50 Best Grand Cayman Vacation rentals on Holiday Lettings - Villas

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Condos Seven Mile Beach
28 properties
West Bay
23 properties
East End
21 properties
Rum Point
15 properties
George Town
9 properties
Bodden Town
9 properties
Apartments North Side
8 properties

Grand Cayman

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184 Vacation rentals

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(4) Excellent 

29

Vacation condo with shared pool in Seven Mile Beach

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 $860 / night

$10200 - $15500 / week

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from $860 / night

37

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 $220 / night

$1534 / week

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from $220 / night

31

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 $200 / night

$1394 / week

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from $200 / night

30

Home rental in Rum Point

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 $200 / night

$1394 / week

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from $200 / 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 $220 / night

$1533 - $6293 / week

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from $220 / night

16

Vacation villa in East End

Grand Cayman / East End

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our rental villas are situated in the quaint community of East End on Grand Cayman, away from all the noise and congestion of Georgetown and 7-mile beach. Parking is a HUGE problem in Georgetown and on 7 mile beach -- there are very few public parking lots, and  …see more

from $215 / night

$1353 - $3908 / week

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from $215 / night

7

Vacation condo in Rum Point

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 - $2976 / week

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from $275 / night

7

Cottage rental in East End

Grand Cayman / East End

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Both beds are QUEEN sized. The Cottage provides basic accommodation, nothing fancy, no marble foyer nor granite countertops, but it does give you spotlessly clean accommodation literally steps from a powdery - white sand beach. We also have a large HOT TUB. O  …see more

from $136 / night

$999 - $1575 / week

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from $136 / night

30

Vacation home in Rum Point

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 $200 / night

$1394 / week

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from $200 / night

9

East End Vacation apartment rental

Grand Cayman / East End

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This spacious, private 1 bedroom apartment takes up the entire ground floor level of a large 3-storey house in the East End of Grand Cayman. It walks out directly to a stunningly beautiful white, sandy beach, lush with vegetation and palm trees, right on your doorstep.  …see more

from $151 / night

$1001 - $2901 / week

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from $151 / 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 $31 / night

$174 / week

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from $31 / 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 $299 / night

$2093 / week

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from $299 / night

24

Vacation apartment in Bodden Town

Grand Cayman / Bodden Town

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
If you're looking for a perfect holiday relaxing on white powdery sand, swimming in crystal warm Caribbean waters, enjoying fantastic food as Grand Cayman is known as the 'Culinary Capital of the Caribbean' then Gran Cayman island is the perfect island to  …see more

from $171 / night

$1021 - $1511 / week

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from $171 / night

5

East End Vacation studio rental

Grand Cayman / East End

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Blue Sea Hideaway is a 500 square foot studio apartment that offers you basic, reasonably priced accommodation with all the comforts of home. You have a full sized fridge, microwave convection oven, ceramic cooktop and a dishwasher. [SEE NOTE BELOW] There is a qu  …see more

from $125 / night

$851 - $2000 / week

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from $125 / 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 $350 / night

$2443 / week

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from $350 / night

5

Vacation 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 $481 / night

$3361 / week

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from $481 / night

16

East End Vacation home rental

Grand Cayman / East End

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Designer decorated spacious Beach House on a gorgeous, private, white powder sand beach. Two master bedrooms with terraces overlooking the ocean, one with a King Bed, the other with a Queen and both with ensuite bathrooms. 3rd bedroom has twin beds and there is a d  …see more

from $350 / night

$2376 - $6050 / week

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from $350 / night

29

Bodden Town Vacation apartment accommodation

Grand Cayman / Bodden Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
The 'Sunset paradise 1' apartment is a large two bedroom, two bathroom ground floor apartment with nice sea view terrace located in the historic Bodden Town and just across the road from the beach. It's a perfect location in the middle of Grand Cayman isl  …see more

from $171 / night

$1021 - $1351 / week

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from $171 / night

(11) 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 - $3001 / week

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from $125 / 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 mi
  • Swimming pool

 …see more

from $200 / night

$1400 - $1856 / week

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from $200 / night

(1) Excellent 

5

Grand Cayman / West Bay

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $226 / night

$1650 - $2801 / week

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from $226 / night

(4) Very Good 

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 $168 / night

$1176 - $1376 / week

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from $168 / night

(6) 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 $251 / night

$1500 / week

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from $251 / 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 $136 / night

$946 - $3220 / week

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from $136 / night

(22) Excellent 

34

Grand Cayman / North Side

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

 …see more

from $501 / night

$3151 - $4250 / week

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from $501 / night

21

Grand Cayman / West Bay

Studio 6 Min stay varies

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

 …see more

from $191 / night

$1331 - $4515 / week

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from $191 / 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 $143 / night

$995 - $1196 / week

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from $143 / 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 $151 / night

$900 / week

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from $151 / night

(5) Excellent 

40

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 $1920 / night

$13440 / week

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from $1920 / night

38

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 $386 / night

$2695 / week

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from $386 / night

(3) Excellent 

22

Grand Cayman / East End

3 6 Min stay varies

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

 …see more

from $226 / night

$2100 - $2801 / week

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from $226 / 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 mi
  • Swimming pool

 …see more

from $178 / night

$1236 - $2591 / week

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from $178 / night

(20) Excellent 

27

Cayman Islands / Grand Cayman

2 6 5 nights min

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

 …see more

from $175 / night

$1575 / week

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from $175 / night

8

Grand Cayman / West Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

 …see more

from $200 / night

$1400 - $2801 / week

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from $200 / night

(1)  

14

Grand Cayman / West Bay

Studio 4 Min stay varies

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

 …see more

from $226 / night

$1575 - $4270 / week

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from $226 / night

20

Grand Cayman / West Bay

Studio 4 Min stay varies

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

 …see more

from $155 / night

$1085 - $2520 / week

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from $155 / night

(8) Excellent 

23

Grand Cayman / East End

3 6 Min stay varies

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

 …see more

from $226 / night

$2100 - $2801 / week

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from $226 / 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 $166 / night

$1156 - $2066 / week

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from $166 / night

(2) Very Good 

21

Grand Cayman / West Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning

 …see more

from $145 / night

$1116 / week

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from $145 / night

(1) Excellent 

17

Grand Cayman / George Town

Studio 6 Min stay varies

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

 …see more

from $300 / night

$2100 - $4376 / week

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from $300 / night