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Best Caribbean Villas on Holiday Lettings - Vacation rentals

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55,616 Vacation rentals

Vacation villa in Martinique

Le Diamant villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $314 / night

$2,198 / week

1 / 30

U.S. Virgin Islands Vacation condo rental

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from $438 / night

$3,066 / week

1 / 30

Aruba ski condo to rent.

Oranjestad condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $489 / night

$3,423 / week

1 / 30

Vacation condo rental

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from $403 / night

$2,821 / week

1 / 30

Condo rental in Caribbean

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $475 / night

$3,325 / week

1 / 30

Vacation home rental

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from $794 / night

$5,558 / week

1 / 18

Caribbean Vacation condo rental

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $589 / night

$4,123 / week

1 / 30

Ski condo to rent in Caribbean

Oranjestad condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $638 / night

$4,466 / week

1 / 30

Vacation condo in Caribbean

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $641 / night

$4,487 / week

1 / 30

Vacation home in Caribbean

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from $911 / night

$6,377 / week

1 / 26

Vacation villa in Caribbean

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from $1,662 / night

$11,634 / week

1 / 30

Villa rental in Caribbean

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,882 / night

$13,174 / week

1 / 30

Ski home to rent in Caribbean

George Town house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $562 / night

$3,934 / week

1 / 30

Vacation villa rental

Farmer's Hill villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $786 / night

$5,502 / week

1 / 30

Vacation home in Caribbean

Rincon house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

from $525 / night

$3,675 / week

1 / 29

Vacation villa rental

Rincon villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $376 / night

$2,632 / week

1 / 30

Vacation home in Caribbean

Michelson house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $608 / night

$4,256 / week

1 / 30

Vacation apartment in Caribbean

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $478 / night

$3,346 / week

1 / 30

Guadeloupe ski home to rent.

Le Moule house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $91 / night

$637 / week

1 / 30

Vacation home in Caribbean

Savaneta house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $960 / night

$6,720 / week

1 / 30

Vacation condo in Caribbean

Cruz Bay condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $607 / night

$4,249 / week

1 / 30

Ski condo to rent in Caribbean

Carolina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $217 / night

$1,519 / week

1 / 28

Ski condo to rent in Caribbean

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $678 / night

$4,746 / week

1 / 30

Caribbean Vacation condo rental

Nassau condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,243 / night

$8,701 / week

1 / 13

Home rental in Caribbean

Lajas house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $553 / night

$3,871 / week

1 / 25

Caribbean ski villa to rent.

Breakers villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $527 / night

$3,689 / week

1 / 30

Caribbean Vacation condo rental

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $413 / night

$2,891 / week

1 / 28

Caribbean Vacation condo rental

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $471 / night

$3,297 / week

1 / 30

Cottage rental in Caribbean

Coral Bay cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 / week

1 / 26

Caribbean ski condo to rent.

Aguadilla condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $179 / night

$1,253 / week

1 / 24

Ski villa to rent in Caribbean

Punta Cana villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

from $1,422 / night

$9,954 / week

1 / 30

Condo rental in Caribbean

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $303 / night

$2,121 / week

1 / 30

Vacation condo in Caribbean

Rockley condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $186 / night

$1,302 / week

1 / 30

Caribbean ski home to rent.

Leeward house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $348 / night

$2,436 / week

1 / 30

Vacation home in Caribbean

Rincon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from $647 / night

$4,529 / week

1 / 30

Vacation condo in Caribbean

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $448 / night

$3,136 / week

1 / 30

Caribbean Vacation condo rental

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $482 / night

$3,374 / week

1 / 30

Vacation condo in Caribbean

Carolina condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $185 / night

$1,295 / week

1 / 13

Ski apartment to rent in Puerto Rico

Carolina apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from $182 / night

$1,274 / week

1 / 19

Vacation villa in Caribbean

Cooper Jack Bay Settlement villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $613 / night

$4,291 / week

1 / 25

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