Grand Cayman Vacation Rental Getaways

Select a vacation destination from the list below.
You can narrow your search by selecting specific travel dates, a price range or other search options.

Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Halcyon Days

Grand Cayman
A private pool, sunny décor, your own private boat dock, and a tucked-away location at the end of a ...
Villa 2 / 2 / 5

*
Online booking available

$295 - $735
Per Night

$2065 - $5145
Per Week

Kaibo Yacht Club #29C

Cayman Kai
One of the most popular destinations on Grand Cayman, Kaibo Yacht Club is a haven for boaters, Cayma...
Condo 2 / 2 / 4

*
Online booking available

$155 - $440
Per Night

$1085 - $3080
Per Week

Moon Bay #31

Grand Cayman
Moon Bay #31 is a wonderful complex located on the majestic south shore. Just a few (barefoot) steps...
Condo 2 / 1 / 6

*
Online booking available

$130 - $360
Per Night

$910 - $2520
Per Week

The Grandview 411

Grand Cayman
Ground floor unit with great outdoor patio furniture and an easy walk out to our beach, pool and gar...
Condo 2 / 2 / 6

*
Online booking available

$410 - $645
Per Night

$2870 - $4515
Per Week

The Grandview 1221

Grand Cayman
Second floor unit with an amazing interior with over-sized floor tiles, granite counter tops in the ...
Condo 2 / 2 / 6

*
Online booking available

$500 - $735
Per Night

$3500 - $5145
Per Week

Coral Reef - Cayman

West Bay
This spacious and deluxe private beach front villa could be considered as one of the most sought aft...
Villa 5 / 4 / 12

*
Online booking available

$3250 - $6420
Per Night

$22750 - $44940
Per Week

Villa Emmanuel

Cayman Kai
Gather your favorite people and head to 5-bedroom, 4-bath Villa Emmanuel, on the quiet shores of Cay...
Villa 5 / 4 / 10

*
Online booking available

$600 - $1575
Per Night

$4200 - $11025
Per Week

George Town Villas 301

Seven Mile Beach
Third-floor views of the glittering Caribbean, 2 Master suites with attached, modern baths, outdoor ...
Condo 2 / 2 / 5

*
Online booking available

$190 - $525
Per Night

$1330 - $3675
Per Week

Villas Pappagallo #7

West Bay
On the hunt for away-from-it-all accommodations on Grand Cayman, where you can have a Caribbean beac...
Condo 1 / 1 / 4

*
Online booking available

$155 - $360
Per Night

$1085 - $2520
Per Week

The Grandview 311

Grand Cayman
The beach is just steps away from the private screened patio of this ground floor unit. Plantation s...
Condo 2 / 2 / 6

*
Online booking available

$410 - $645
Per Night

$2870 - $4515
Per Week

Discovery Point Club #18

Seven Mile Beach
Come and see why Discovery Point Club, on coveted Seven Mile Beach, boasts 300 five-star reviews and...
Condo 2 / 2 / 6

*
Online booking available

$190 - $645
Per Night

$1330 - $4515
Per Week

On The Rocks

Grand Cayman
Proudly resting on the Beach Bay bluff over the shimmering azure Caribbean waters. This beautiful “O...
Villa 7 / 4 / 14

*
Online booking available

$570 - $1615
Per Night

$3990 - $11305
Per Week

Treasure Cove

Cayman Kai
A fantastic place for reunions with friends or family at this secluded, crown-jewel property situate...
Villa 6 / 4 / 15

*
Online booking available

$750 - $2200
Per Night

$5250 - $15400
Per Week

On The Bay #104

Old Man Bay
Tucked into lush tropical landscaping on the ground floor of an intimate beachfront resort, 2-bedroo...
Condo 2 / 2 / 6

*
Online booking available

$130 - $320
Per Night

$910 - $2240
Per Week

Kailypso

Rum Point
Kailypso is a spacious and comfortable home situated on a wide white sandy beach inside a little cov...
Home 3 / 2 / 8

*
Online booking available

$495 - $1045
Per Night

$3465 - $7315
Per Week

No Snow

Drift Wood Village
No Snow- is located on the Northside of the island just about 1/2 Mile east of the Rum Point Club. T...
Villa 6 / 4 / 12

*
Online booking available

$990 - $1460
Per Night

$6930 - $10220
Per Week

The Grandview 1021

Grand Cayman
Perched on the edge of stunning Seven Mile Beach, this second floor unit offers front row seats to t...
Condo 2 / 2 / 6

*
Online booking available

$500 - $735
Per Night

$3500 - $5145
Per Week

 

More Getaway Locations and Properties