50 Best Grand Cayman Vacation rentals on Holiday Lettings - Villas

Close

View larger map

Also consider

Condos Seven Mile Beach
36 properties
West Bay
21 properties
Rum Point
13 properties
East End
12 properties
George Town
6 properties
Bodden Town
6 properties
Apartments North Side
5 properties

Grand Cayman

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

174 Vacation rentals

Travelers going to Grand Cayman are booking December dates now. Secure your vacation rental today and have the perfect trip.

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 $273 / night

$1910 - $3466 / week

Book View

from $273 / 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 $198 / night

$1383 - $6598 / week

Book View

from $198 / 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 $159 / night

$1087 - $1940 / week

Book View

from $159 / 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

$794 - $2679 / week

Book View

from $125 / night

(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 $834 / night

$10120 - $15031 / week

Book View

from $834 / 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 $293 / night

$2049 / week

Book View

from $293 / 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 $745 / night

$5209 / week

Book View

from $745 / 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 $134 / night

$938 - $3195 / week

Book View

from $134 / 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 $167 / night

$1166 - $1563 / week

Book View

from $167 / 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 $234 / night

$1638 - $1985 / week

Book View

from $234 / 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 $318 / night

$2084 - $3612 / week

Book View

from $318 / 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 $176 / night

$1225 - $2591 / week

Inquire View

from $176 / night

13

Cayman Islands / Grand Cayman

1 4 Min stay varies

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

 …see more

from $149 / night

$993 - $2084 / week

Book View

from $149 / 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 about children

 …see more

from $199 / night

$1389 - $2605 / week

Book View

from $199 / 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 $249 / night

$1489 / week

Book View

from $249 / 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 $174 / night

$1216 / week

Book View

from $174 / 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 $142 / night

$988 - $1186 / week

Book View

from $142 / 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 $174 / night

$1092 - $2431 / week

Book View

from $174 / night

(2) Excellent 

14

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

$1016 - $2241 / week

Inquire View

from $145 / 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 $151 / night

$1050 - $2975 / week

Inquire View

from $151 / 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 $224 / night

$1439 - $2773 / week

Book View

from $224 / night

(4) Very Good 

25

Grand Cayman / West Bay

2 6 5 nights min

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

 …see more

from $224 / night

$1563 - $1910 / week

Book View

from $224 / 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

$2101 - $4375 / week

Inquire View

from $300 / 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 $149 / night

$893 / week

Book View

from $149 / 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

$177 / week

Book View

from $32 / 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 $571 / night

$3991 - $11305 / week

Inquire View

from $571 / 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 $184 / night

$1285 - $2466 / week

Book View

from $184 / 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 $447 / night

$2977 / week

Book View

from $447 / 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 $449 / night

$3140 / week

Book View

from $449 / 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 $251 / night

$1751 - $4375 / week

Inquire View

from $251 / 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 mi
  • Swimming pool

 …see more

from $189 / night

$1320 - $1910 / week

Book View

from $189 / night

(17) Very Good 

13

Cayman Islands / Grand Cayman

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $191 / night

$1331 - $2241 / week

Inquire View

from $191 / 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 $198 / night

$1383 / week

Book View

from $198 / 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 $218 / night

$1521 / week

Book View

from $218 / night

(3) Excellent 

16

Cayman Islands / Grand Cayman

2 6 Min stay varies

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

 …see more

from $200 / night

$1400 - $3956 / week

Inquire View

from $200 / 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 $176 / night

$1225 - $2906 / week

Inquire View

from $176 / 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 $180 / night

$1260 - $4025 / week

Inquire View

from $180 / night

(4) Excellent 

21

Grand Cayman / Seven Mile Beach

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.11 mi
  • Child friendly

 …see more

from $199 / night

$1251 - $2396 / week

Book View

from $199 / 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 $449 / night

$3140 / week

Book View

from $449 / 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 $219 / night

$1528 - $1876 / week

Book View

from $219 / night