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Family Friendly Holidays in Cayman Islands - Holiday Lettings

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228 family friendly properties

Rum Point holiday home rental

Rum Point house

3 bedrooms • 3 bathrooms • sleeps 8

from £373 / night

£2,608 / week

1 / 31

Rum Point holiday home rental

Rum Point house

3 bedrooms • 3 bathrooms • sleeps 8

1 review

from £487 / night

£3,404 / week

1 / 37

Holiday guest house in Seven Mile Beach

Seven Mile Beach guest house

2 bedrooms • 2 bathrooms • sleeps 6

11 reviews

from £166 / night

£988 - £2,150 / week

1 / 21

Home rental in Cayman Islands with shared pool

Rum Point house

3 bedrooms • 3 bathrooms • sleeps 8

from £381 / night

£2,666 / week

1 / 30

Holiday condo with shared pool in Cayman Islands

Seven Mile Beach condo

4 bedrooms • 5 bathrooms • sleeps 10

14 reviews

from £882 / night

£6,173 - £19,128 / week

1 / 29

Holiday villa with shared pool in Rum Point

Rum Point villa

3 bedrooms • 3 bathrooms • sleeps 8

1 review

from £487 / night

£3,404 / week

1 / 13

Holiday home with shared pool in Cayman Islands

Rum Point house

3 bedrooms • 3 bathrooms • sleeps 8

from £373 / night

£2,608 / week

1 / 30

Holiday apartment in Cayman Islands

Bodden Town apartment

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from £84 / night

£583 / week

1 / 16

Holiday home in Bodden Town

Bodden Town house

2 bedrooms • 2 bathrooms • sleeps 4

from £83 / night

£579 / week

1 / 21

Holiday apartment in Cayman Islands

Bodden Town apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £95 / night

£659 / week

1 / 18

Holiday apartment in Cayman Islands

Breakers apartment

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from £75 / night

£525 / week

1 / 18

Holiday villa rental

Seven Mile Beach villa

2 bedrooms • 2 bathrooms • sleeps 4

2 reviews

from £1,819 / night

£12,732 - £20,370 / week

1 / 37

Holiday villa with shared pool in Seven Mile Beach

Seven Mile Beach villa

4 bedrooms • 3 bathrooms • sleeps 10

from £942 / night

£6,588 / week

1 / 15

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.

41 reviews

from £188 / night

£1,312 / week

1 / 27

Holiday home in Cayman Islands

East End house

2 bedrooms • 2 bathrooms • sleeps 6

“Paradise in the Caymans” If your idea of vacation is relaxing on a beach away from the maddening crowds then this is the place. This totally accessible cottage steps from a private beach was an amazing find. Newly remodeled with a gorgeous decor, comfortable beds, dishwasher, washer and dryer and walk-in shower, our every need was met. Cathy and Jerry made sure we felt right at home. The house was nicely stocked with towels, soap, shampoo and laundry detergent. A car is a must if you want to explore and driving was easy on the East End. I wish we had stayed two weeks!

20 reviews

from £209 / night

£1,458 / week

1 / 26

Cayman Islands holiday apartment rental

Seven Mile Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

11 reviews

from £249 / night

£1,744 / week

1 / 39

Cayman Islands holiday home rental

Rum Point house

5 bedrooms • 5 bathrooms • sleeps 12

1 review

from £646 / night

£4,519 / week

1 / 40

Holiday home in Rum Point

Rum Point house

2 bedrooms • 3 bathrooms • sleeps 4

from £334 / night

£2,333 / week

1 / 19

Holiday home in Cayman Islands

Little Cayman house

3 bedrooms • 3 bathrooms • sleeps 7

1 review

from £659 / night

£4,612 / week

1 / 8

Holiday apartment with shared pool in Cayman Islands

West Bay apartment

1 bedroom • 1 bathroom • sleeps 4

16 reviews

from £188 / night

£1,316 / week

1 / 17

Holiday home in North Side

North Side house

2 bedrooms • 2 bathrooms • sleeps 5

from £329 / night

£2,304 / week

1 / 21

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

2 bedrooms • 2 bathrooms • sleeps 6

5 reviews

from £229 / night

£1,604 / week

1 / 18

Rum Point holiday apartment rental

Rum Point apartment

2 bedrooms • 2 bathrooms • sleeps 4

3 reviews

from £188 / night

£1,312 / week

1 / 17

Holiday apartment with swimming pool in Cayman Islands

North Side apartment

2 bedrooms • 2 bathrooms • sleeps 6

“Absolutely amazing!” We recently had the pleasure of staying for 9 nights in the Mid-Winter Night's Dream condo on the north side of Grand Cayman. It was absolutely amazing! Dan was very easy to deal with, provided us a lot of tips and information about Grand Cayman and it was just a great experience. Everything we could possibly need was right there at the condo. We ate quite a few meals there and they had everything we needed to cook and grill. It was super clean and bright. View of the ocean right outside the master bedroom couldn't be beat...going to sleep with the sounds of the waves hitting the shore made for some amazing full night's sleep. Breakfast out on the lanai every morning. The pool was great! It felt wonderful after a day of snorkeling or just a first thing in the morning dip. Having the ocean right out our door was pretty amazing also. Snorkeling right there when the water was a little less wavy led to some nice adventures. They even have the snorkel gear and coolers for you for all day adventures! Being on the north side gave us a great opportunity to be away from the noise and commercialism of Seven Mile Beach and truly let the sun soak into our bones and relax. We still were only a 45 min drive to that side when we wanted to be. And it's only that long because you have to drive 30mph a lot of the way...which gives you time to really look around and admire the view! Definitely rent a car, there is plenty of space at the condo and it will afford you the opportunity to get to all the different parts of the island to check out all the amazing snorkeling spots. I will definitely stay here again!! You couldn't ask for more!

28 reviews

from £182 / night

£1,269 - £1,846 / week

1 / 21

Cayman Brac holiday villa rental

Cayman Brac villa

3 bedrooms • 5 bathrooms • sleeps 8

8 reviews

from £291 / night

£2,304 - £2,887 / week

1 / 30

Cayman Islands holiday cottage rental

Cayman Brac cottage

1 bedroom • 1 bathroom • sleeps 3

“Back to the Brac” We loved our time at Cayman Cottage on the Brac! This was our second trip to the Cottage and it was as wonderful as we remembered! The cottage has its own private, gorgeous beach that we drank coffee on early in the morning, snorkeled and sunned on in the afternoons and watched the beautiful sunsets each evening! It is clean, well maintained and comfortable. The owner is friendly and pleasant, accommodating any requests or questions we had. We walked to one of three nice restaurants most evenings, for delicious seafood or local island specialties. The island is very safe and the local people are friendly. We walked the island exploring each day and never had a minute of apprehension. We highly recommend Cayman Cottage for your taste of Paradise!

28 reviews

from £124 / night

£863 / week

1 / 37

Holiday villa in Cayman Islands

Rum Point villa

3 bedrooms • 2 bathrooms • sleeps 6

5 reviews

from £164 / night

£1,142 / week

1 / 24

Holiday apartment in Cayman Islands

Cayman Brac apartment

2 bedrooms • 2 bathrooms • sleeps 4

“Charming seaside cottage” Excellent location for the best snorkeling on island, quiet,private and on very low use back road perfect for morning and evening walks.(watch for the night herons) Rental is clean,owner truly a pleasure to work with. Safe area, close to fascinating museum and grocery store. Rates best on island.

5 reviews

from £124 / night

£868 / week

1 / 5

Holiday villa in Cayman Islands

North Side villa

3 bedrooms • 2 bathrooms • sleeps 6

“Escape from Brutal Chicago Winter - Vacation in Paridise” This is a very well maintained property with comfortable, up-to-date furnishings. The view is fantastic, and just as pictured. Plenty of dinnerware and cookware were provided, as well. We spent most of our time between Rum Point and at this lovely villa...just lounging, reading and enjoying the wonderful Caribbean sun. If you are looking for "action" on a daily basis this may not be your place, but if you value a knock-out view, relaxation, and privacy, this villa on the "quiet" side of the island is perfect. One trip to 7 Mile Beach and Georgetown was all we needed and were grateful to get back to real island living. Frank is easy to work with and quick to respond to questions and comments. Tukka, Lighthouse, Kaibo, and Over the Edge restaurants are nearby as well as dining at Rum Point. All very good. A small grocery store called Chisholm's is a few minutes away for everyday items. Fosters Express on the east end about 10 minutes away is also handy. For more serious shopping, Hurleys and a larger Foster's are about 30 minutes away. They stock everything you might get in the us. All in all...after a brutal winter here in the Chicago area, this was a slice of heaven. I would not hesitate to recommend this villa. Thank you Frank and Del for sharing!

21 reviews

from £320 / night

£2,143 - £3,275 / week

1 / 18

Holiday apartment in Cayman Brac

Cayman Brac apartment

1 bedroom • 1 bathroom • sleeps 2

7 reviews

from £107 / night

£747 / week

1 / 7

Holiday home with shared pool in Cayman Islands

Rum Point house

2 bedrooms • 3 bathrooms • sleeps 4

“Simple pleasures in an amazing setting.” Dear Janice and Mike We're writing this email to let you know how much we enjoyed our visit to Starboard Kai at the beginning of May. You have refurbished the house beautifully - you must be very proud of it. It certainly is very easy 'island living.' It was immaculately clean with high quality towels/linens. The wi-fi was fast and dependable.The master bed must be the most comfortable on Grand Cayman. Outside, the pool and grounds are conscientiously maintained to a high level. We loved the position of the house just across from Rum Point but we were never disturbed by noise from the road or 'over the road'. There are lots of things to keep you busy as have been detailed by the other reviews here. Our favourites were a) cycling down to Starfish Point each day for an early morning swim when there's no-one else about and b) taking a few steps across the road to the Rum Point Wreck Bar at around 6pm, buying a Rum Point Sunset (cocktail) and sitting in the peace and quiet watching the sun go down. Simple pleasures........ Your house manager Mitzie was off the island at the time of our visit but Sharon popped by on the first morning to see if we were OK. As it happened, just as she came by, we were struggling (and failing!) to pump up the rear tyres of both the bikes which had been left deflated by previous tenants. They needed more work on them than just the pump so Sharon took them away to have them fixed but managed to source two bikes for us from elsewhere. What wonderful service. Please pass on our thanks to her if you see her. Our week passed by very quickly with no further problems and we were sorry to leave. We would have no hesitation in recommending Starboard Kai to others. Helen and Chris (UK)

26 reviews

from £334 / night

£2,333 / week

1 / 37

Villa accommodation in Cayman Islands

West End villa

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from £121 / night

£846 / week

1 / 24

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.

14 reviews

from £459 / night

£3,207 / week

1 / 29

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...!

5 reviews

from £833 / night

£5,831 / week

1 / 26

Holiday apartment with shared pool in Seven Mile Beach

Seven Mile Beach apartment

4 bedrooms • 5 bathrooms • sleeps 10

5 reviews

from £2,471 / night

£17,297 / week

1 / 37

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.

14 reviews

from £479 / night

£3,353 / week

1 / 19

Home rental in West End with swimming pool

West End house

3 bedrooms • 2 bathrooms • sleeps 6

2 reviews

from £163 / night

£1,137 / week

1 / 22

Holiday villa with shared pool in Cayman Islands

Camana Bay villa

3 bedrooms • 3 bathrooms • sleeps 6

from £190 / night

£1,324 / week

1 / 25

Villa accommodation in Cayman Islands

George Town villa

1 bedroom • 1 bathroom • sleeps 2

from £113 / night

£788 / week

1 / 11

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.

25 reviews

from £334 / night

£1,750 - £5,831 / week

1 / 102

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