Villas with a pool Cayman Islands | Apartments to rent with swimming facilities | Holiday Lettings

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Cayman Islands

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114 Holiday homes

Filters applied: Swimming pool (114)

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

(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 £160 / night

£1115 - £5320 / week

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from £160 / 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 £672 / night

£8160 - £12120 / week

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from £672 / night

20

Grand Cayman / George Town

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £600 / night

£4200 / week

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from £600 / 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 £360 / night

£2400 / week

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from £360 / night

(2) Excellent 

25

Grand Cayman / East End

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £135 / night

£940 - £1260 / week

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from £135 / night

31

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £140 / night

£880 - £1960 / week

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from £140 / night

(12) Excellent 

22

Cayman Islands / Grand Cayman

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £140 / night

£980 - £2072 / week

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from £140 / 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 £188 / night

£1320 - £1600 / week

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from £188 / 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 £256 / night

£1680 - £2912 / week

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from £256 / 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 £140 / night

£980 / week

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from £140 / night

(3) Very Good 

23

Cayman Islands / Grand Cayman

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £144 / night

£1008 - £2968 / week

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from £144 / 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

£756 - £2576 / week

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from £108 / night

18

Grand Cayman / East End

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £168 / night

£1072 - £1484 / week

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from £168 / night

(2) Very Good 

26

Grand Cayman / West Bay

2 6 1 night min

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

 …see more

from £148 / night

£1036 - £1988 / week

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from £148 / night

(4) Excellent 

12

Grand Cayman / Rum Point

2 4 3 nights min

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

 …see more

from £200 / night

£1200 / week

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from £200 / night

(2) Excellent 

27

Little Cayman / South Town

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

 …see more

from £120 / night

£716 / week

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from £120 / night

(3) Excellent 

26

Cayman Islands / Grand Cayman

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £456 / night

£3192 - £9044 / week

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from £456 / night

(22) Excellent 

12

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £152 / night

£1064 - £3136 / week

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from £152 / night

(3) Excellent 

18

Cayman Islands / Grand Cayman

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £240 / night

£1680 - £3500 / week

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from £240 / night

(13) Very Good 

17

Cayman Islands / Grand Cayman

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £120 / night

£840 - £2380 / week

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from £120 / night

70

Cayman Islands / Grand Cayman

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £308 / night

£2156 / week

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from £308 / night

(9) Very Good 

23

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £200 / night

£1400 - £3500 / week

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from £200 / night

5

Holiday villa with shared pool, golf nearby in East End

Grand Cayman / East End

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Premier Morritt's Tortuga Club resort offers a luxury beach front paradise atmosphere, with 2 pools a waterfall and swim up cocktail bar. Each air conditioned apartment has a balcony and a fully equipped kitchen. The property's restaurant serves gourmet food and ther  …see more

from £384 / night

£2688 / week

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from £384 / night

(13) Very Good 

15

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £144 / night

£1008 - £3220 / week

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from £144 / night

(2) Excellent 

12

Grand Cayman / Seven Mile Beach

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £180 / night

£1160 - £2236 / week

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from £180 / 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 £160 / night

£1120 - £2100 / week

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from £160 / night

(5) Excellent 

18

Cayman Islands / Grand Cayman

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £208 / night

£1456 - £4116 / week

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from £208 / night

(18) Excellent 

27

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £152 / night

£1064 - £1540 / week

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from £152 / night

(2) Excellent 

29

Grand Cayman / Seven Mile Beach

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool

 …see more

from £142 / night

£989 - £2073 / week

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from £142 / 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 £144 / night

£1008 - £1120 / week

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from £144 / night

21

Grand Cayman / West Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £152 / night

£1064 - £3612 / week

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from £152 / 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 £640 / night

£4480 - £6600 / week

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from £640 / night

(1) Excellent 

17

Cayman Islands / Grand Cayman

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £128 / night

£896 - £1960 / week

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from £128 / night

9

Grand Cayman / Seven Mile Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £420 / night

£2940 / week

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from £420 / 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

£720 / week

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from £120 / night

(14) Excellent 

24

Cayman Islands / Grand Cayman

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £316 / night

£2212 - £4676 / week

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from £316 / night

(4) Very Good 

27

Grand Cayman / Seven Mile Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £108 / night

£756 - £1792 / week

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from £108 / 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 £160 / night

£1115 / week

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from £160 / night

(9) Excellent 

11

Cayman Islands / Grand Cayman

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £136 / night

£952 - £2044 / week

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from £136 / 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 £2858 / night

£20000 - £40000 / week

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from £2858 / 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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