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Watersports Holidays in Cayman Islands - Holiday Lettings

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43 properties with watersports onsite or nearby

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Holiday villa accommodation

Cayman Brac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £167 / night

£1,111 - £1,305 / week

1 / 10

Cayman Brac holiday villa rental

Cayman Brac villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 8

from £329 / night

£2,560 - £3,207 / week

1 / 27

Holiday apartment with golf nearby in Seven Mile Beach

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £310 / night

£1,944 - £2,657 / week

1 / 47

Holiday villa in Little Cayman

Little Cayman villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £463 / night

£3,240 / week

1 / 23

Holiday villa with shared pool in Cayman Islands

Little Cayman villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £463 / night

£3,240 / week

1 / 25

Holiday condo rental

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £250 / night

£1,750 / week

1 / 23

Holiday apartment accommodation

Bodden Town apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £278 / night

£1,944 / week

1 / 13

Holiday villa in Cayman Islands

Rum Point villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 12

from £647 / night

£4,529 / week

1 / 38

Holiday townhouse with shared pool in Cayman Islands

Cayman Brac townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £186 / night

£1,296 / week

1 / 9

Cayman Islands holiday apartment rental

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Home away from home” What a wonderful spot, peaceful,quiet and secluded away from busy seven mile beach. This unit has all the amenities of home, plus what you may need for the beach. We used the cooler for lunches on the go on a couple of days when we went diving in the West end, so very handy. The pool outside the condo with the ocean only 50 yards away was like walking out into paradise every morning. We enjoyed the Lanai and would have supper while listening to the ocean. The unit and property is well groomed and looked after. My thanks to Bob as well for being so attentive to detail in terms of the condo beds for comfort and amenities available. We were well informed by Bob in regards to details about the rental, and who to call if there were issues. We had detailed information about things to do, restaurants , etc. We are hoping to be able to return again in 2012 and will definitely be renting this unit again!

from £162 / night

£2,365 - £2,495 / week

1 / 11

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!

from £227 / night

£1,588 - £2,236 / week

1 / 21

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)

from £371 / night

£2,592 / week

1 / 37

Holiday condo with shared pool, golf nearby in Cayman Islands

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Best Family Vacation Ever!” We came to Grand Cayman to scuba dive as a family. Our condo was a wonderful place to relax after our dive trips because of its proximity to the beach and the pool. Boggy Sands Beach Club is within walking distance of some great local food. Heritage Kitchen, ALFresco, and Calico Bar. The owner Morne Botes was attentive to all of our needs and great to work with. We highly recommend this place and hope to return very soon.

from £1,851 / night

£12,952 / week

1 / 43

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!

from £162 / night

£1,134 / week

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Apartment rental in Cayman Islands with swimming pool

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £320 / night

£2,236 / week

1 / 20

Home rental in Cayman Islands with shared pool

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £425 / night

£2,974 / week

1 / 30

Rum Point holiday home rental

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £425 / night

£2,974 / week

1 / 31

Cayman Islands holiday condo rental

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £3,054 / night

£21,374 / week

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Seven Mile Beach holiday condo rental

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £320 / night

£2,236 / week

1 / 18

Holiday apartment rental

Savannah apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £218 / night

£1,294 / week

1 / 11

Holiday home with swimming pool in Cayman Brac

Cayman Brac house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £232 / night

£1,666 - £2,314 / week

1 / 15

Holiday villa with shared pool in Rum Point

Rum Point villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £555 / night

£3,881 / week

1 / 13

Cayman Islands holiday home rental

West Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £278 / night

£1,852 / week

1 / 24

Holiday home with shared pool in Cayman Islands

Rum Point house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £378 / night

£2,644 / week

1 / 46

Home rental in Cayman Islands

South Town house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £324 / night

£2,041 - £2,333 / week

1 / 29

Holiday home in North Side

North Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £366 / night

£2,129 / week

1 / 13

Holiday apartment in Bodden Town

Bodden Town apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £116 / night

£810 / week

1 / 15

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!

from £366 / night

£2,453 / week

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Cayman Islands holiday condo rental

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,851 / night

£12,952 / week

1 / 34

Holiday condo with shared pool in Cayman Islands

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £301 / night

£1,713 / week

1 / 13

Rum Point holiday home rental

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £555 / night

£3,881 / week

1 / 37

Holiday condo with shared pool in Cayman Islands

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £370 / night

£2,585 / week

1 / 27

Apartment rental in Rum Point with shared pool

Rum Point apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Our Cayman vacation” We had a wonderful vacation to the Cayman Islands. The condo was beautiful and had all the comforts of home. We made breakfast in the morning and ate on the lanai with a beautiful view of the ocean. A couple days we turned the air conditioning off and open the windows. There was a great breeze and we could hear the ocean and palms. It was wonderful to go to sleep with the sounds of the ocean and wake up to the ocean. We loved the location. We stayed 2 nights in Seven Mile and the crowds of people was enough for us. The area the condo was in was away from all the crowds of tourist. On a return trip we decided we would rather stay at Rum Point, away from the crowds. The beach was great but water shoes are a must. We had tropical fish and stringray swim around us while just wading in the ocean. My husband and brother-in-law did some snorkeling and said there was plenty to see. The condo is fully equipped with everything you need. Not that we spent alot of time in the condo, mainly to sleep and eat. We had 4 adults in the condo and we were comfortable. What we like best is we were away from the crowds which made for a truly relaxing vacation!! We are already talking about going back!!!

from £227 / night

£1,361 - £2,361 / week

1 / 70

Condo rental in Cayman Islands with golf nearby

Seven Mile Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £459 / night

£3,207 / week

1 / 38

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £278 / night

£1,944 / week

1 / 18

Holiday villa rental

Little Cayman villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £240 / night

£1,678 / week

1 / 21

Holiday home with shared pool in Cayman Islands

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £425 / night

£2,974 / week

1 / 30

Cayman Islands holiday condo rental

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Sunset Cove” Beautiful condo; Situated on 7 mile beach. As a first timer to Grand Cayman, the trip was booked solely on the condo as viewed online. We were not disappointed. Bill Newton, owner, has equipped the condo with all the 'tech' savvy items you could want. Alexa {?} controls the fan, lights, etc. Huge TV made teens happy...... The hot tub, pool with swim up bar and grill are great. The rock protected cove with access to the open water allows for snorkeling on a nearby reef. The city buses run all day--you just flag one down--pay $2.50 US and they let you off at your destination.

from £278 / night

£1,944 / week

1 / 49

Holiday apartment with swimming pool in Cayman Islands

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £320 / night

£2,236 / week

1 / 21

Holiday condo with shared pool, golf nearby in Cayman Islands

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £509 / night

£2,388 / week

1 / 21

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