Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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Province of Siena

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5,782 Holiday homes

22

Holiday apartment with swimming pool in Crete Senesi

Asciano / Crete Senesi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £105 / night

£734 / week

Book View

from £105 / night

(13) Excellent 

Certificate of Excellence

17

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £64 / night

£796 / week

Book View

from £64 / night

(1) Excellent 

13

Holiday b&b in Montepulciano

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly

from £75 / night

£437 / week

Book View

from £75 / night

(2) Very Good 

12

Holiday condo in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary

from £62 / night

£428 / week

Book View

Responds fast!
avg. 41 minutes

from £62 / night

14

Holiday apartment with shared pool in Pievescola

Province of Siena / Pievescola

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children age 5+

from £62 / night

£393 / week

Book View

from £62 / night

(6) Excellent 

16

Farmhouse rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £219 / night

£1,529 / week

Book View

from £219 / night

(6) Very Good 

56

Holiday apartment rental

Torrita di Siena / Montefollonico

2 4 2 nights min

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

from £166 / night

£1,161 / week

Book View

from £166 / night

14

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly

from £62 / night

£350 / week

Book View

from £62 / night

(12) Very Good 

Certificate of Excellence

16

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 105 km
  • Swimming pool
  • Car not necessary

Certificate of Excellence

from £88 / night

£795 - £978 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £88 / night

(1) Excellent 

30

Colle di Val d'Elsa holiday villa rental

Province of Siena / Colle di Val d'Elsa

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £499 / night

£3,492 - £6,372 / week

Book View

from £499 / night

20

Holiday farmhouse with swimming pool in Guazzino

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £936 / night

£6,547 - £7,769 / week

Enquire View

from £936 / night

(7) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning

from £131 / night

£917 / week

Book View

from £131 / night

21

Isola d'Arbia holiday farmhouse rental

Siena / Isola d'Arbia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £91 / night

£336 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £91 / night

12

B&b rental in Montalcino

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £105 / night

£699 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from £105 / night

19

Holiday villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £160 / night

£1,118 - £2,095 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £160 / night

(1) Very Good 

20

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
  • Pet friendly

from £69 / night

£436 - £680 / week

Book View

Responds fast!
avg. 3 hours 15 minutes

from £69 / night

(7) Excellent 

Certificate of Excellence

72

Radda in Chianti holiday farmhouse rental

Province of Siena / Radda in Chianti

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 120 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £70 / night

£419 / week

Book View

Responds fast!
avg. 3 hours 47 minutes

from £70 / night

10

Apartment rental in Siena

Province of Siena / Siena

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly

from £35 / night

£219 / week

Book View

from £35 / night

(6) Excellent 

22

Apartment rental in Monteriggioni with swimming pool

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £62 / night

£397 - £490 / week

Book View

from £62 / night

(5) Very Good 

20

Holiday farmhouse in Montalcino

Province of Siena / Montalcino

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £110 / night

£764 / week

Book View

from £110 / night

(11) Excellent 

Certificate of Excellence

52

Apartment rental in Montepulciano

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

Certificate of Excellence

from £123 / night

£742 - £926 / week

Book View

Responds fast!
avg. 2 hours 30 minutes

from £123 / night

(3) Excellent 

16

Holiday apartment with swimming pool in Sinalunga

Province of Siena / Sinalunga

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

from £175 / night

£1,171 / week

Book View

from £175 / night

(12) Excellent 

65

Holiday villa in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £464 / night

£3,251 - £4,404 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from £464 / night

(1) Very Good 

10

Siena holiday home rental

Province of Siena / Siena

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden

from £86 / night

£599 / week

Book View

from £86 / night

41

Holiday villa rental

Province of Siena / Montepulciano

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £568 / night

£3,819 - £6,001 / week

Enquire View

from £568 / night

(29) Excellent 

Certificate of Excellence

127

Cottage rental in Pancole

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning
“We want to go back there again!” We stayed there for one week and loved it. Villino del Grillo has a single guest unit and it is separate from the main house. Perfect for a couple. The hosts were very friendly, hospitable and especially helpful. T
…see more

Certificate of Excellence

from £44 / night

£293 - £393 / week

Book View

Responds fast!
avg. 38 minutes

from £44 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

3 6 4 nights min

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

from £86 / night

£602 - £982 / week

Enquire View

from £86 / night

12

Holiday apartment with shared pool in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

2 4 Min stay varies

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

from £79 / night

£550 / week

Book View

from £79 / night

(7) Very Good 

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 £70 / night

£500 - £700 / week

Book View

from £70 / night

(4) Very Good 

14

Poggibonsi holiday apartment rental

Province of Siena / Poggibonsi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £53 / night

£367 - £568 / week

Book View

Responds fast!
avg. 3 hours 21 minutes

from £53 / night

83

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £323 / night

£1,964 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £323 / night

(2) Excellent 

16

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Wonderful peaceful stay in the heart of the Tuscan countryside” The apartment at Radicondoli was wonderful. Just perfect for our requirements. It had everything you could need (except an ironing board). It was exceptionally clean, had an amazing showe
…see more

from £88 / night

£612 - £734 / week

Book View

from £88 / night

50

Holiday apartment in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+

from £284 / night

£1,746 - £2,444 / week

Book View

from £284 / night

(8) Excellent 

17

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

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

from £63 / night

£524 - £830 / week

Book View

Responds fast!
avg. 3 hours 43 minutes

from £63 / night

(1) Very Good 

28

Holiday home in Siena

Province of Siena / Siena

2 4 6 nights min

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

from £53 / night

£350 - £515 / week

Book View

Responds fast!
avg. 2 hours 28 minutes

from £53 / night

(9) Very Good 

6

Valiano holiday home rental

Montepulciano / Valiano

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Pet friendly

from £44 / night

£262 / week

Book View

from £44 / night

(4) Excellent 

36

Holiday apartment in Pienza

Province of Siena / Pienza

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 km
  • Ask owner if suitable for children
  • Pet friendly

from £57 / night

£398 / week

Book View

from £57 / night

(13) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
“Into the bliss!” The moment we arrived at the Autostazione di Montepulciano, Luca greeted us with a big smile and and an open heart that made this trip so particularly memorable. His flat on up on the edge of the hill was as described and better. It c
…see more

from £101 / night

£611 - £758 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £101 / night

9

Holiday home in San Gimignano

Province of Siena / San Gimignano

2 4 2 nights min

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

from £88 / night

£384 / week

Book View

from £88 / night

(1) Excellent 

35

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

2 4 4 nights min

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

from £88 / night

£611 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £88 / night