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Search 105,200+ Vacation Rentals

Isle of Portland Vacation Rentals & Homes - 507 Rentals Available

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507 Vacation rentals

1 / 25

Easton House

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Private garden

$143.00

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from $143.00 / night

(3)

1 / 26

Weston House

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

$201.00

Very Good (3 reviews)

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from $201.00 / night

(10)

1 / 17

Weston House

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

$201.00

Very Good (10 reviews)

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from $201.00 / night

1 / 14

Easton Cottage

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly

$215.00

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from $215.00 / night

(7)

1 / 12

Fortuneswell Apartment

  • 1
  • 2
  • 3 nights min
  • Child friendly
  • Pet friendly

$153.00

Excellent (7 reviews)

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from $153.00 / night

(1)

1 / 32

Fortuneswell Cottage

  • 2
  • 4
  • 3 nights min
  • Child friendly

$188.00

Excellent (1 reviews)

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from $188.00 / night

1 / 25

Easton Cottage

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly

$210.00

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from $210.00 / night

1 / 27

Fortuneswell Cottage

  • 3
  • 6
  • 3 nights min
  • Child friendly

$230.00

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from $230.00 / night

(1)

1 / 29

Castletown Cottage

  • 4
  • 8
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$343.00

Excellent (1 reviews)

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from $343.00 / night

1 / 20

Weston Bungalow

  • 1
  • 2
  • 3 nights min
  • Child friendly
  • Private garden

$209.00

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from $209.00 / night

1 / 33

Castletown Cottage

  • 4
  • 8
  • 3 nights min
  • Private garden

$427.00

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from $427.00 / night

(1)

1 / 30

Fortuneswell Cottage

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$195.00

Excellent (1 reviews)

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from $195.00 / night

1 / 27

Castletown Cottage

  • 4
  • 8
  • 3 nights min
  • Child friendly

$260.00

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from $260.00 / night

1 / 22

Castletown Apartment

  • 2
  • 4
  • 3 nights min

$195.00

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from $195.00 / night

(1)

1 / 20

Castletown Cottage

  • 3
  • 5
  • 3 nights min
  • Pet friendly
  • Private garden

$202.00

Excellent (1 reviews)

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from $202.00 / night

1 / 19

Fortuneswell Cottage

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Private garden

$204.00

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from $204.00 / night

1 / 19

Easton Cottage

  • 2
  • 4
  • 3 nights min
  • Private garden

$182.00

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from $182.00 / night

1 / 32

Fortuneswell Cottage

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly

$188.00

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from $188.00 / night

1 / 20

Fortuneswell Cottage

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly

$202.00

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from $202.00 / night

1 / 28

Weston Cottage

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Private garden

$229.00

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from $229.00 / night

(1)

1 / 22

Fortuneswell Cottage

  • 3
  • 6
  • 3 nights min

$276.00

Very Good (1 reviews)

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from $276.00 / night

1 / 70

Weston Cottage

  • 9
  • 20
  • 3 nights min
  • Swimming pool
  • Child friendly

$2,602.00

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from $2,602.00 / night

1 / 21

Castletown Cottage

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$215.00

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from $215.00 / night

(1)

1 / 30

Castletown Cottage

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly

$234.00

Very Good (1 reviews)

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from $234.00 / night

1 / 43

Castletown House

  • 4
  • 7
  • 3 nights min
  • Child friendly
  • Private garden

$343.00

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from $343.00 / night

1 / 54

Easton House

  • 3
  • 6
  • 3 nights min
  • Private garden

$276.00

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from $276.00 / night

1 / 28

Castletown House

  • 2
  • 4
  • 3 nights min
  • Private garden

$212.00

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from $212.00 / night

1 / 30

Castletown House

  • 2
  • 4
  • 3 nights min
  • Private garden

$212.00

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from $212.00 / night

1 / 41

Weston House

  • 2
  • 4
  • 3 nights min
  • Private garden

$216.00

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from $216.00 / night

1 / 42

Castletown House

  • 3
  • 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$210.00

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from $210.00 / night

1 / 33

Fortuneswell House

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Private garden

$190.00

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from $190.00 / night

1 / 52

Fortuneswell Cottage

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Private garden

$236.00

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from $236.00 / night

1 / 18

Fortuneswell Cottage

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly

$217.00

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from $217.00 / night

(1)

1 / 34

Weston Cottage

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$168.00

Average (1 reviews)

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from $168.00 / night

1 / 41

Fortuneswell House

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Private garden

$416.00

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from $416.00 / night

1 / 22

Castletown Apartment

  • 1
  • 2
  • 3 nights min

$149.00

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from $149.00 / night

1 / 21

Weston Apartment

  • 2
  • 4
  • 3 nights min
  • Child friendly

$215.00

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from $215.00 / night

1 / 23

Castletown Cottage

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$198.00

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from $198.00 / night

1 / 23

Fortuneswell Cottage

  • 1
  • 2
  • 3 nights min

$198.00

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from $198.00 / night

1 / 21

Fortuneswell House

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly

$217.00

Inquire

from $217.00 / night