Cayman Islands Vacation Rental Getaways

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  • Property Options
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  • 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

Villa La Playa

North Side
Villa La Playa is nestled in a tranquil inlet of water (not the open ocean). A pretty Cayman style w...
Condo 2 / 3 / 8

*
Online booking available

$540 - $1370
Per Night

$3780 - $9590
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

Kozy Kai - Sealodge #17

Cayman Kai
Romantics will love this 1-bedroom, 1-bath cottage right on the beach in Cayman Kai, less than a 5 m...
Condo 1 / 1 / 2

*
Online booking available

$190 - $320
Per Night

$1330 - $2240
Per Week

On The Bay #311

Old Man Bay
Escape to the quiet side of Grand Cayman. On The Bay, a small resort on the tranquil North Shore, pr...
Condo 3 / 3 / 6

*
Online booking available

$175 - $370
Per Night

$1225 - $2590
Per Week

Coral Reef

Seven Mile Beach
On prestigious Seven Mile Beach, there are very few private villas for rent. Most offerings are cond...
Villa 7 / 7.5 / 26

*
Online booking available

$2600 - $5135
Per Night

$18200 - $35945
Per Week

White Sands #3

Seven Mile Beach
Escape the hotel crowds and tuck into a quiet beachfront condo resort that has everything you need a...
Condo 1 / 1 / 2

*
Online booking available

$175 - $415
Per Night

$1225 - $2905
Per Week

Kaibo Yacht Club #20B

Cayman Kai
A popular boater’s destination and condo complex, Kaibo Yacht Club in Cayman Kai gathers locals and ...
Condo 2 / 2 / 6

*
Online booking available

$150 - $415
Per Night

$1050 - $2905
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

Sea Breeze 8

Seven Mile Beach
A stunning sunset show awaits you at Seabreeze 8. This 4-bedroom, 4.5-bath, 4th floor unit provides ...
Condo 4 / 4.5 / 10

*
Online booking available

$840 - $2164
Per Night

$5880 - $15150
Per Week

The Grandview 511

Grand Cayman
Ground floor corner unit with great natural light and an easy walk out to our beach, pool and garden...
Condo 2 / 2 / 6

*
Online booking available

$410 - $645
Per Night

$2870 - $4515
Per Week

05 Aqua Bay Club

Grand Cayman
Beautifully decorated 2 bedroom Tastefully decorated, fully equipped 2 bedroom, 2 bathroom ocean f...
Condo 2 / 2 / 6

*
Online booking available

$400 - $750
Per Night

$2800 - $5250
Per Week

Lacovia #6

Grand Cayman
Claim a prime spot on the beach at Lacovia, a small-scale beachfront resort in the heart of sought-a...
Condo 3 / 3 / 8

*
Online booking available

$315 - $875
Per Night

$2205 - $6125
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

Kailypso

Cayman Kai
Friends and families love this 3-bedroom, 2-bath beach house tucked into a private cove in a residen...
Villa 3 / 2 / 8

*
Online booking available

$395 - $835
Per Night

$2765 - $5845
Per Week

The Grandview 622

Grand Cayman
Corner unit layout offers fantastic second floor vistas of the palm-drenched gardens and Seven Mile ...
Condo 2 / 2 / 6

*
Online booking available

$410 - $645
Per Night

$2870 - $4515
Per Week

Shellen

East End
Tuck into your own private mini-resort at Shellen, a 3-bedroom (plus sleeper sofa), 2-bath villa poi...
Villa 3 / 2 / 8

*
Online booking available

$270 - $695
Per Night

$1890 - $4865
Per Week

Blossom Village Cottage

Little Cayman
Walk directly from your classic beach cottage to the palm-shaded beach in one-of-a-kind Little Cayma...
Villa 3 / 3 / 8

*
Online booking available

$225 - $620
Per Night

$1575 - $4340
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

Villas Pappagallo #22

West Bay
This lovely ground-floor beachfront one-bedroom villa with TWO Oceanfront patios is ideally located ...
Condo 1 / 1 / 4

*
Online booking available

$155 - $360
Per Night

$1085 - $2520
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

The Grandview 1212

Grand Cayman
A modern flair on this Caribbean haven with privacy and seclusion this is a great unit for those wan...
Condo 2 / 2 / 6

*
Online booking available

$500 - $735
Per Night

$3500 - $5145
Per Week

Kirk Kove

Cayman Kai
The spacious layout at Kirk Kove in Cayman Kai will surprise you. A 2-bedroom, 2-bath beach house fo...
Villa 2 / 2 / 6

*
Online booking available

$175 - $460
Per Night

$1225 - $3220
Per Week

The Grandview 121

Grand Cayman
This beach front unit is all about the views. The sun sets directly off the corner unit screened pat...
Condo 2 / 2 / 6

*
Online booking available

$500 - $735
Per Night

$3500 - $5145
Per Week

On The Rocks - Cayman

Frank Sound
Proudly resting on the Beach Bay bluff over the shimmering azure Caribbean waters. This beautiful On...
Villa 6 / 4 / 14

*
Online booking available

$800 - $1335
Per Night

$5600 - $9345
Per Week

Sunset Cove #104

Seven Mile Beach
At Sunset Cove Condo Resort, you get all the perks of a Caribbean resort—including the largest swimm...
Condo 3 / 2 / 8

*
Online booking available

$305 - $695
Per Night

$2135 - $4865
Per Week

 

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