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Holiday Lettings
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> Villas and estates in Caribbean

Villas in Caribbean and Estates - Holiday Lettings - Holiday Rentals Caribbean

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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56,436 Holiday homes

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Martinique ski villa to rent.

Le Diamant villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £246 / night

£1,722 / week

1 / 30

U.S. Virgin Islands holiday condo rental

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £344 / night

£2,409 / week

1 / 30

Holiday home rental

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £632 / night

£4,422 / week

1 / 18

Holiday condo in Aruba

Oranjestad condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £287 / night

£2,008 / week

1 / 30

Holiday condo rental

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £330 / night

£2,310 / week

1 / 30

Condo rental in Caribbean

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £379 / night

£2,651 / week

1 / 30

Caribbean holiday condo rental

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £441 / night

£3,085 / week

1 / 30

Ski condo to rent in Caribbean

Oranjestad condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £512 / night

£3,580 / week

1 / 30

Caribbean ski condo to rent.

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £491 / night

£3,432 / week

1 / 30

Holiday apartment in Caribbean

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £572 / night

£4,004 / week

1 / 30

Ski villa to rent in Caribbean

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £1,306 / night

£9,140 / week

1 / 30

Holiday home in Caribbean

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £708 / night

£4,955 / week

1 / 26

Holiday villa rental

Farmer's Hill villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £565 / night

£3,954 / week

1 / 30

Ski home to rent in Caribbean

George Town house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from £442 / night

£3,091 / week

1 / 30

Holiday condo in Caribbean

Cruz Bay condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £501 / night

£3,503 / week

1 / 30

Villa rental in Caribbean

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,479 / night

£10,349 / week

1 / 30

Holiday home in Caribbean

Rincon house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

from £458 / night

£3,206 / week

1 / 29

Holiday home in Caribbean

Michelson house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £366 / night

£2,557 / week

1 / 30

Holiday villa rental

Rincon villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £291 / night

£2,035 / week

1 / 30

Puerto Rico ski apartment to rent.

Isla Verde apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £100 / night

£699 / week

1 / 22

Caribbean holiday condo rental

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £335 / night

£2,343 / week

1 / 28

Caribbean ski villa to rent.

Breakers villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £402 / night

£2,810 / week

1 / 30

Guadeloupe ski home to rent.

Le Moule house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £74 / night

£515 / week

1 / 30

Holiday home in Caribbean

Savaneta house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £850 / night

£5,950 / week

1 / 30

Ski condo to rent in Caribbean

Carolina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £194 / night

£1,353 / week

1 / 28

Caribbean holiday condo rental

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £297 / night

£2,079 / week

1 / 30

Caribbean holiday condo rental

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £390 / night

£2,728 / week

1 / 30

Caribbean holiday condo rental

Nassau condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £1,015 / night

£7,099 / week

1 / 13

Home rental in Caribbean

Lajas house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £435 / night

£3,041 / week

1 / 25

Cottage letting in Caribbean

Coral Bay cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £221 / night

£1,546 / week

1 / 26

Holiday villa in Caribbean

Cooper Jack Bay Settlement villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £483 / night

£3,377 / week

1 / 25

Caribbean ski home to rent.

Leeward house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £256 / night

£1,788 / week

1 / 30

Caribbean ski condo to rent.

Aguadilla condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £141 / night

£985 / week

1 / 24

Ski villa to rent in Caribbean

Punta Cana villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

from £982 / night

£6,874 / week

1 / 30

Holiday condo in Caribbean

Rockley condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £160 / night

£1,117 / week

1 / 30

Condo rental in Caribbean

Red Hook condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £234 / night

£1,639 / week

1 / 30

Holiday condo in Caribbean

Bajura condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £308 / night

£2,156 / week

1 / 30

Holiday condo in U.S. Virgin Islands

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £280 / night

£1,958 / week

1 / 30

Holiday apartment in Puerto Rico

Carolina apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £143 / night

£1,001 / week

1 / 19

Holiday home in Caribbean

Rincon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £520 / night

£3,635 / week

1 / 30

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Caribbean holidays

Turquoise ocean, sun-bleached sand, peach-gold sunsets and the most easy-going people on the planet… the Caribbean is every inch the perfect tropical paradise. Saint Lucia, Antigua, Dominica, Barbuda, Hispaniola and over 700 more islands are waiting to steal your heart.

Beachside Bliss

Awarding the title of ‘best beach in the Caribbean’ is like deciding which diamond in the Crown Jewels sparkles the most. It’s a nigh-on impossible, yet dazzling experience. Grand Cayman’s seven-mile paradise is a good place to start, with water as clear as glass, and the luxurious capital of George Town a stone’s throw away. Other Caribbean beach havens include Jamaica’s Montego Bay and virtually anywhere on Saint Martin island.

Secret Treasures

But the Caribbean isn’t all beaches and blue topaz seas. If you can drag yourself away from the sand on Puerto Rico, you’ll discover the tropical rainforest of El Yunque National Forest. Explorers who venture inland on most islands will be rewarded with secluded waterfalls, like Dunn’s River Falls in Ocho Rios, Jamaica.

Sub-Marine Spectacular

Snorkelling in the azure seas of the Caribbean is incredible, not least because of the vivid colours on display. Shoals of shimmering fish dart between coral reefs beneath the waves and when you come up for air, forests and palm trees cover the coasts. It’s like someone has turned up the colour saturation on your television. Head to Antigua’s Stingray City, a marine life petting zoo, for a hands-on experience you’ll never forget.

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