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5 Best Vacation Rentals in Portland - Holiday Lettings - Cabins

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102 Vacation rentals

Vacation home in Portland

Portland house

4 bedrooms • 2 bathrooms • sleeps 9

from $659 / night

$7,414 / week

1 / 71

Portland Vacation condo rental

Portland condo

1 bedroom • 1 bathroom • sleeps 3

from $327 / night

$2,285 / week

1 / 45

Portland Vacation apartment rental

Portland apartment

3 bedrooms • 2 bathrooms • sleeps 8

from $527 / night

$3,126 / week

1 / 32

Portland Vacation apartment rental

Portland apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $498 / night

$2,964 / week

1 / 33

Apartment rental in Portland

Portland apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $235 / night

$1,643 / week

1 / 28

Apartment rental in Portland

Portland apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $235 / night

$1,643 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation home in Old Orchard Beach

Old Orchard Beach house

2 bedrooms • 1 bathroom • sleeps 6

from $172 / night

$1,145 / week

1 / 12

Vacation cottage in Biddeford Pool

Biddeford Pool cottage

2 bedrooms • 1 bathroom • sleeps 6

from $344 / night

$2,405 / week

1 / 15

Falmouth Vacation home rental

Falmouth house

3 bedrooms • 1 bathroom • sleeps 6

from $796 / night

$4,552 / week

1 / 42

Vacation home in Scarborough

Scarborough house

4 bedrooms • 6 bathrooms • sleeps 10

from $1,145 / night

$8,015 / week

1 / 15

Vacation home rental

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 8

from $304 / night

$2,119 / week

1 / 8

Vacation cottage in Old Orchard Beach

Old Orchard Beach cottage

3 bedrooms • 1 bathroom • sleeps 8

from $262 / night

$1,832 / week

1 / 14

Vacation apartment in Old Orchard Beach

Old Orchard Beach apartment

3 bedrooms • 1 bathroom • sleeps 10

from $409 / night

$2,863 / week

1 / 21

Vacation condo in Scarborough

Scarborough condo

1 bedroom • 1 bathroom • sleeps 2

from $126 / night

$1,031 / week

1 / 27

Home rental in South Portland

South Portland house

3 bedrooms • 2 bathrooms • sleeps 9

from $796 / night

$3,979 / week

1 / 89

Vacation condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $262 / night

$1,832 / week

1 / 11

Vacation guest house in Biddeford

Biddeford guest house

1 bedroom • 1 bathroom • sleeps 4

from $745 / night

$5,210 / week

1 / 16

Old Orchard Beach Vacation cottage rental

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from $310 / night

$2,164 / week

1 / 29

Old Orchard Beach Vacation cottage rental

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from $308 / night

$2,156 / week

1 / 27

Vacation home in Old Orchard Beach

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 6

from $295 / night

$2,061 / week

1 / 12

Vacation home in Ocean Park

Ocean Park house

3 bedrooms • 1 bathroom • sleeps 8

from $281 / night

$1,964 / week

1 / 10

Vacation home with golf nearby in South Portland

South Portland house

4 bedrooms • 3 bathrooms • sleeps 10

from $1,254 / night

$5,697 / week

1 / 78

West Scarborough Vacation home rental

West Scarborough house

2 bedrooms • 1 bathroom • sleeps 8

from $315 / night

$2,205 / week

1 / 17

Vacation home rental

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 7

from $338 / night

$2,365 / week

1 / 13

Vacation apartment in Old Orchard Beach

Old Orchard Beach apartment

3 bedrooms • 1 bathroom • sleeps 10

from $409 / night

$2,863 / week

1 / 11

Scarborough Vacation home rental

Scarborough house

6 bedrooms • 3 bathrooms • sleeps 19

from $2,127 / night

$14,885 / week

1 / 34

Vacation cottage in Old Orchard Beach

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from $238 / night

$1,661 / week

1 / 10

Vacation apartment in Old Orchard Beach

Old Orchard Beach apartment

2 bedrooms • 1 bathroom • sleeps 5

from $491 / night

$3,435 / week

1 / 28

Cape Elizabeth Vacation home rental

Cape Elizabeth house

5 bedrooms • 4 bathrooms • sleeps 10

from $1,117 / night

$6,842 / week

1 / 77

Vacation condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $469 / night

$3,279 / week

1 / 12

Vacation condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $480 / night

$3,359 / week

1 / 12

Vacation condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $457 / night

$3,198 / week

1 / 12

Vacation condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from $446 / night

$3,118 / week

1 / 20

Vacation condo rental

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from $457 / night

$3,198 / week

1 / 20

Vacation condo in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from $457 / night

$3,198 / week

1 / 10

Vacation condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $492 / night

$3,439 / week

1 / 13

Vacation condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $464 / night

$3,246 / week

1 / 12

Vacation condo in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from $446 / night

$3,118 / week

1 / 16

Old Orchard Beach Vacation condo rental

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $446 / night

$3,118 / week

1 / 12

Vacation condo accommodation

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $446 / night

$3,118 / week

1 / 13