Air conditioned apartments and villas to rent in Cayman Islands

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Cayman Islands

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196 Holiday homes

Filters applied: Air conditioning (196)

Travellers going to Cayman Islands are booking February 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 £226 / night

£1578 - £1951 / week

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from £226 / 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 £164 / night

£1142 - £5451 / week

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from £164 / 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 £705 / night

£8361 - £12705 / week

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from £705 / night

14

Holiday home in Cayman Islands

Cayman Islands / Cayman Brac

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Air conditioning
  • Private garden
Welcome to The Breeze. Located directly on the beach in beautiful Cayman Brac, just 25 mins from Grand Cayman by air. Recently renovated, we have 2 lovely bedrooms with ensuites. Full sitting room, dining room and kitchen with full amenities. Enclosed porch with day be  …see more

from £123 / night

£779 - £894 / week

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from £123 / 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.<br />  …see more

from £25 / night

£140 / week

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from £25 / 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 foo  …see more

from £394 / night

£2755 / week

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from £394 / night

(7) Excellent 

11

Grand Cayman / Bodden Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £103 / night

£656 - £2460 / week

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from £103 / night

19

Grand Cayman / North Side

3 8 Min stay varies

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

 …see more

from £267 / night

£1865 - £5738 / week

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from £267 / 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 £615 / night

£4304 / week

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from £615 / night

(1) Excellent 

34

Cayman Islands

2 6 Min stay varies

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

 …see more

from £214 / night

£1492 - £3323 / week

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from £214 / night

(2) Excellent 

38

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 £103 / night

£718 - £1128 / week

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from £103 / 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 £144 / night

£902 - £1476 / week

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from £144 / night

23

Grand Cayman / East End

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning

 …see more

from £117 / night

£816 - £980 / week

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from £117 / 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 £140 / night

£943 - £1247 / week

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from £140 / night

34

Cayman Islands

3 6 Min stay varies

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

 …see more

from £450 / night

£3150 - £9100 / week

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from £450 / night

(5) Excellent 

21

Grand Cayman / Seven Mile Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.11 km
  • Child friendly

 …see more

from £146 / night

£914 - £1773 / week

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from £146 / night

(1) Excellent 

17

Grand Cayman / George Town

2 6 Min stay varies

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

 …see more

from £246 / night

£1722 - £3587 / week

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from £246 / night

(11) Excellent 

14

Cayman Islands / Little Cayman

4 10 Min stay varies

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

 …see more

from £296 / night

£2066 - £5853 / week

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from £296 / night

14

Cayman Brac / West End

3 8 Min stay varies

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

 …see more

from £164 / night

£1148 - £1492 / week

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from £164 / 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 £126 / night

£841 / week

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from £126 / night

33

Cayman Islands

2 6 Min stay varies

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

 …see more

from £230 / night

£1607 - £3587 / week

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from £230 / night

(1) Excellent 

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 £369 / night

£2460 / week

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from £369 / 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 £111 / night

£775 - £2640 / week

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from £111 / night

(7) Excellent 

17

Grand Cayman / West Bay

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £164 / night

£1148 - £1636 / week

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from £164 / 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 £146 / night

£1014 - £2124 / week

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from £146 / night

15

Grand Cayman / Seven Mile Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

 …see more

from £615 / night

£4099 - £10246 / week

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from £615 / 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 £287 / night

£2003 / week

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from £287 / night

(5) Excellent 

16

Cayman Islands / Little Cayman

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from £222 / night

£1550 - £3558 / week

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from £222 / night

(18) Excellent 

15

Cayman Islands / Grand Cayman

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £144 / night

£1005 - £2382 / week

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from £144 / night

(1) Very Good 

15

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.11 km
  • Child friendly

 …see more

from £128 / night

£800 - £1355 / week

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from £128 / 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 £123 / night

£734 / week

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from £123 / night

(1) Excellent 

23

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 £328 / night

£2296 - £5164 / week

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from £328 / night

(1) Excellent 

23

Cayman Islands / Grand Cayman

6 15 Min stay varies

  • 6 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £279 / night

£1951 - £8607 / week

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from £279 / 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 £242 / night

£1693 / week

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from £242 / night

(8) Excellent 

12

Grand Cayman / Seven Mile Beach

1 4 Min stay varies

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

 …see more

from £144 / night

£1005 - £2869 / week

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from £144 / 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 £152 / night

£1062 - £1894 / week

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from £152 / 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 £123 / night

£861 - £2439 / week

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from £123 / night

(3) Excellent 

23

Cayman Islands / Little Cayman

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £328 / night

£2290 / week

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from £328 / 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 £148 / night

£1033 - £1148 / week

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from £148 / night

31

Cayman Islands

2 6 Min stay varies

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

 …see more

from £254 / night

£1773 - £3833 / week

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from £254 / night