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Cayman Islands

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60 Holiday homes

Filters applied: Water sports (60)

Travellers going to Cayman Islands are booking January dates now. Secure your holiday home today and have the perfect trip.

7

Holiday condo in Cayman Islands

Grand Cayman / Rum Point

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
This newly refurbished 2 Bed/2 Bath condo is literally located steps away from world famous Rum Point Beach at the quaint condo development of The Island Houses.  …see more

from £219 / night

£1528 - £2773 / week

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from £219 / night

(6) Very Good 

21

Holiday guest house in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Your own private Seven Mile Beach area 2 bed / 2 bath 'home away from home', with the best snorkeling on all of SMB within 2 blocks of your door step! From us$100/ night..."Cayman's Best Value!" Close to everything yet away from the crowds!  …see more

from £127 / night

£870 - £1552 / week

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from £127 / night

(1) Excellent 

13

Holiday villa with shared pool in Rum Point

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting  …see more

from £158 / night

£1106 - £5278 / week

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from £158 / night

(4) Excellent 

29

Holiday condo with shared pool in Cayman Islands

Grand Cayman / Seven Mile Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Our beach-front vacation home offers guests a luxury standard of vacation accommodation, with incredible views across the bay and over the pristine sands of Seven Mile Beach. Large luxury condos like those at Sea Breeze are hard to find on Grand Cayman, sleeping up to  …see more

from £667 / night

£8096 - £12024 / week

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from £667 / night

23

Grand Cayman / Seven Mile Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £235 / night

£1639 / week

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from £235 / night

(2) Excellent 

24

Grand Cayman / North Side

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

 …see more

from £187 / night

£1310 - £1588 / week

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from £187 / night

6

Grand Cayman / Bodden Town

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £358 / night

£2381 / week

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from £358 / night

(20) Excellent 

65

Cayman Islands / Grand Cayman

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £254 / night

£1667 - £2889 / week

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from £254 / night

18

Grand Cayman / North Side

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £175 / night

£1223 - £1500 / week

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from £175 / night

11

Cayman Brac / West End

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

 …see more

from £122 / night

£814 / week

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from £122 / night

(6) Excellent 

17

Grand Cayman / West Bay

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £159 / night

£1112 - £2084 / week

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from £159 / night

15

Grand Cayman / North Side

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £155 / night

£1084 - £1639 / week

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from £155 / night

(7) Excellent 

30

Grand Cayman / Seven Mile Beach

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £108 / night

£750 - £2556 / week

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from £108 / night

9

Grand Cayman / Seven Mile Beach

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

 …see more

from £635 / night

£4445 - £6548 / week

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from £635 / night

10

George Town holiday guest house rental

Grand Cayman / George Town

4 14 1 night min

  • 4 bedrooms
  • Sleeps 14
  • 1 night min
  • Nearest beach 8 km
  • Child friendly
  • Air conditioning
Private rooms with private bathrooms, A/C and fan, hot/cold water, very comfortable. Languages: English, French, Italian and Portuguese. Enjoy the experience of living with a real Cuban family, and feel like home. Enjoy our meals, home made specially for you.Roof terrac  …see more

from £25 / night

£140 / week

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from £25 / night

6

Grand Cayman / East End

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £362 / night

£2532 / week

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from £362 / night

13

Grand Cayman / East End

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £362 / night

£2532 / week

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from £362 / night

(6) Excellent 

23

Grand Cayman / East End

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £199 / night

£1389 - £2223 / week

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from £199 / night

31

Rum Point holiday home rental

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting  …see more

from £160 / night

£1115 / week

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from £160 / night

(10) Very Good 

14

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £139 / night

£973 / week

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from £139 / night

(3) Excellent 

22

Grand Cayman / East End

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from £199 / night

£1389 - £2223 / week

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from £199 / night

24

Grand Cayman / George Town

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £2835 / night

£19842 - £39683 / week

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from £2835 / night

15

Grand Cayman / Bodden Town

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £120 / night

£715 / week

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from £120 / night

(1) Excellent 

21

Cayman Islands / Cayman Brac

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £135 / night

£913 - £1208 / week

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from £135 / night

(1) Very Good 

14

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £158 / night

£1106 / week

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from £158 / night

9

Grand Cayman / Old Man Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £143 / night

£1000 - £1112 / week

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from £143 / night

(5) Excellent 

17

Grand Cayman / Seven Mile Beach

6 17 Min stay varies

  • 6 bedrooms
  • Sleeps 17
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £1417 / night

£9921 - £27778 / week

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from £1417 / night

20

Grand Cayman / Rum Point

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £239 / night

£1667 - £2362 / week

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from £239 / night

(3) Excellent 

23

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

 …see more

from £199 / night

£1250 - £3250 / week

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from £199 / night

(6) Very Good 

31

Grand Cayman / Seven Mile Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £254 / night

£1773 / week

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from £254 / night

32

Grand Cayman / Seven Mile Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £596 / night

£3770 - £7937 / week

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from £596 / night

(3) Excellent 

21

Grand Cayman / Seven Mile Beach

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £158 / night

£1106 / week

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from £158 / night

(2) Excellent 

24

Grand Cayman / North Side

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £158 / night

£1107 - £2084 / week

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from £158 / night

(1) Excellent 

18

Grand Cayman / West Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

 …see more

from £108 / night

£751 / week

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from £108 / night

(5) Excellent 

18

Grand Cayman / West Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

 …see more

from £358 / night

£2500 / week

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from £358 / night

(7) Excellent 

28

Grand Cayman / Seven Mile Beach

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

 …see more

from £500 / night

£3334 - £6786 / week

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from £500 / night

46

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

 …see more

from £239 / night

£2084 / week

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from £239 / night

29

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

 …see more

from £239 / night

£1806 / week

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from £239 / night

(1) Excellent 

27

Grand Cayman / Seven Mile Beach

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £262 / night

£1786 - £3671 / week

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from £262 / night

9

Grand Cayman / Seven Mile Beach

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly

 …see more

from £179 / night

£1250 / week

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from £179 / night

Top Destination reviews

Villa Emmanuel
Wonderful experience!

Villa Emmanuel was perfect for us!! We stayed for two weeks and everyone loved it! The house, pool and oven were amazing. Villa Emmanuel is away from the busy area of Grand Cayman, but we could walk to either Kaibo or Rum Point for a restaurant or … see more

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