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Province of Siena Vacation Rentals & Homes - 1180 Rentals Available

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1,180 Vacation rentals

1 / 20

Radda in Chianti Apartment

  • 2
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly

$108

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from $108 / night

1 / 19

Montaperti Villa

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

$965

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from $965 / night

(1)

1 / 20

Siena Apartment

  • 3
  • 6
  • 3 nights min
  • Ask about children

$193

Excellent (1 reviews)

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from $193 / night

1 / 41

Siena House

  • 5
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$340

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from $340 / night

1 / 30

Montalcino House

  • 14
  • 30
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$3761

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from $3761 / night

1 / 52

Radda in Chianti House

  • 13
  • 50
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$4255

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from $4255 / night

1 / 13

Monteriggioni Villa

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $258 / night

(2)

1 / 40

Siena Villa

  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$403

Very Good (2 reviews)

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from $403 / night

1 / 28

Volpaia Villa

  • 6
  • 12
  • 7 nights min
  • Child friendly

$372

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from $372 / night

1 / 20

Pianella House

  • 6
  • 10
  • 7 nights min
  • Ask about children

from $296 / night

1 / 54

Monticchiello House

  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $832 / night

1 / 33

Montefollonico House

  • 4
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $828 / night

1 / 20

Casciano House

  • 5
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $513 / night

1 / 20

Chiusdino House

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

from $322 / night

(1)

1 / 23

Bettolle House

  • 10
  • 20
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$828

Excellent (1 reviews)

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from $828 / night

1 / 40

Radicofani Villa

  • 9
  • 17
  • 7 nights min
  • Child friendly

$2177

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from $2177 / night

1 / 20

Isola d'Arbia Apartment

  • 3
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $97 / night

1 / 13

Gaiole in Chianti Villa

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly

from $140 / night

(1)

1 / 29

Poggibonsi Villa

  • 1
  • 4
  • 7 nights min
  • Ask about children

$136

Excellent (1 reviews)

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from $136 / night

1 / 25

Siena House

  • 6
  • 11
  • 7 nights min
  • Swimming pool

from $532 / night

1 / 24

Campiglia d'Orcia Apartment

  • 1
  • 5
  • 1 night min
  • Ask about children
  • Ask about pets

$130

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from $130 / night

1 / 45

Siena Villa

  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$230

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from $230 / night

(7)

1 / 49

Castellina In Chianti Farmhouse

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

$460

Very Good (7 reviews)

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from $460 / night

(3)

1 / 24

Volpaia Villa

  • 6
  • 11
  • 7 nights min
  • Swimming pool
  • Ask about children

$505

Very Good (3 reviews)

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from $505 / night

1 / 20

Volpaia House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children

$426

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from $426 / night

1 / 32

Radda in Chianti Farmhouse

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

from $653 / night

1 / 45

Montalcino Villa

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

$355

Book

from $355 / night

(1)

1 / 28

Radda in Chianti House

  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1127

Very Good (1 reviews)

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from $1127 / night

(1)

1 / 33

Lucarelli Villa

  • 6
  • 10
  • 7 nights min
  • Child friendly
  • Pet friendly

$466

Excellent (1 reviews)

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from $466 / night

1 / 14

Siena Apartment

  • 1
  • 2
  • 7 nights min
  • Ask about children

from $134 / night

1 / 21

San Quirico d'Orcia Villa

  • 6
  • 12
  • 7 nights min
  • Ask about children
  • Ask about pets

$1447

Book

from $1447 / night

1 / 20

Asciano Apartment

  • 3
  • 6
  • 3 nights min
  • Ask about children

from $198 / night

1 / 21

Montecchio Villa

  • 4
  • 8
  • 7 nights min
  • Child friendly

$402

Book

from $402 / night

1 / 30

Castel San Gimignano House

  • 1
  • 3
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

from $65 / night

1 / 16

Colle di Val d'Elsa House

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $152 / night

1 / 26

Cetona Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $608 / night

1 / 10

Poggibonsi House

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

from $136 / night

1 / 28

Monteriggioni House

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

$230

Book

from $230 / night

1 / 0

Poggibonsi Villa

  • 1
  • 2
  • 7 nights min
  • Ask about children

from $109 / night

1 / 35

Montepulciano House

  • 7
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $542 / night