Search 105,200+ Vacation Rentals

Cortona Vacation Rentals & Homes with Swimming Pool - 637 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

637 Vacation rentals

Filters applied: Swimming pool

1 / 23

Montalla House

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

$256.00

Book

from $256.00 / night

(2)

1 / 44

Montalla Villa

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

$278.00

Excellent (2 reviews)

Book

from $278.00 / night

1 / 19

Cortona Apartment

  • 2
  • 4
  • 4 nights min
  • Swimming pool
  • Child friendly

$99.00

Book

from $99.00 / night

1 / 32

Cortona Villa

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$151.00

Book

from $151.00 / night

1 / 36

Cortona Villa

  • 3
  • 6
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Ask about children

$247.00

Book

from $247.00 / night

1 / 48

Montalla Villa

  • 3
  • 8
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Ask about children

$226.00

Book

from $226.00 / night

1 / 26

Mercatale Villa

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

$298.00

Inquire

from $298.00 / night

1 / 20

Cortona Apartment

  • 2
  • 4
  • 4 nights min
  • Swimming pool
  • Child friendly

$99.00

Book

from $99.00 / night

(3)

1 / 36

Cortona Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$203.00

Excellent (3 reviews)

Book

from $203.00 / night

(1)

1 / 24

Cortona Villa

  • 9
  • 22
  • 7 nights min
  • Nearest beach 152 mi
  • Swimming pool
  • Ask about children

$533.00

Excellent (1 reviews)

Book

from $533.00 / night

1 / 46

Cortona Villa

  • 3
  • 5
  • 7 nights min
  • Nearest beach 145 mi
  • Swimming pool
  • Child friendly

$135.00

Inquire

from $135.00 / night

1 / 19

Cortona House

  • 3
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly

$191.00

Book

from $191.00 / night

(1)

1 / 27

Cortona House

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Child friendly

$205.00

Excellent (1 reviews)

Book

from $205.00 / night

1 / 52

Cortona Villa

  • 5
  • 12
  • 7 nights min
  • Nearest beach 135 mi
  • Swimming pool
  • Ask about children

$311.00

Book

from $311.00 / night

1 / 22

Montecchio Villa

  • 2
  • 4
  • min stay varies
  • Nearest beach 249 mi
  • Swimming pool
  • Child friendly

$149.00

Inquire

from $149.00 / night

(4)

1 / 40

Cortona Villa

  • 4
  • 8
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Ask about children

$276.00

Excellent (4 reviews)

Book

from $276.00 / night

1 / 19

Cortona Apartment

  • 2
  • 4
  • 4 nights min
  • Swimming pool
  • Child friendly

$82.00

Book

from $82.00 / night

(4)

1 / 48

Cortona Villa

  • 1
  • 4
  • 7 nights min
  • Nearest beach 158 mi
  • Swimming pool
  • Ask about children

$186.00

Excellent (4 reviews)

Book

from $186.00 / night

1 / 33

Cortona Apartment

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

$248.00

Inquire

from $248.00 / night

1 / 18

Cortona Apartment

  • 1
  • 4
  • 4 nights min
  • Swimming pool
  • Child friendly

$74.00

Book

from $74.00 / night

(1)

1 / 18

Cortona Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$167.00

Very Good (1 reviews)

Book

from $167.00 / night

1 / 32

Cortona Villa

  • 5
  • 9
  • 7 nights min
  • Nearest beach 152 mi
  • Swimming pool
  • Ask about children

$324.00

Book

from $324.00 / night

1 / 49

Cortona House

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

$354.00

Inquire

from $354.00 / night

1 / 72

Cortona Villa

  • 8
  • 20
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$537.00

Book

from $537.00 / night

(3)

1 / 54

Cortona Villa

  • 3
  • 6
  • 7 nights min
  • Nearest beach 160 mi
  • Swimming pool
  • Ask about children

$297.00

Excellent (3 reviews)

Book

from $297.00 / night

1 / 44

Cortona Villa

  • 4
  • 8
  • 7 nights min
  • Nearest beach 135 mi
  • Swimming pool
  • Ask about children

$243.00

Book

from $243.00 / night

1 / 24

Montecchio Villa

  • 3
  • 7
  • min stay varies
  • Nearest beach 155 mi
  • Swimming pool
  • Child friendly

$189.00

Inquire

from $189.00 / night

1 / 30

Cortona Farmhouse

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

$468.00

Inquire

from $468.00 / night

1 / 69

Creti Villa

  • 6
  • 14
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Ask about children

$556.00

Book

from $556.00 / night

1 / 24

Cortona Villa

  • 2
  • 4
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Ask about children

$167.00

Book

from $167.00 / night

(2)

1 / 24

Cortona Villa

  • 7
  • 14
  • 7 nights min
  • Nearest beach 152 mi
  • Swimming pool
  • Ask about children

$427.00

Very Good (2 reviews)

Book

from $427.00 / night

(1)

1 / 78

Montalla Villa

  • 9
  • 18
  • 7 nights min
  • Nearest beach 180 mi
  • Swimming pool
  • Ask about children

$1,016.00

Excellent (1 reviews)

Book

from $1,016.00 / night

1 / 13

Cortona House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$224.00

Inquire

from $224.00 / night

1 / 64

Cortona Villa

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$389.00

Book

from $389.00 / night

1 / 32

Cignano Villa

  • 7
  • 17
  • min stay varies
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly

$315.00

Inquire

from $315.00 / night

1 / 35

Cortona Villa

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$356.00

Book

from $356.00 / night

(2)

1 / 19

Mercatale House

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

$270.00

Excellent (2 reviews)

Inquire

from $270.00 / night

1 / 18

Cortona Villa

  • 4
  • 7
  • 7 nights min
  • Nearest beach 225 mi
  • Swimming pool
  • Child friendly

$203.00

Inquire

from $203.00 / night

1 / 27

Cortona Villa

  • 5
  • 12
  • 7 nights min
  • Nearest beach 201 mi
  • Swimming pool
  • Child friendly

$188.00

Inquire

from $188.00 / night

1 / 28

Cortona Villa

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

$240.00

Inquire

from $240.00 / night