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Cortona Vacation Rentals & Homes with Swimming Pool - 99 Rentals Available.

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99 Vacation rentals

Filters applied: Swimming pool

1 / 58

Cignano Villa

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

$315.00

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from $315.00 / night

1 / 31

Montalla Villa

  • 4
  • 7
  • 7 nights min
  • Nearest beach 145 mi
  • Swimming pool
  • Child friendly

$152.00

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from $152.00 / night

1 / 22

Montecchio Villa

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

$142.00

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from $142.00 / night

1 / 16

Cortona Villa

  • 10
  • 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,363.00

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from $2,363.00 / night

1 / 27

Cortona Villa

  • 6
  • 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

$510.00

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from $510.00 / night

1 / 43

Cortona Cottage

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

$500.00

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from $500.00 / night

1 / 24

Montecchio Villa

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

$390.00

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from $390.00 / night

1 / 33

Cortona Villa

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$920.00

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from $920.00 / night

(3)

1 / 26

Cortona House

  • 3
  • 6
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 2 hours 6 minutes

$254.00

Excellent (3 reviews)

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from $254.00 / night

1 / 142

Cortona Villa

  • 5
  • 12
  • min stay varies
  • Nearest beach 201 mi
  • Swimming pool
  • Child friendly

$220.00

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from $220.00 / night

1 / 46

Cortona Villa

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

$141.00

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from $141.00 / night

(2)

1 / 26

Mercatale House

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

$287.00

Excellent (2 reviews)

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from $287.00 / night

1 / 56

Cortona Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$356.00

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from $356.00 / night

1 / 17

Cortona House

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

$577.00

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from $577.00 / night

(1)

1 / 38

Cortona Villa

  • 4
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,000.00

Excellent (1 reviews)

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from $1,000.00 / night

(40)

1 / 27

Cortona Villa

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

Responds fast! Avg. 2 hours 6 minutes

$519.00

Excellent (40 reviews)

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from $519.00 / night

1 / 56

Cortona Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$264.00

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from $264.00 / night

Your search has been expanded 19.6 miles to include more rentals

1 / 50

Monterchi Villa - 13.8 miles away

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

$268.00

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from $268.00 / night

1 / 72

Arezzo Villa - 16.4 miles away

  • 5
  • 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

$334.00

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from $334.00 / night

1 / 19

Pozzo di Mulazzo Villa - 9.4 miles away

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

$889.00

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from $889.00 / night

(2)

1 / 41

Lucignano Villa - 12.1 miles away

  • 6
  • 12
  • 7 nights min
  • Nearest beach 217 mi
  • Swimming pool
  • Child friendly

$155.00

Very Good (2 reviews)

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from $155.00 / night

1 / 56

Sinalunga Villa - 13.9 miles away

  • 5
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$359.00

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from $359.00 / night

1 / 50

Monterchi Villa - 13.8 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$491.00

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from $491.00 / night

(3)

1 / 25

Montepulciano Apartment - 13.5 miles away

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

$131.00

Excellent (3 reviews)

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from $131.00 / night

1 / 61

Vaiano Apartment - 14.9 miles away

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

$326.00

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from $326.00 / night

1 / 61

Vaiano Apartment - 14.9 miles away

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

$633.00

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from $633.00 / night

1 / 35

Lucignano Villa - 12.2 miles away

  • 4
  • 8
  • min stay varies
  • Nearest beach 217 mi
  • Swimming pool
  • Child friendly

$167.00

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from $167.00 / night

1 / 35

Castelmuzio Villa - 19.6 miles away

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

$187.00

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from $187.00 / night

1 / 65

Camucia Villa - 2.9 miles away

  • 7
  • 16
  • min stay varies
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly

$326.00

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from $326.00 / night

(1)

1 / 34

Sant'Albino Villa - 16.9 miles away

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

$585.00

Excellent (1 reviews)

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from $585.00 / night

1 / 31

Foiano Della Chiana Villa - 6.1 miles away

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

$311.00

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from $311.00 / night

1 / 79

Lucignano Villa - 10.2 miles away

  • 5
  • 12
  • min stay varies
  • Nearest beach 217 mi
  • Swimming pool
  • Child friendly

$341.00

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from $341.00 / night

1 / 43

Montepulciano Villa - 16.7 miles away

  • 7
  • 16
  • min stay varies
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly

$590.00

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from $590.00 / night

1 / 41

Montepulciano House - 16.6 miles away

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

$572.00

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from $572.00 / night

1 / 52

Lucignano Apartment - 12.3 miles away

  • 6
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$644.00

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from $644.00 / night

1 / 20

Montepulciano House - 14.6 miles away

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

$1,036.00

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from $1,036.00 / night

1 / 49

Monterchi Villa - 13.7 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 1 hour 53 minutes

$505.00

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from $505.00 / night

1 / 56

Brolio House - 6.5 miles away

  • 9
  • 18
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 1 hour 53 minutes

$800.00

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from $800.00 / night

1 / 69

Monterchi Villa - 15.8 miles away

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

Responds fast! Avg. 1 hour 53 minutes

$371.00

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from $371.00 / night

1 / 29

Monte Santa Maria Tiberina Villa - 13.5 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$190.00

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from $190.00 / night