Watersports Holidays in Cayman Islands - Holiday Lettings

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148 properties with watersports onsite or nearby

Rum Point holiday home rental

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Water sports

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from £229 / night

£1,600 / week

Rum Point holiday home rental

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

1

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from £264 / night

£1,847 / week

Holiday condo with shared pool in Cayman Islands

Seven Mile Beach condo

4 bedrooms / 5 bathrooms / sleeps 10

13

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from £694 / night

£4,854 - £14,639 / week

Holiday guest house in Seven Mile Beach

Seven Mile Beach guest house

2 bedrooms / 2 bathrooms / sleeps 6

9

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from £178 / night

£972 - £2,308 / week

Home rental in Cayman Islands with shared pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

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from £230 / night

£1,610 / week

Holiday villa with shared pool in Rum Point

Rum Point villa

3 bedrooms / 3 bathrooms / sleeps 8

1

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from £264 / night

£3,020 / week

Holiday apartment in Cayman Islands

Bodden Town apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 22 minutes

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from £58 / night

£997 / week

Cayman Islands holiday apartment accommodation

Bodden Town apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 22 minutes

Match: Water sports

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from £58 / night

£997 / week

Holiday home with shared pool in Cayman Islands

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

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from £230 / night

£1,610 / week

Holiday condo rental

West Bay condo

4 bedrooms / 5 bathrooms / sleeps 10

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from £771 / night

£5,394 - £14,639 / week

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!

19

Responds fast! avg. 3 hours 49 minutes

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from £221 / night

£1,541 / week

Holiday home rental

Gun Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

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from £462 / night

£3,230 / week

Cayman Islands holiday apartment rental

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

9

Responds fast! avg. 1 hour 0 minutes

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from £264 / night

£1,847 / week

Cayman Islands holiday home rental

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 12

1

Responds fast! avg. 3 hours 48 minutes

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from £735 / night

£5,141 / week

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!

26

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from £134 / night

£932 / week

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

Responds fast! avg. 3 hours 10 minutes

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from £199 / night

£1,390 - £2,065 / week

Cayman Brac holiday villa rental

Cayman Brac villa

3 bedrooms / 5 bathrooms / sleeps 8

7

Responds fast! avg. 29 minutes

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from £308 / night

£2,440 - £3,057 / week

Holiday condo with shared pool in Seven Mile Beach

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

5

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from £181 / night

£1,266 / week

Holiday villa accommodation

Cayman Brac villa

2 bedrooms / 2 bathrooms / sleeps 4

1

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from £161 / night

£1,070 - £1,258 / week

Cayman Islands holiday home rental

Cayman Brac house

2 bedrooms / 1 bathroom / sleeps 4

3

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from £135 / night

£941 / week

Holiday home in Old Man Bay

Old Man Bay house

4 bedrooms / 4 bathrooms / sleeps 10

“Fantastic” This villa is in a beautiful spot on the island, very quiet on the north shore. The house is laid out perfectly for a vacationing family. We had the best snorkeling ever right off the back of the house, saw octopus, lobster, eel and lots of fish. The service was great and we no problems with anything in the house! Perfect vacation,

26

Responds fast! avg. 3 hours 56 minutes

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from £516 / night

£3,608 / week

Holiday home in North Side

North Side house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 49 minutes

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from £287 / night

£2,007 / week

Holiday home in Rum Point

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 3 hours 56 minutes

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from £369 / night

£2,578 / week

Home rental in Cayman Islands

Rum Point house

4 bedrooms / 3 bathrooms / sleeps 8

“Beautiful accommodations!” Tara sand is simply a gorgeous property and well outfitted for our group of eight. The kitchen is roomy allowing everybody to take part with family meals and the dinning area is large enough to have a few friends over for dinner. The beach can't be matched. Some kayaks on the property would have been great. Be sure to take snorkeling gear as there is much to see right off shore! It was great to have washer and dryer, dishwasher, microwave and a water cooler. Unfortunately, the oven wasn't working. Important to get groceries in town before heading to Cayman Kai as there is not any place really close by. If getting away to a peaceful paradise is what you are looking for, this is the place.

5

Responds fast! avg. 3 hours 49 minutes

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from £922 / night

£6,454 / week

Holiday home with swimming pool 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

Responds fast! avg. 3 hours 49 minutes

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from £879 / night

£6,151 / week

Holiday apartment with shared pool in Cayman Islands

West Bay apartment

1 bedroom / 1 bathroom / sleeps 4

15

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from £165 / night

£1,150 / week

Holiday villa with shared pool in Cayman Islands

East End villa

3 bedrooms / 4 bathrooms / sleeps 8

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from £246 / night

£1,717 / week

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

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from £255 / night

£1,672 - £2,675 / week

Holiday guest house in Spot Bay

Spot Bay guest house

2 bedrooms / 1 bathroom / sleeps 4

1

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from £107 / night

£642 / week

Holiday guest house with swimming pool in Cayman Islands

George Town guest house

5 bedrooms / 5 bathrooms / sleeps 10

2

Responds fast! avg. 3 hours 17 minutes

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from £1,059 / night

£7,411 / week

Holiday home with shared pool in Cayman Islands

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 6

“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)

27

Responds fast! avg. 2 hours 2 minutes

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from £243 / night

£1,699 - £3,397 / week

Holiday home with swimming pool in Cayman Islands

Rum Point house

5 bedrooms / 3 bathrooms / sleeps 12

“Excellent Vacation for Familes” Great house awesome location. Loved being on the quite side of the island and walking on the beach to Starfish Point. Great place for families with young kids. Cannot wait to go back!

5

Responds fast! avg. 3 hours 49 minutes

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from £611 / night

£4,275 / week

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

Responds fast! avg. 3 hours 49 minutes

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from £510 / night

£3,570 / week

Home rental in Cayman Islands with shared pool

North Side house

2 bedrooms / 3 bathrooms / sleeps 6

3

Responds fast! avg. 1 hour 18 minutes

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from £222 / night

£1,554 / week

Home rental in Cayman Islands with swimming pool

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

Responds fast! avg. 3 hours 49 minutes

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from £510 / night

£3,570 / week

Holiday apartment with shared pool in Seven Mile Beach

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 7

5

Responds fast! avg. 2 hours 18 minutes

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from £176 / night

£1,229 / week

Cayman Islands holiday home rental

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 10

“Over the top trip!” We had an amazing, peaceful, relaxing, fun, beautiful stay at Coral Kai. It met our expectations and beyond! We loved the house, pool, and beach area. We want to go back!

6

Responds fast! avg. 3 hours 49 minutes

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from £801 / night

£5,608 / week

Holiday cottage in Cayman Islands

West Bay cottage

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 10 minutes

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from £246 / night

£1,672 / week

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.

6

Responds fast! avg. 3 hours 49 minutes

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from £675 / night

£4,725 / week

Holiday apartment in Cayman Islands

West Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

15

Responds fast! avg. 49 minutes

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from £265 / night

£1,544 - £2,647 / week

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rentals in Cayman Islands

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