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Holiday Lettings
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> Caribbean
> Houses and villas in Cayman Islands

Houses in Cayman Islands and Villas - Holiday Lettings - Holiday Rentals Cayman Islands

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£1 £750 -

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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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897 Holiday homes

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Cayman Islands holiday condo rental

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £399 / night

£2,793 / week

1 / 30

Cayman Islands ski villa to rent.

Breakers villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £386 / night

£2,699 / week

1 / 30

Ski home to rent in Rum Point

Rum Point house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £522 / night

£3,650 / week

1 / 30

Cayman Islands ski condo to rent.

North Side condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £439 / night

£3,067 / week

1 / 30

Cayman Islands ski condo to rent.

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £869 / night

£6,079 / week

1 / 30

Condo rental in Cayman Islands

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £439 / night

£3,067 / week

1 / 30

Cayman Islands holiday condo accommodation

Seven Mile Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £391 / night

£2,738 / week

1 / 30

Holiday condo in George Town

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £325 / night

£2,276 / week

1 / 30

Holiday condo in Cayman Islands

Rum Point condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £336 / night

£2,347 / week

1 / 30

Holiday home rental

Stake Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £343 / night

£2,397 / week

1 / 22

Cayman Islands holiday condo rental

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £530 / night

£3,705 / week

1 / 30

Cayman Islands holiday condo rental

George Town condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £335 / night

£2,342 / week

1 / 22

Ski condo to rent in Cayman Islands

Seven Mile Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £462 / night

£3,232 / week

1 / 30

Holiday condo rental

Rum Point condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £444 / night

£3,106 / week

1 / 29

Holiday condo in West Bay

West Bay condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

from £480 / night

£3,359 / week

1 / 30

Holiday villa in Cayman Islands

George Town villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

from £2,966 / night

£20,760 / week

1 / 30

Cayman Islands ski condo to rent.

George Town condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £665 / night

£4,656 / week

1 / 20

Home rental in Cayman Islands

North Side house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £549 / night

£3,842 / week

1 / 30

Condo rental in Cayman Islands

Rum Point condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £222 / night

£1,550 / week

1 / 19

Holiday condo in Cayman Islands

West Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £512 / night

£3,579 / week

1 / 16

Holiday cottage in Cayman Islands

West End cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £138 / night

£962 / week

1 / 30

Holiday condo in Rum Point

Rum Point condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £217 / night

£1,517 / week

1 / 22

Ski condo to rent in Cayman Islands

George Town condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £786 / night

£5,502 / week

1 / 28

George Town ski condo to rent.

George Town condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £507 / night

£3,546 / week

1 / 30

Holiday condo rental

George Town condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £720 / night

£5,041 / week

1 / 30

Ski condo to rent in Camana Bay

Camana Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £748 / night

£5,233 / week

1 / 26

Holiday apartment in Cayman Islands

Rum Point apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £327 / night

£2,287 / week

1 / 30

Holiday cottage in Cayman Islands

Rum Point cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £417 / night

£2,919 / week

1 / 28

Ski villa to rent in Cayman Islands

North Side villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £324 / night

£2,265 / week

1 / 29

Ski condo to rent in Cayman Islands

Bodden Town condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £248 / night

£1,732 / week

1 / 30

Cayman Islands ski home to rent.

Rum Point house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £424 / night

£2,968 / week

1 / 30

Holiday condo in Cayman Islands

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £212 / night

£1,484 / week

1 / 30

Cayman Islands holiday condo accommodation

Rum Point condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £342 / night

£2,391 / week

1 / 19

Holiday condo letting

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £346 / night

£2,419 / week

1 / 30

Holiday condo in Rum Point

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £380 / night

£2,655 / week

1 / 29

Holiday villa in Cayman Islands

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £436 / night

£3,051 / week

1 / 30

Ski condo to rent in Cayman Islands

West Bay condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £302 / night

£2,111 / week

1 / 30

Holiday condo in Cayman Islands

Seven Mile Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £644 / night

£4,507 / week

1 / 30

Holiday condo in Cayman Islands

George Town condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £787 / night

£5,508 / week

1 / 30

Holiday condo in Cayman Islands

George Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £488 / night

£3,414 / week

1 / 30

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Cayman Islands holidays

The Cayman Islands are a British protectorate and are considered one of the most exclusive destinations in the Caribbean. Famous for their stunning natural beauty, the Cayman Islands have a tropical marine climate, making for warm and rainy summers and dry, mild winters. Most visitors elect to come here between October and April to escape the cold weather of the northern climates and take advantage of the Caymans' celebrated beauty.

Some of the major attractions and activities in the Cayman Islands include:

  • The Sister Islands: While Grand Cayman dominates most visitors' itineraries, the so-called "Sister Islands" of Little Cayman and Cayman Brac are perfect for those seeking a quieter, more private holiday.
  • George Town: The islands' capital city, George Town has an engaging and fascinating history, and it is well worth taking a tour of the city's many sights and points of interest.
  • Seven Mile Beach: Located on Grand Cayman, Seven Mile Beach is one of the most-developed corners of the Cayman Islands. Stroll the boardwalks, relax at a beachfront bar and take advantage of the excellent restaurants and lively nightlife. This area is the perfect setting for Cayman Islands weddings and Cayman Islands honeymoons.
  • Deep-sea diving: With crystal clear waters and mysterious coral reefs, the Cayman Islands offer some of the best scuba diving in the world. Diving enthusiasts from all over the globe come here in search of the ultimate experience.
  • Golf: Cayman Islands golf courses rank amongst the best in the Caribbean, and the weather is always perfect for teeing off. Club and equipment rentals are widely available and affordable, so you don't have to worry about lugging along your own gear.

Instead of cramping into a hotel room, relax in style in your very own holiday rental. A beachfront villa, a condo in George Town or an apartment on the coast makes the ideal alternative to traditional accommodations at affordable prices.

The islands lie less than 100 miles to the south of Cuba, and are also perfectly situated to continue your journey in Puerto Rico. As a popular port of call, it's also easy to get from the Cayman Islands to the U.S. and British Virgin Islands and many other Caribbean nations.

Also consider