £647 / week

Book View

from £85 / night

23

Holiday home in Radicondoli

Province of Siena / Radicondoli

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 56 km
  • Swimming pool
  • Child friendly

from £314 / night

£2193 / week

Book View

from £314 / night

26

Holiday home with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £98 / night

£685 - £1312 / week

Enquire View

from £98 / night

(1) Excellent 

33

Holiday home rental

Province of Siena / Chiusdino

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly

from £176 / night

£1316 / week

Book View

from £176 / night

(1) Very Good 

30

Holiday home in Siena

Province of Siena / Siena

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden

from £58 / night

£395 - £457 / week

Book View

Responds fast!
avg. 3 hours 1 minutes

from £58 / night

42

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £290 / night

£1825 - £2812 / week

Book View

from £290 / night

(4) Excellent 

17

Holiday home in Cetona

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
“A real tase of Tuscany” If you're looking for an authentic old town stay then you'll be very happy. Great location in the old town and so close to lots small towns to explore. Train to Florence as a day trip. Large rooms cumfy beds and amazing views f
…see more

from £62 / night

£430 / week

Book View

from £62 / night

27

Radicondoli holiday home rental

Province of Siena / Radicondoli

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £84 / night

£571 - £1316 / week

Enquire View

from £84 / night

(1) Very Good 

15

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

from £67 / night

£425 - £788 / week

Book View

from £67 / night

(11) Excellent 

32

Home rental in Siena

Province of Siena / Siena

3 9 1 night min

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

from £351 / night

£1755 / week

Book View

Responds fast!
avg. 2 hours 55 minutes

from £351 / night

8

Monteriggioni holiday home rental

Province of Siena / Monteriggioni

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

Pricing unknown

Book View

Pricing unknown

(12) Excellent 

17

Siena holiday home rental

Province of Siena / Siena

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Nearest beach 95 km
  • Child friendly
  • Pet friendly
“What a wonderful stay! We highly recommend this house!” We instinctively felt in love with Leonardo's house the moment we arrived! The description we received from Leonardo how to get to the house was perfect and we immediately found the correct way
…see more

from £75 / night

£522 / week

Book View

from £75 / night

18

Holiday home in Castelnuovo dell'Abate

Montalcino / Castelnuovo dell'Abate

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 50 km
  • Child friendly

from £70 / night

£413 - £711 / week

Book View

from £70 / night

47

Home rental in San Gimignano

Province of Siena / San Gimignano

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

from £61 / night

£343 / week

Book View

from £61 / night

(1) Excellent 

30

San Gimignano holiday home rental

Province of Siena / San Gimignano

2 4 Min stay varies

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

from £53 / night

£360 - £834 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £53 / night

44

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £117 / night

£816 - £1215 / week

Book View

from £117 / night

(2) Very Good 

20

Pienza holiday home rental

Province of Siena / Pienza

2 4 2 nights min

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

from £89 / night

£531 - £903 / week

Book View

from £89 / night

35

Holiday home in Radicondoli

Province of Siena / Radicondoli

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets

from £132 / night

£615 / week

Book View

from £132 / night

24

Holiday home in Celle sul Rigo

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

from £71 / night

£308 / week

Book View

from £71 / night

14

Holiday home rental

Province of Siena / Cetona

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Suitable for children age 5+

Pricing unknown

Book View

Pricing unknown

4

Holiday home accommodation

Montepulciano / Gracciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 200 km
  • Child friendly
  • Ask about pets

Pricing unknown

Book View

Pricing unknown

16

Sant'Albino holiday home rental

Montepulciano / Sant'Albino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £71 / night

£439 - £623 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £71 / night

(2) Excellent 

32

Holiday home in Radicofani

Province of Siena / Radicofani

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool

from £53 / night

£351 - £588 / week

Book View

from £53 / night

(1) Excellent 

15

Pievescola holiday home rental

Province of Siena / Pievescola

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

from £88 / night

£615 / week

Book View

from £88 / night

(2) Excellent 

43

Radicondoli holiday home rental

Province of Siena / Radicondoli

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly

from £176 / night

£1106 / week

Book View

from £176 / night

38

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden

from £122 / night

£974 - £1531 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from £122 / night

4

Orgia holiday home rental

Province of Siena / Orgia

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Nearest beach 80 km
  • Private garden

from £15 / night

£103 / week

Book View

from £15 / night

18

Holiday home in Montepulciano

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £93 / night

£615 - £737 / week

Book View

from £93 / night

1