50 Best Cayman Islands Vacation rentals on Holiday Lettings - Condos

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Vacation rentals Grand Cayman
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219 Vacation rentals

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7

Vacation 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. There are 17 units in The Island Houses that wrap around the northern end of the Rum Point Lagoon. The neigh  …see more

from $275 / night

$1925 - $3493 / week

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from $275 / night

(6) Very Good 

21

Vacation 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 mi
  • 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 $160 / night

$1095 - $1955 / week

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from $160 / night

(1) Excellent 

13

Vacation 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 $199 / night

$1393 - $6650 / week

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from $199 / 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 $295 / night

$2065 / week

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from $295 / night

(4) Excellent 

29

Vacation 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 mi
  • 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 $840 / night

$10200 - $15150 / week

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from $840 / night

17

Grand Cayman / East End

1 2 7 nights min

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

 …see more

from $143 / night

$995 - $1195 / week

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from $143 / 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 $125 / night

$800 - $2700 / week

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from $125 / 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 $750 / night

$5250 / week

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from $750 / night

(4) 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 mi
  • Child friendly

 …see more

from $200 / night

$1260 - $4865 / week

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from $200 / 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 $450 / night

$3000 / week

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from $450 / 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 $168 / night

$1175 - $1575 / week

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from $168 / night

31

Cayman Islands / Grand Cayman

2 6 Min stay varies

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

 …see more

from $175 / night

$1100 - $2450 / week

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from $175 / 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 $270 / night

$1890 - $4340 / week

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from $270 / night

(18) Excellent 

15

Cayman Islands / Grand Cayman

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $175 / night

$1225 - $2905 / week

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from $175 / night

13

Cayman Islands / Grand Cayman

1 4 Min stay varies

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

 …see more

from $150 / night

$1000 - $2100 / week

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from $150 / 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 $220 / night

$1540 - $1890 / week

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from $220 / 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 $175 / night

$1225 - $2590 / week

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from $175 / 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 mi
  • Swimming pool

 …see more

from $235 / night

$1650 - $2000 / week

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from $235 / 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 about children

 …see more

from $320 / night

$2100 - $3640 / week

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from $320 / 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 about children

 …see more

from $175 / night

$1225 / week

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from $175 / 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 $180 / night

$1260 - $3710 / week

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from $180 / 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 mi
  • Swimming pool

 …see more

from $135 / night

$945 - $3220 / week

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from $135 / 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 $210 / night

$1339 - $1854 / week

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from $210 / night

14

Vacation 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 $150 / night

$950 - $1090 / week

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from $150 / night

(13) Very Good 

13

Cayman Islands / Grand Cayman

1 4 Min stay varies

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

 …see more

from $145 / night

$1015 - $2240 / week

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from $145 / 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 $195 / night

$1365 - $2065 / week

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from $195 / 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 $185 / night

$1295 - $2485 / week

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from $185 / 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 $250 / night

$1500 / week

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from $250 / 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 mi
  • Swimming pool

 …see more

from $150 / night

$895 / week

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from $150 / 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 $570 / night

$3990 - $11305 / week

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from $570 / night

10

George Town Vacation guest house rental

Grand Cayman / George Town

4 14 1 night min

  • 4 bedrooms
  • Sleeps 14
  • 1 night min
  • Nearest beach 8 mi
  • Child friendly
  • Air conditioning
Right at the Historical center of Santiago de Cuba, Casa "Don Carlos" offers the best host in the city, we speak fluent English and some French, Italian and Portuguese. Feel the warmt of a Cuban family, and enjoy the city of Santiago as never before, at a walk  …see more

from $32 / night

$175 / week

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from $32 / 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 $190 / night

$1330 - $3920 / week

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from $190 / night

(1) Excellent 

25

Grand Cayman / West Bay

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Air conditioning

 …see more

from $275 / night

$1925 / week

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from $275 / 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 $300 / night

$2100 - $4375 / week

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from $300 / 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 $150 / night

$1050 - $2975 / week

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from $150 / night

18

Grand Cayman / East End

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $250 / night

$1648 - $2575 / week

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from $250 / 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 $452 / night

$3164 / week

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from $452 / night

33

Rum Point Vacation 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 $259 / night

$1813 / week

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from $259 / 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 $385 / night

$2695 / week

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from $385 / 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 $452 / night

$3164 / week

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from $452 / night

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