Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Best Caribbean Villas on Holiday Lettings - Vacation rentals

All filters

Filters

56,598 Vacation rentals

Martinique ski villa to rent.

Le Diamant villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $309 / night

$2,163 / 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 $365 / night

$2,555 / week

1 / 30

Vacation condo rental

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from $375 / night

$2,625 / week

1 / 30

Condo rental in Caribbean

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $452 / night

$3,164 / 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 $522 / night

$3,654 / week

1 / 30

Ski condo to rent in Caribbean

Oranjestad condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $651 / night

$4,557 / week

1 / 30

Vacation condo in Caribbean

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $534 / night

$3,738 / week

1 / 30

Vacation apartment in Caribbean

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $548 / night

$3,836 / week

1 / 30

Ski villa to rent in Caribbean

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from $1,662 / night

$11,634 / week

1 / 30

Vacation home in Caribbean

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from $872 / night

$6,104 / week

1 / 26

Vacation villa rental

Farmer's Hill villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $719 / night

$5,033 / week

1 / 30

Vacation condo in Caribbean

Cruz Bay condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $692 / night

$4,844 / week

1 / 30

Caribbean Vacation home accommodation

George Town house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $562 / night

$3,934 / week

1 / 30

Villa rental in Caribbean

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,880 / night

$13,160 / week

1 / 30

Vacation home in Caribbean

Rincon house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

from $598 / night

$4,186 / week

1 / 29

Vacation home in Caribbean

Michelson house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $465 / night

$3,255 / week

1 / 30

Vacation villa rental

Rincon villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $370 / night

$2,590 / week

1 / 30

Caribbean Vacation condo rental

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $453 / night

$3,171 / week

1 / 28

Guadeloupe ski home to rent.

Le Moule house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $93 / night

$651 / week

1 / 30

Caribbean ski villa to rent.

Breakers villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $511 / night

$3,577 / week

1 / 30

Vacation home in Caribbean

Savaneta house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $1,082 / night

$7,574 / week

1 / 30

Ski condo to rent in Caribbean

Carolina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $246 / night

$1,722 / week

1 / 28

Caribbean Vacation condo rental

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $378 / night

$2,646 / week

1 / 30

Caribbean Vacation condo rental

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $496 / night

$3,472 / week

1 / 30

Caribbean Vacation condo rental

Nassau condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,273 / night

$8,911 / 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.

Cooper Jack Bay Settlement villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $614 / night

$4,298 / week

1 / 25

Cottage rental in Caribbean

Coral Bay cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $281 / night

$1,967 / week

1 / 26

Caribbean ski home to rent.

Leeward house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $325 / night

$2,275 / week

1 / 30

Caribbean ski condo to rent.

Aguadilla condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $179 / night

$1,253 / week

1 / 24

Villa rental in Caribbean

Punta Cana villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

from $1,250 / night

$8,750 / 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 $203 / night

$1,421 / week

1 / 30

Vacation condo in Caribbean

Bajura condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $392 / night

$2,744 / week

1 / 30

Vacation condo in U.S. Virgin Islands

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $279 / night

$1,953 / week

1 / 30

Vacation apartment in Puerto Rico

Carolina apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from $172 / night

$1,204 / week

1 / 19

Vacation condo in Caribbean

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $453 / night

$3,171 / week

1 / 30

Vacation condo rental

Cruz Bay condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $900 / night

$6,300 / week

1 / 30

×

Also consider