Search 105,200+ Vacation Rentals

Montalcino Vacation Rentals & Homes with Swimming Pool - 40 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

33 Vacation rentals

Filters applied: Swimming pool

1 / 22

Montalcino Villa

  • 4
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$293

Book

from $293 / night

1 / 36

Montalcino Villa

  • -1
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$267

Book

from $267 / night

1 / 36

Montalcino Villa

  • -1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$184

Book

from $184 / night

1 / 39

Montalcino House

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$582

Book

from $582 / night

1 / 50

Montalcino House

  • -1
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $660 / night

1 / 20

Montalcino Apartment

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

from $378 / night

1 / 30

Montalcino House

  • -1
  • 30
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$3430

Inquire

from $3430 / night

(1)

1 / 39

Montalcino Villa

  • -1
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children

$770

Excellent (1 reviews)

Inquire

from $770 / night

(2)

1 / 40

Poggio alle Mura Villa

  • -1
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1215

Excellent (2 reviews)

Book

from $1215 / night

1 / 19

Montalcino Apartment

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

from $281 / night

1 / 18

Montalcino Apartment

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

from $313 / night

1 / 67

Montalcino Farmhouse

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $494 / night

1 / 50

Montalcino Villa

  • -1
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $800 / night

1 / 45

Montalcino Villa

  • -1
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$324

Book

from $324 / night

1 / 14

Montalcino House

  • -1
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children

from $401 / night

(34)

1 / 52

Montalcino Farmhouse

  • -1
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$326

Very Good (34 reviews)

Inquire

from $326 / night

(1)

1 / 21

Montalcino Apartment

  • 3
  • 6
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Pet friendly

$426

Excellent (1 reviews)

Inquire

from $426 / night

1 / 60

Montalcino Villa

  • -1
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$416

Book

from $416 / night

1 / 18

Montalcino Apartment

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

from $297 / night

1 / 68

Montalcino Villa

  • -1
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $504 / night

1 / 28

Poggio alle Mura House

  • -1
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children

$730

Book

from $730 / night

1 / 35

Montalcino Villa

  • -1
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1026

Inquire

from $1026 / night

1 / 24

Montalcino House

  • -1
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $440 / night

1 / 23

Montalcino House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$1154

Inquire

from $1154 / night

1 / 26

Poggio alle Mura Villa

  • -1
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children

$1694

Book

from $1694 / night

1 / 47

Castelnuovo dell'Abate Villa

  • 5
  • 8
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$1444

Inquire

from $1444 / night

1 / 25

Montalcino Villa

  • -1
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $505 / night

1 / 43

Poggio alle Mura Villa

  • -1
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1256

Inquire

from $1256 / night

(2)

1 / 14

Montalcino House

  • -1
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1143

Very Good (2 reviews)

Inquire

from $1143 / night

1 / 50

Poggio alle Mura Villa

  • -1
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1783

Inquire

from $1783 / night

1 / 18

Montalcino House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $724 / night

1 / 16

Montalcino Villa

  • -1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$3310

Inquire

from $3310 / night

1 / 17

Montalcino Villa

  • -1
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$3557

Inquire

from $3557 / night

Your search has been expanded 7.5 miles to include more rentals

1 / 25

San Quirico d'Orcia House - 6.8 miles away

  • -1
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $84 / night

1 / 26

San Quirico d'Orcia House - 6.8 miles away

  • -1
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $84 / night

(1)

1 / 28

San Quirico d'Orcia House - 6.8 miles away

  • -1
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$108

Excellent (1 reviews)

Inquire

from $108 / night

1 / 24

San Quirico d'Orcia House - 6.8 miles away

  • -1
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $84 / night

1 / 27

San Quirico d'Orcia House - 6.8 miles away

  • -1
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $84 / night

1 / 29

San Quirico d'Orcia House - 6.8 miles away

  • -1
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $136 / night

1 / 20

Buonconvento Villa - 7.5 miles away

  • -1
  • 44
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$15011

Inquire

from $15011 / night