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

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217 Holiday homes

Home rental in Cayman Islands with swimming pool

South Town house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £153 / night

£1,070 / week

1 / 6

Holiday condo with shared pool in Cayman Islands

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £3,110 / night

£21,768 / week

1 / 7

Holiday home in Cayman Islands

East End house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £535 / night

£3,745 / week

1 / 22

Holiday apartment in Cayman Islands

Savannah apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £161 / night

£1,127 / week

1 / 13

Apartment rental in Seven Mile Beach with swimming pool

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £172 / night

£1,142 - £3,587 / week

1 / 30

Holiday home in Cayman Islands

Rum Point house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 20

from £5,260 / night

£36,815 / week

1 / 51

Holiday home in North Side

North Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £473 / night

£3,305 / week

1 / 24

Home accommodation in Cayman Islands

West Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £989 / night

£6,923 / week

1 / 20

Holiday villa with shared pool in Cayman Islands

Bodden Town villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £180 / night

£1,259 / week

1 / 26

Home rental in Cayman Islands with swimming pool

West End house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

from £248 / night

£1,731 / week

1 / 18

Rum Point holiday home rental

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £266 / night

£1,857 / week

1 / 24

Holiday home in Cayman Islands

North Side house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Impossible to put in one sentence...unless it's a run-on sentenc” This home was almost perfect for our family. I say "almost" because our 17 year-old grandson had to sleep on the sofa. And with 6 adult early-risers, his beauty sleep was interrupted. (the 2 teen-aged granddaughters got the twin beds upstairs) Other than that, the home was exceptionally wonderful. We brought all items recommended (detergent, TP, etc.,) but the home was well-stocked already. I really can't say enough about the home. Our daughter asked us all one evening what we liked best about the house, and we all said "everything!" Beautifully decorated. Great, well-equipped kitchen. Really appreciated the beach towels provided. And the deck. The beach was not perfect (lots of seaweed washed up on shore, and there was also some debris) but the snorkeling was very nice, and we enjoyed the cabana. The north side is windy, but after spending some time on 7 Mile Beach, we appreciated the breeze. And we loved the tranquility.

from £383 / night

£2,676 / week

1 / 12

Holiday home in North Side

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £356 / night

£2,486 / week

1 / 21

Holiday home in West Bay

West Bay house

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 22

from £1,255 / night

£8,779 / week

1 / 24

Holiday home in Cayman Islands

Rum Point house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £715 / night

£5,005 / week

1 / 35

Holiday villa accommodation

Cayman Brac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £162 / night

£1,079 - £1,268 / week

1 / 10

Cayman Islands holiday home rental

Old Man Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

“Awesome week with grown kids and grandkids” A very fine, high end home with a well equipped kitchen and very comfortable bedrooms. The layout with 5 bedrooms all with ensuite baths (including the cottage) was ideal for my wife and I, our three adult children, their spouses, plus 3 grandchildren. Everybody had their own space plus we shared the large, screened deck with heated swimming pool, comfortable living area, and large dining area for eating and playing games. Being on the north side it is remote and the beach is not for swimming but we knew that going in and it was fine for us. When we did want to swim in the ocean we took a short drive to Rum Point or a longer drive to Seven Mile beach.

from £715 / night

£5,003 / week

1 / 38

Rum Point holiday home rental

Rum Point house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £1,479 / night

£10,353 / week

1 / 27

Cayman Islands holiday home rental

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £742 / night

£5,192 / week

1 / 40

Holiday home in Cayman Islands

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £356 / night

£2,487 / week

1 / 29

Holiday home in Cayman Islands

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Place” Loved Sea Cove. Great location, a walk to Rum Point and Kaibo Yacht Club. Beautiful sunsets. No pool, but it was okay without it. Thought the house was lovely.

from £311 / night

£2,172 / week

1 / 21

Cayman Islands holiday home rental

Gun Bay house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £1,030 / night

£7,206 / week

1 / 36

Holiday home rental

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Fantastic Experience & a view that words cannot describe!” I wanted to let you know how pleased we were with our Cayman beachside villa! We stayed in the Fingertip Villa. Our villa was very clean and the amenities inside the villa (towels, comfort of beds, cleanliness of villa) were wonderful! We couldn't have been more satisfied! We were also very impressed by the villa manager Chloe Campbell! She stopped by the day after we arrived to welcome us and answer all of our questions. We also saw her another day. She was very friendly and professional! The location and views from the Fingertip Villa are out of this world - beauty like we had never seen before ! We hope to come back again someday! Thanks to everyone involved This is the first time any of us (3 couples) had ever traveled outside of the Untied States so we especially appreciated the help everyone gave us in planning and organizing our trip.

from £625 / night

£4,376 / week

1 / 22

Home rental in Cayman Islands

Old Man Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“The best of the best!!!” Just what we needed! A beautiful home, perfect location to calm our tired souls and mend our weary bodies and every amenity and convenience you could possibly ask for. Villa Caymanas is truly a dream come true, a private paradise on a "grand" little island. We have had the time of our lives. No where could have been as perfect as Villa Caymanas. The owners have thought of everything... We have had so much fun; will never forget and hope to return very soon to Villa Caymanas.

from £495 / night

£3,462 / week

1 / 29

Holiday villa in Seven Mile Beach

Seven Mile Beach villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £1,079 / night

£7,552 / week

1 / 15

Holiday home in Cayman Islands

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing as always” We try to go to Grand Cayman every year and we always stay at this house. We absolutely love it! Our favorite part is that the pool faces the ocean and there is always a nice wind blowing. Of course the house is nicely decorated and has all the amenities we need. I highly recommend Cayman Dream.

from £382 / night

£2,675 / week

1 / 26

Holiday home rental

West Bay house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

“Money I Would Eagerly Spend again” Sitting under Tiki House's bouganviellia covered trellis is the ultimate way to enjoy a morning cup of coffee or an evening cocktail. With the beach just across the road, snorkeling became part of our daily routine as did watching the sun set itself into the turquoise waters. Good Restaurants, wonderful shopping and many activities abound if so desired. Tiki House is very clean. I was pleased with the kitchen and the layout of the house as two of the bedrooms are upstairs. Tiki House certainly has a place in our hearts.

from £450 / night

£3,147 / week

1 / 20

Holiday home in Cayman Islands

Savannah house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from £900 / night

£6,296 / week

1 / 39

Home rental in Little Cayman

Little Cayman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £356 / night

£2,383 - £3,012 / week

1 / 24

Cayman Brac holiday villa rental

Cayman Brac villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 8

from £320 / night

£2,486 - £3,116 / week

1 / 27

Holiday apartment in Cayman Brac

Cayman Brac apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £135 / night

£899 / week

1 / 9

Holiday home in Rum Point

Rum Point house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great Family Vacation” The house was wonderful, the location was excellent! Quiet! And the bio illumination was sooo cool! We all had a great time!

from £715 / night

£5,003 / week

1 / 38

Holiday apartment in Cayman Islands

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £539 / night

£3,770 / week

1 / 8

Holiday home letting

Rum Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £445 / night

£3,115 / week

1 / 22

Apartment rental in Cayman Islands with shared pool

West Bay apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,798 / night

£12,580 / week

1 / 55

Bodden Town holiday villa rental

Bodden Town villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,165 / night

£8,150 / week

1 / 35

Cayman Islands holiday home rental

West End house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £302 / night

£2,109 / week

1 / 10

Holiday home with swimming pool in Cayman Islands

West End house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £302 / night

£2,109 / week

1 / 12

Holiday home in Rum Point

Rum Point house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £266 / night

£1,857 / week

1 / 19

Holiday home rental

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £356 / night

£2,486 / week

1 / 26

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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.

Top Destination reviews

Just Chillin
Beautiful!!

The place was beautiful everything were in order and the property is central with a lovely stretch of beach. The host Dianne was fantastic she went above and beyond to make sure we were comfortable. I definitely recommend this property and I already booked to go back in September. Dianne, thank you, thank you, you certainly made our vacation easy and unforgettable.see more
Great Location & Value! 7mile Beach Condo next to a Resort Hotel!
Very good stay - Livia was very attentive and full of suggestions of places to eat/go

On 7 Mile beach - I loved the early morning walks and later afternoon walks along one of the most beautiful beaches. Apartment was good with plenty of space and facilities … see more
2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2
Fantastic apartment

Very comfortable and well equipped apartment. Plenty of space. Balcony was meshed so no problems with insects. The recently upgraded white goods make this apartment even better. Lovely location in a quieter part of the island but still easy to access. Kayak and bikes were an added bonus. The proximity to starfish point, Rum Point and the bio bay make vista easy. The yacht club restaurant and bar next door offered a good selection of food and drink- the Tuesday evening bbq worth a visit. The only disappointment was the beach/sea in the bay is not really for swimming due to jelly fish, boat traffic and the ‘lagoon smell’ - this isn’t the open sea. Thankfully the lovely swimming pool made up for this. Had a fantastic holiday and would love to return.see more

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