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Family Friendly Holidays in Cayman Islands - Holiday Lettings

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Home rental in Cayman Islands with swimming pool

South Town house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £162 / night

£1,130 / week

1 / 6

Villa accommodation in Cayman Islands

George Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £128 / night

£896 / week

1 / 11

Holiday home in West End

West End house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £138 / night

£1,261 / week

1 / 29

Holiday condo rental

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £185 / night

£1,021 / week

1 / 39

Home rental in Cayman Islands with swimming pool

West End house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

from £238 / night

£1,661 / week

1 / 18

Holiday apartment in Cayman Islands

Breakers apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £143 / night

£996 / week

1 / 18

Holiday home in Cayman Islands

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £280 / night

£1,958 / week

1 / 17

Holiday home in North Side

North Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £498 / night

£3,484 / week

1 / 24

Holiday home in Cayman Islands

East End house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £564 / night

£3,949 / week

1 / 22

Holiday home in Cayman Islands

Bodden Town house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £190 / night

£1,329 / week

1 / 18

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £261 / night

£1,825 / week

1 / 18

Holiday home in Cayman Islands

Rum Point house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 20

from £2,797 / night

£19,576 / week

1 / 51

Holiday home in Cayman Islands

Rum Point house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Perfect family getaway...!” We stayed at Cayman - Rum Point two years ago in a different villa...just as beautiful but incredibly windy. Two Rainbows is tucked away around the bend and it made all the difference in the world. We enjoyed our private beach without the bothersome wind. We are two families, with 5 kids under the age of 12, and we had the beach right at our own back door, without having to walk down a walkway, shallow smooth water, walking distance to Rum Points restaurant/bars/shops. We could sit on the back porch and watch the kids play - unlike others where the porch is elevated and you do not have a clear view of the beach. The villa accommodated us perfectly. Our best spring break trip yet...!

from £1,086 / night

£7,598 / week

1 / 26

Holiday home in North Side

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £375 / night

£2,621 / week

1 / 21

East End holiday home rental

East End house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £640 / night

£4,479 / week

1 / 31

Holiday home in Rum Point

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Great for groups/families!!” Reef Romance is like a second home to me. I stayed here first with girlfriends; then returned with our husbands. The house is spacious, inviting, and comfortable. It provides space for gatherings; and bedroom suites for privacy. The house is well equipped with amenities; fully-stocked kitchen, washer/dryer, linens, and even toys for the pool. The private beach is amazing! Each day is a new adventure of snorkeling, walking, and relaxing. I highly recommend staying at Reef Romance!

from £1,043 / night

£7,300 / week

1 / 19

Holiday apartment with shared pool in Rum Point

Rum Point apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Excellent Cayman Kai Condo” We've stayed in the Kaibo Phase II condos several times previously and Moonlight Kai did not disappoint. Maia was really easy to work with in setting everything up. We had one slight issue with the payment (nothing to do with Maia) which was easily cleared up with a quick visit to the rental management office two minutes away. The furnishings are very modern, the kitchen was equipped with everything we needed and having Kaibo right next door cannot be beat. All in all, if you're looking for the quieter side of Cayman but still close to the essentials then this condo will suit you perfectly. We'd definitely rent this unit again.

from £237 / night

£1,659 / week

1 / 24

Holiday home in Cayman Islands

Rum Point house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £754 / night

£5,276 / week

1 / 35

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 £403 / night

£2,821 / week

1 / 12

Holiday home in Cayman Islands

Rum Point house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Family Vacation” Parents/grandparents (us), three adult children, two with spouses, 8 year old twins, 5 year old and a 7 month old, all had own bedrooms and bathroom. All bedrooms are large as are the bathrooms There is a pack and play on site and plenty of sitting areas where people do not have to crowd together. The private beach is very large, the pool great for all. Easy driving to Rum Point where we snorkeled, hung out on beach and ate out. We had two cars and explored the whole island seeing the attractions and beaches, restaurants. Kitchen is well equipped and there is an outside grill. This is a go back to villa. The area is not crowded like 7 mile, yet easy to get to for the shopping on non cruise ship days. The villa is very clean and well equipped. We stayed the end of June and beginning of July and only had one partially rainy day. We came in two groups, and the NY group had a later leaving flight than our late morning flight home to D.C. the owner let our daughters, spouse and baby have a late check out since their flight did not leave until 4:00 p.m.

from £659 / night

£4,612 / week

1 / 32

Cayman Islands holiday home let

Rum Point house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Wow! What an amazing place” We spent a wonderful week at the Heritage house and couldn't be more pleased. We arrived at the appointed check in time and the ladies were just completing their cleaning process, they do a great job. The house is well appointed as far as cookery and basic essentials. Rum point is literally a 5 minute walk down the road. The food at the restaurant is excellent, the bartenders were very attentive and a heavy pour which is ideal. The kids enjoyed the beach but also utilized the pool almost everyday. The snorkeling off the back is excellent, we encountered sea turtles, a lovely barracuda and copious other sea life. We enjoyed meals at the lighthouse, kaibo upstairs ( excellent rum selections) also. Beware that when the cruise ships are in town Wednesday and Thursday when we were there things are a little hectic. I definitely advise enjoying stingray city and the barrier reef on days when the ships are not in port. The coral gardens is an excellent snorkel spot, the moray eel is amazing. All together we had an amazing visit, the house was perfect for us and we would definitely recommend it. Maybe I shouldn't say that so it's available the next time we come down. One item to note, definitely bring water shoes, lots of rocks off the back of the house, not an issue unless you don't have water shoes.

from £545 / night

£3,816 / week

1 / 19

Holiday condo in Bodden Town

Bodden Town condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £143 / night

£854 / week

1 / 15

Bodden Town holiday villa rental

Bodden Town villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,418 / night

£9,921 / week

1 / 33

Cayman Islands holiday home rental

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £782 / night

£5,475 / week

1 / 40

Cayman Islands holiday home rental

Gun Bay house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £1,086 / night

£7,598 / 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 £659 / night

£4,612 / 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 £522 / night

£3,650 / week

1 / 29

Holiday villa rental

North Side villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Villa Emmanuel” We loved the Villa and Cayman Villas were great. The only thing that would be an improvement for guests who are residents would be to be able to pick up and drop the keys off in Kaibo. It was an inconvenience to have to go out to avis, especially as the drive to Kaibo is already long. We appreciate most guests must fly in, but if you have local guests again this would greatly enhance the experience.

from £825 / night

£5,774 / week

1 / 31

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 £403 / night

£2,821 / week

1 / 26

Holiday home with shared pool in Cayman Islands

Rum Point house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £356 / night

£2,492 / week

1 / 42

Home rental in Little Cayman

Little Cayman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £375 / night

£2,516 - £3,180 / week

1 / 24

Rum Point holiday home rental

Rum Point house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £1,418 / night

£9,921 / week

1 / 29

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 £659 / night

£4,612 / week

1 / 24

Holiday home letting

Rum Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £470 / night

£3,285 / week

1 / 24

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 £327 / night

£2,290 / week

1 / 21

Holiday villa with swimming pool in Cayman Islands

Camana Bay villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £643 / night

£4,498 / week

1 / 16

Holiday apartment with shared pool in Cayman Islands

Seven Mile Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £1,756 / night

£12,292 / week

1 / 93

Cayman Islands holiday home rental

Old Man Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £404 / night

£2,824 / week

1 / 19

Holiday home in Rum Point

Rum Point house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £380 / night

£2,655 / week

1 / 19

Holiday home rental

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £375 / night

£2,621 / week

1 / 26

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