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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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41,569 Holiday homes

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Holiday villa in Martinique

Le Diamant villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £211 / night

£1,474 / week

1 / 30

U.S. Virgin Islands holiday condo rental

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £247 / night

£1,730 / week

1 / 30

Holiday studio rental

Red Hook studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £247 / night

£1,730 / week

1 / 30

Condo rental in Caribbean

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £358 / night

£2,507 / week

1 / 30

Aruba ski condo to rent.

Oranjestad condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £264 / night

£1,847 / week

1 / 30

Holiday home rental

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £630 / night

£4,406 / week

1 / 18

Puerto Rico ski home to rent.

Punta Santiago house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £309 / night

£2,161 / week

1 / 30

Caribbean holiday condo rental

Red Hook condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

from £233 / night

£1,629 / week

1 / 30

Holiday condo in Caribbean

Red Hook condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £317 / night

£2,214 / week

1 / 30

Caribbean holiday condo accommodation

Oranjestad condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £376 / night

£2,629 / week

1 / 30

Holiday home in Caribbean

San Juan house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £628 / night

£4,396 / week

1 / 26

Ski villa to rent in Caribbean

Montego Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £796 / night

£5,572 / week

1 / 30

Ski home to rent in Caribbean

George Town house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £433 / night

£3,028 / week

1 / 30

Holiday studio in Caribbean

Cruz Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £185 / night

£1,293 / week

1 / 30

Holiday villa rental

Farmer's Hill villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £528 / night

£3,693 / week

1 / 30

Villa rental in Caribbean

Montego Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,132 / night

£7,924 / week

1 / 30

Holiday villa rental

Rincon villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £272 / night

£1,900 / week

1 / 30

Holiday home in Caribbean

Rincon house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

from £331 / night

£2,315 / week

1 / 29

Holiday condo in Caribbean

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £299 / night

£2,092 / week

1 / 30

Holiday home in Caribbean

Michelson house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £289 / night

£2,022 / week

1 / 30

Puerto Rico ski studio to rent.

Isla Verde studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £97 / night

£676 / week

1 / 22

Caribbean holiday condo rental

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £274 / night

£1,916 / week

1 / 28

Holiday home in Guadeloupe

Le Moule house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £73 / night

£511 / week

1 / 30

Holiday home in Caribbean

Savaneta house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £717 / night

£5,018 / week

1 / 24

Ski condo to rent in Caribbean

Carolina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £159 / night

£1,107 / week

1 / 28

Cottage letting in Caribbean

Coral Bay cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

from £188 / night

£1,315 / week

1 / 26

Caribbean holiday condo rental

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £259 / night

£1,810 / week

1 / 30

Caribbean holiday condo rental

Nassau condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £836 / night

£5,848 / week

1 / 13

Home rental in Caribbean

Lajas house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £427 / night

£2,986 / week

1 / 25

Ski condo to rent in Caribbean

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £296 / night

£2,070 / week

1 / 30

Caribbean ski villa to rent.

Cooper Jack Bay Settlement villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £441 / night

£3,087 / week

1 / 25

Holiday condo in Caribbean

Rockley condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £156 / night

£1,091 / week

1 / 30

Caribbean ski home to rent.

Leeward house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £195 / night

£1,363 / week

1 / 30

Caribbean ski condo to rent.

Aguadilla condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £136 / night

£953 / week

1 / 24

Condo rental in Caribbean

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £206 / night

£1,442 / week

1 / 30

Caribbean holiday condo let

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £285 / night

£1,996 / week

1 / 30

Holiday condo in Caribbean

Bajura condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £290 / night

£2,028 / week

1 / 30

Caribbean ski villa to rent.

Breakers villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £341 / night

£2,384 / week

1 / 30

Holiday condo in U.S. Virgin Islands

Smith Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £223 / night

£1,560 / week

1 / 30

Holiday condo in Caribbean

Carolina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £144 / night

£1,006 / week

1 / 29

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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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