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

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111 Holiday homes

Filters applied: Swimming pool (111)

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

(1) Excellent 

13

Affordable Luxury 3 Bed/3 Bath Vacation Home (#5) - Rum Point villa sleeps 8

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 £154 / night

£1072 - £4577 / week

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from £154 / 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 £116 / night

£808 - £1154 / week

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from £116 / 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 £516 / night

£3608 / week

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from £516 / 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 £347 / night

£2308 / week

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from £347 / night

(4) Excellent 

29

Sea Breeze - A Luxury 4br + den SMB Condo - Seven Mile Beach condo sleeps 10

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
AUGUST & SEPTEMBER 2016 SPECIAL. STAY SIX NIGHTS AND GET SEVENTH FREE. DISCOUNT MANUALLY ADDED AFTER ENQUIRY. 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 Se  …see more

from £647 / night

£7693 - £11654 / week

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from £647 / night

18

Cayman Islands / Cayman Brac

2 6 3 nights min

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

 …see more

from £135 / night

£847 / 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 £135 / night

£847 - £1885 / week

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from £135 / night

(1) Excellent 

25

Grand Cayman / George Town

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £1539 / night

£10770 - £11847 / week

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from £1539 / night

(20) Excellent 

48

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 £212 / night

£1481 - £2800 / week

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from £212 / night

(7) Excellent 

50

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 £104 / night

£727 - £2477 / week

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from £104 / night

(11) Excellent 

13

Cayman Islands / Little Cayman

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £394 / night

£2753 - £7799 / week

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from £394 / night

(7) Very Good 

14

Grand Cayman / West Bay

2 6 3 nights min

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

 …see more

from £123 / night

£827 / week

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from £123 / 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 £147 / night

£1024 - £1481 / week

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from £147 / 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 £139 / night

£970 - £1077 / week

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from £139 / night

(9) Very Good 

23

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £283 / night

£1979 - £4947 / week

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from £283 / night

(10) Very Good 

14

Grand Cayman / Seven Mile Beach

2 6 3 nights min

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

 …see more

from £112 / night

£781 / week

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from £112 / 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 £181 / night

£1270 - £1539 / week

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from £181 / 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 £116 / night

£689 / week

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from £116 / night

17

Cayman Islands / Grand Cayman

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £547 / night

£3824 - £8220 / week

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from £547 / night

(17) Very Good 

22

Cayman Islands / Grand Cayman

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £357 / night

£2494 - £6926 / week

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from £357 / 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 £616 / night

£4308 - £6347 / week

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from £616 / 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 £143 / night

£997 - £1912 / week

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from £143 / 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 £174 / night

£1116 - £2150 / week

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from £174 / night

(9) Very Good 

24

Cayman Islands / Grand Cayman

7 26 Min stay varies

  • 7 bedrooms
  • Sleeps 26
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £2940 / night

£20580 - £40646 / week

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from £2940 / night

(14) Excellent 

24

Cayman Islands / Grand Cayman

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £431 / night

£3020 - £6384 / week

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from £431 / night

(11) Excellent 

13

Grand Cayman / Seven Mile Beach

2 4 5 nights min

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

 …see more

from £231 / night

£1616 / week

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from £231 / night

20

Cayman Islands / Grand Cayman

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £371 / night

£2600 - £9558 / week

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from £371 / night

5

Family Resort at Awesome Grand Cayman - East End villa sleeps 4

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 £370 / night

£2585 / week

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from £370 / night

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 £130 / night

£904 - £1212 / week

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from £130 / night

(22) Excellent 

12

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £215 / night

£1504 - £4433 / week

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from £215 / night

(12) Excellent 

22

Cayman Islands / Grand Cayman

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £191 / night

£1338 - £2829 / week

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from £191 / night

(12) Very Good 

17

Cayman Islands / Grand Cayman

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £170 / night

£1187 - £3364 / week

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from £170 / night

(12) Very Good 

17

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £164 / night

£1147 - £3174 / week

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from £164 / night

21

Grand Cayman / West Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £207 / night

£1453 - £4932 / week

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from £207 / night

(16) Very Good 

20

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 £345 / night

£2414 - £5501 / week

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from £345 / night

(13) Very Good 

15

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £204 / night

£1425 - £4551 / week

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from £204 / night

(2) Excellent 

23

Cayman Islands / Grand Cayman

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £197 / night

£1377 - £4053 / week

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from £197 / night

27

Cayman Islands / Grand Cayman

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £547 / night

£3824 - £8220 / week

Enquire View

from £547 / night

70

Cayman Islands / Grand Cayman

2 6 Min stay varies

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

 …see more

from £270 / night

£2074 / week

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from £270 / night

(2) Excellent 

24

Grand Cayman / Seven Mile Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £917 / night

£6423 - £16549 / week

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from £917 / 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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