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Best Vacation Rentals in Happy Bay - Holiday Lettings - Cabins

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825 Vacation rentals

Great rentals within 20 miles that match your search

Vacation villa rental

Cole Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $630 / night

$4,180 - $4,924 / week

1 / 28

Great rentals within 20 miles that match your search

Apartment rental in The Valley with shared pool

The Valley apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $126 / night

$882 / week

1 / 6

Great rentals within 20 miles that match your search

Vacation studio with shared pool in Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 3

from $161 / night

$1,123 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Orient Bay

Orient Bay villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 16

from $619 / night

$3,649 - $5,133 / week

1 / 33

Great rentals within 20 miles that match your search

Philipsburg Vacation condo rental

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $401 / night

$2,806 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $573 / night

$4,008 / week

1 / 42

Great rentals within 20 miles that match your search

Vacation private room in Cupecoy Bay

Cupecoy Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $172 / night

$1,231 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation apartment in Oyster Pond

Oyster Pond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $353 / night

$2,474 / week

1 / 5

Great rentals within 20 miles that match your search

Vacation villa rental

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $745 / night

$5,210 / week

1 / 36

Great rentals within 20 miles that match your search

Orient Bay Vacation apartment rental

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $307 / night

$2,143 / week

1 / 58

Great rentals within 20 miles that match your search

Terres Basses Vacation villa rental

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $900 / night

$6,300 - $18,200 / week

1 / 28

Great rentals within 20 miles that match your search

Hotel apartment rental in Marigot, Saint Martin with shared pool

Marigot, Saint Martin hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $458 / night

$3,206 / week

1 / 4

Great rentals within 20 miles that match your search

Villa rental in Little Harbour

Little Harbour villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 22

from $10,534 / night

$73,738 / week

1 / 4

Great rentals within 20 miles that match your search

Little Harbour Vacation villa rental

Little Harbour villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 22

from $9,389 / night

$65,723 / week

1 / 6

Great rentals within 20 miles that match your search

Vacation home in Terres Basses

Terres Basses house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 24

from $2,786 / night

$19,500 - $50,000 / week

1 / 68

Great rentals within 20 miles that match your search

Home rental in Oyster Pond

Oyster Pond house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $344 / night

$2,405 / week

1 / 93

Great rentals within 20 miles that match your search

Penthouse rental in Oyster Pond with shared pool

Oyster Pond penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $490 / night

$3,430 / week

1 / 15

Great rentals within 20 miles that match your search

Apartment rental in Orient Bay with shared pool

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $161 / night

$1,126 - $1,559 / week

1 / 22

Great rentals within 20 miles that match your search

Terres Basses Vacation villa rental

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $2,143 / night

$15,000 - $40,000 / week

1 / 76

Great rentals within 20 miles that match your search

Terres Basses Vacation villa rental

Terres Basses villa

  • 14 bedrooms
  • 13 bathrooms
  • sleeps 26

from $5,000 / night

$35,000 - $110,000 / week

1 / 97

Great rentals within 20 miles that match your search

Vacation villa in Marigot, Saint Martin

Marigot, Saint Martin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $378 / night

$1,720 - $6,914 / week

1 / 24

Great rentals within 20 miles that match your search

Villa rental in Terres Basses

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,039 / night

$7,275 - $20,995 / week

1 / 32

Great rentals within 20 miles that match your search

Terres Basses Vacation villa rental

Terres Basses villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

from $4,518 / night

$31,626 - $79,200 / week

1 / 49

Great rentals within 20 miles that match your search

Vacation villa with swimming pool, golf nearby in Maho

Maho villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $858 / night

$6,006 - $12,005 / week

1 / 76

Great rentals within 20 miles that match your search

Vacation villa in Terres Basses

Terres Basses villa

  • 14 bedrooms
  • 15 bathrooms
  • sleeps 28

from $5,000 / night

$35,000 - $110,000 / week

1 / 95

Great rentals within 20 miles that match your search

Vacation hotel apartment in Oyster Pond

Oyster Pond hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $884 / night

$6,184 / week

1 / 11

Great rentals within 20 miles that match your search

Home rental in Terres Basses with swimming pool

Terres Basses house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from $1,143 / night

$8,000 - $23,000 / week

1 / 54

Great rentals within 20 miles that match your search

Home rental in Terres Basses

Terres Basses house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

from $1,910 / night

$13,369 / week

1 / 38

Great rentals within 20 miles that match your search

Terres Basses Vacation villa rental

Terres Basses villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

from $5,214 / night

$36,500 - $136,500 / week

1 / 44

Great rentals within 20 miles that match your search

Villa rental in Long Bay Village

Long Bay Village villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 21

from $6,641 / night

$46,487 / week

1 / 74

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Orient Bay

Orient Bay villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $435 / night

$3,042 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation villa in West End Village

West End Village villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 18

from $13,168 / night

$92,173 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation condo with shared pool in Oyster Pond

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $434 / night

$3,035 / week

1 / 5

Great rentals within 20 miles that match your search

Cupecoy Bay Vacation apartment rental

Cupecoy Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $400 / night

$2,800 - $7,000 / week

1 / 40

Great rentals within 20 miles that match your search

Vacation home in Terres Basses

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,300 / night

$9,100 - $20,895 / week

1 / 44

Great rentals within 20 miles that match your search

Vacation villa in Cupecoy Bay

Cupecoy Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $277 / night

$1,939 / week

1 / 37

Great rentals within 20 miles that match your search

Apartment rental in Simpson Bay with shared pool

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $571 / night

$3,973 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation condo with shared pool in Oyster Pond

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $295 / night

$2,061 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Oyster Pond

Oyster Pond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $155 / night

$990 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,143 / night

$8,000 - $23,000 / week

1 / 24