Search 105,200+ Vacation Rentals

Province of Siena Vacation Rentals & Homes - 277 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

277 Vacation rentals

1 / 41

Buonconvento Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$1,856.00

Inquire

from $1,856.00 / night

1 / 35

Ville di Corsano Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$2,421.00

Inquire

from $2,421.00 / night

(17)

1 / 38

Montepulciano Apartment

  • 2
  • 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$132.00

Excellent (17 reviews)

Inquire

from $132.00 / night

1 / 42

Poggio alle Mura Villa

  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,205.00

Inquire

from $1,205.00 / night

1 / 18

Montalcino Apartment

  • 2
  • 4
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Child friendly

$346.00

Inquire

from $346.00 / night

(2)

1 / 39

Montepulciano Apartment

  • 1
  • 2
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$93.00

Very Good (2 reviews)

Inquire

from $93.00 / night

1 / 12

Pievescola Villa

  • 2
  • 4
  • min stay varies
  • Child friendly

$1,412.00

Inquire

from $1,412.00 / night

(1)

1 / 29

Castelnuovo dell'Abate Villa

  • 5
  • 8
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$1,494.00

Excellent (1 reviews)

Inquire

from $1,494.00 / night

(11)

1 / 33

Montepulciano Apartment

  • 2
  • 5
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$115.00

Excellent (11 reviews)

Inquire

from $115.00 / night

1 / 37

San Casciano dei Bagni Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$3,229.00

Inquire

from $3,229.00 / night

(9)

1 / 34

Montepulciano Apartment

  • 3
  • 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$132.00

Very Good (9 reviews)

Inquire

from $132.00 / night

1 / 22

San Casciano dei Bagni Villa

  • 7
  • 14
  • 7 nights min
  • Child friendly

$1,453.00

Inquire

from $1,453.00 / night

(34)

1 / 46

Montalcino Farmhouse

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$343.00

Very Good (34 reviews)

Inquire

from $343.00 / night

1 / 19

San Casciano dei Bagni Villa

  • 7
  • 14
  • 7 nights min
  • Child friendly
  • Ask about pets

$2,768.00

Inquire

from $2,768.00 / night

1 / 31

San Casciano dei Bagni Farmhouse

  • 13
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,944.00

Inquire

from $1,944.00 / night

(2)

1 / 39

Montepulciano Apartment

  • 2
  • 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$132.00

Excellent (2 reviews)

Inquire

from $132.00 / night

1 / 37

San Gimignano Villa

  • 8
  • 16
  • min stay varies
  • Child friendly
  • Ask about pets

$1,776.00

Inquire

from $1,776.00 / night

1 / 11

Pievescola Villa

  • 3
  • 6
  • min stay varies
  • Child friendly

$1,412.00

Inquire

from $1,412.00 / night

1 / 18

Montalcino Apartment

  • 2
  • 4
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Child friendly

$335.00

Inquire

from $335.00 / night

1 / 21

Castelnuovo Berardenga Villa

  • 9
  • 16
  • 7 nights min
  • Child friendly

$1,268.00

Inquire

from $1,268.00 / night

(3)

1 / 25

Montepulciano Apartment

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Pet friendly

$134.00

Excellent (3 reviews)

Inquire

from $134.00 / night

1 / 27

Pienza Villa

  • 6
  • 12
  • min stay varies
  • Child friendly

$972.00

Inquire

from $972.00 / night

1 / 20

Montalcino Apartment

  • 2
  • 6
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Child friendly

$424.00

Inquire

from $424.00 / night

1 / 32

Radda in Chianti Farmhouse

  • 11
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$618.00

Inquire

from $618.00 / night

(1)

1 / 148

Pienza Villa

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 15 minutes

$622.00

Excellent (1 reviews)

Book

from $622.00 / night

1 / 35

Castelmuzio Villa

  • 2
  • 6
  • min stay varies
  • Nearest beach 161 mi
  • Swimming pool
  • Child friendly

$168.00

Inquire

from $168.00 / night

1 / 21

Siena Apartment

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 10 minutes

$246.00

Book

from $246.00 / night

(1)

1 / 22

San Gusme Villa

  • 2
  • 6
  • 7 nights min
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$210.00

Excellent (1 reviews)

Inquire

from $210.00 / night

1 / 33

Ponte a Bozzone Villa

  • 5
  • 10
  • 7 nights min
  • Child friendly

$2,249.00

Inquire

from $2,249.00 / night

1 / 32

Radda in Chianti Farmhouse

  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$618.00

Inquire

from $618.00 / night

(1)

1 / 47

Pienza House

  • 7
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$1,200.00

Very Good (1 reviews)

Inquire

from $1,200.00 / night

(5)

1 / 70

Monteriggioni House

  • 17
  • 34
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$4,017.00

Excellent (5 reviews)

Inquire

from $4,017.00 / night

1 / 29

Pienza Villa

  • 8
  • 14
  • min stay varies
  • Child friendly
  • Ask about pets

$972.00

Inquire

from $972.00 / night

(7)

1 / 46

Castellina In Chianti Farmhouse

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$469.00

Very Good (7 reviews)

Inquire

from $469.00 / night

1 / 20

San Giovanni d'Asso Villa

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 15 minutes

$788.00

Book

from $788.00 / night

(3)

1 / 33

Castellina In Chianti Farmhouse

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$201.00

Very Good (3 reviews)

Inquire

from $201.00 / night

(1)

1 / 34

Sant'Albino Villa

  • 7
  • 21
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly

$574.00

Excellent (1 reviews)

Inquire

from $574.00 / night

(5)

1 / 36

Castellina In Chianti Farmhouse

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$175.00

Very Good (5 reviews)

Inquire

from $175.00 / night

1 / 40

Poggio alle Mura Villa

  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,738.00

Inquire

from $1,738.00 / night

1 / 33

Montefollonico Villa

  • 5
  • 10
  • 7 nights min
  • Ask about children
  • Ask about pets

$1,036.00

Inquire

from $1,036.00 / night