Search 105,200+ Vacation Rentals

Montalcino Vacation Rentals & Homes with Swimming Pool - 31 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

31 Vacation rentals

Filters applied: Swimming pool

1 / 12

Montalcino Villa

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from $561 / night

1 / 19

Montalcino Apartment

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

from $280 / night

1 / 18

Montalcino Apartment

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

from $312 / night

1 / 50

Montalcino House

  • 8
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $659 / night

(1)

1 / 21

Montalcino Apartment

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

$425

Excellent (1 reviews)

Inquire

from $425 / night

1 / 68

Montalcino Villa

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

from $504 / 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 / 45

Montalcino Villa

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

$320

Book

from $320 / night

(2)

1 / 40

Poggio alle Mura Villa

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1213

Excellent (2 reviews)

Book

from $1213 / night

1 / 20

Montalcino Apartment

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

from $377 / night

1 / 33

Montalcino Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

$1602

Inquire

from $1602 / night

1 / 36

Montalcino Villa

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

$184

Book

from $184 / night

1 / 18

Montalcino Apartment

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

from $296 / 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 / 24

Montalcino House

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $440 / night

1 / 22

Montalcino Villa

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

$292

Book

from $292 / night

1 / 50

Montalcino Villa

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $799 / night

1 / 28

Poggio alle Mura House

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

$729

Book

from $729 / night

1 / 26

Poggio alle Mura Villa

  • 5
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children

$1691

Book

from $1691 / night

1 / 36

Montalcino Villa

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

$264

Book

from $264 / night

1 / 14

Montalcino House

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

from $400 / night

(7)

1 / 60

Montalcino Villa

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

$415

Excellent (7 reviews)

Book

from $415 / night

1 / 30

Montalcino House

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

$3423

Inquire

from $3423 / night

1 / 47

Castelnuovo dell'Abate Villa

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

$1442

Inquire

from $1442 / night

(1)

1 / 39

Montalcino Villa

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

$769

Excellent (1 reviews)

Inquire

from $769 / night

1 / 35

Montalcino Villa

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

$1026

Inquire

from $1026 / night

1 / 25

Montalcino Villa

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

from $505 / night

1 / 17

Montalcino Villa

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Inquire for Rates

Inquire

Pricing unknown

1 / 16

Montalcino Villa

  • 3
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Inquire for Rates

Inquire

Pricing unknown

1 / 43

Poggio alle Mura Villa

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

$1256

Inquire

from $1256 / 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

Your search has been expanded 9.1 miles to include more rentals

1 / 25

San Quirico d'Orcia House - 6.8 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $83 / night

1 / 26

San Quirico d'Orcia House - 6.8 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $83 / night

(1)

1 / 28

San Quirico d'Orcia House - 6.8 miles away

  • 3
  • 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

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $83 / night

1 / 27

San Quirico d'Orcia House - 6.8 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $83 / night

1 / 29

San Quirico d'Orcia House - 6.8 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $136 / night

1 / 20

Buonconvento Villa - 7.5 miles away

  • 22
  • 44
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$14984

Inquire

from $14984 / night

1 / 79

Buonconvento Cottage - 8.9 miles away

  • 22
  • 44
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$19734

Inquire

from $19734 / night

1 / 13

Camigliano Villa - 9.1 miles away

  • 4
  • 8
  • Min stay varies
  • Nearest beach 24 mi
  • Swimming pool

from $320 / night