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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 - $9,132 / 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 apartment in Old Orchard Beach

Old Orchard Beach apartment

2 bedrooms • 1 bathroom • sleeps 5

from $491 / night

$3,435 / week

1 / 28

Old Orchard Beach Vacation cottage rental

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

1 review

from $310 / night

$2,164 / week

1 / 29

Windham Vacation condo rental

Windham condo

1 bedroom • 1 bathroom • sleeps 2

from $279 / night

$1,948 / week

1 / 5

Vacation home in Scarborough

Scarborough house

4 bedrooms • 6 bathrooms • sleeps 10

from $1,145 / night

$8,015 / week

1 / 15

Old Orchard Beach Vacation cottage rental

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

1 review

from $308 / night

$2,156 / week

1 / 27

Vacation private room in Old Orchard Beach

Old Orchard Beach private room

1 bedroom • 1 bathroom • sleeps 2

from $81 / night

$561 / week

1 / 12

Vacation cottage in Old Orchard Beach

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from $238 / night

$1,661 / week

1 / 10

Cottage rental in Harpswell

Harpswell cottage

3 bedrooms • 1 bathroom • sleeps 6

5 reviews

from $254 / night

$1,775 - $4,180 / week

1 / 20

Windham Vacation condo rental

Windham condo

3 bedrooms • 2 bathrooms • sleeps 8

from $492 / night

$3,439 / week

1 / 8

Home rental in Scarborough

Scarborough house

7 bedrooms • 5 bathrooms • sleeps 28

from $2,262 / night

$13,168 - $19,231 / week

1 / 63

Vacation cottage in Biddeford Pool

Biddeford Pool cottage

2 bedrooms • 1 bathroom • sleeps 6

5 reviews

from $344 / night

$2,405 / week

1 / 15

Cape Elizabeth Vacation castle rental

Cape Elizabeth castle

6 bedrooms • 7 bathrooms • sleeps 12

from $3,435 / night

$24,045 / week

1 / 47

Vacation condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

10 reviews

from $262 / night

$1,832 / week

1 / 11

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

Vacation home rental

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 7

1 review

from $338 / night

$2,365 / week

1 / 13

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 rental

Old Orchard Beach condo

2 bedrooms • 2 bathrooms • sleeps 4

from $92 / night

$642 / week

1 / 50

Vacation guest house in Biddeford

Biddeford guest house

1 bedroom • 1 bathroom • sleeps 4

from $745 / night

$5,210 / week

1 / 16

Vacation home in Old Orchard Beach

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from $295 / night

$2,061 / week

1 / 12

Vacation apartment in Old Orchard Beach

Old Orchard Beach apartment

3 bedrooms • 1 bathroom • sleeps 10

from $409 / night

$2,863 / week

1 / 11

Vacation home in Ocean Park

Ocean Park house

3 bedrooms • 1 bathroom • sleeps 8

from $281 / night

$1,964 / week

1 / 10

Cottage rental in Biddeford Pool

Biddeford Pool cottage

3 bedrooms • 2 bathrooms • sleeps 6

from $409 / night

$2,863 / week

1 / 5

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

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

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 $480 / night

$3,359 / week

1 / 13

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

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 in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $457 / night

$3,198 / 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 accommodation

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from $446 / night

$3,118 / week

1 / 13

West Scarborough Vacation home rental

West Scarborough house

2 bedrooms • 1 bathroom • sleeps 8

from $315 / night

$2,205 / week

1 / 17