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Cayman Islands

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Cayman Islands Vacation Rentals

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Cayman Island Beachfront Vacation Villas and Condo Rentals

As an international destination for the affluent, Grand Cayman offers a broad selection of vacation rentals. Luxury condo and villa rentals have emerged as an extremely popular choice for visitors to the aqua paradise surrounding the Cayman Islands. You may choose a comfortable waterfront condo for your romantic escape or a family-friendly beachside villa overlooking the silky sands of Grand Cayman. You and your family will welcome the privacy, space, upscale amenities and freedom to ‘do your own thing.’

Attractions and activities in the Cayman Islands

Whether you seek a pampered holiday complete with spas and constant high-end dining and shopping or a laid back, loll-in-the-hammock seashore vacation; you’ll not be disappointed in the variety of activities the islands offer. The Cayman Islands include three islands with unique landscapes, rhythms and activities. The largest and most vivacious is the Grand Cayman, home to sophisticated financiers, high-end designer boutiques and a broad spectrum of dining options. Water sports take the central spotlight for popular activities – from jet skiing, parasailing and fishing to swimming with sea creatures, diving and meandering along the miles of pure, white sands. Seaside golfing and discovering the protected ecosystem along the Mastic Trail also are popular. And the Queen Elizabeth II Botanic Park provides 65 spectacular acres of rare flora and fauna.

Snorkeling

Cayman Brac and Little Cayman are the smaller Cayman Islands that attract snorkelers, divers and those who embrace the serene pace of life, apart from lively Grand Cayman. Little Cayman offers a unique landscape along its 12-mile by 1-mile stretches, where The Bluff rises to 140 feet above sea level to the east (Brac is Gaelic for Bluff). Diving adventures range from Little Cayman’s calm, reef-protected sounds to daring dives to sunken ships and soaring underwater limestone formations.

Confident choices for waterfront vacation rentals

While the largest offering of luxury rentals is available on Grand Cayman, one magnificent Cayman Brac rental home features an incomparable 330 feet of private beachfront and acres of lovely old sea grape, thatch palm and almond tree forests. Condo and beachfront villa rentals vary in size and provide every convenience of home to welcome guests. In what can be an expensive destination, vacation rentals cut holiday costs by allowing a mix of home-cooked meals and dining excursions. With complete information, numerous photos and unbiased guest reviews, you can choose your rental with absolute confidence.

 
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$190 - $260 / night
2 Bedrooms, sleeps 6
2 Bathrooms
$250 - $375 / night
2 Bedrooms, sleeps 6
3 Bathrooms
$775 - $975 / night
4 Bedrooms, sleeps 8
4 Bathrooms
$340 - $520 / night
2 Bedrooms, sleeps 4
3 Bathrooms
$1,700 / week
3 Bedrooms, sleeps 6
2 Bathrooms

Traveler Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$325 - $675
Minimum rental - 3 nights
Check availability
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  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$420 - $670
Minimum rental - 5 nights
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$420 - $670
Minimum rental - 5 nights
Check availability
Map unavailable
Also consider
$190 - $260 / night
2 Bedrooms, sleeps 6
2 Bathrooms
$250 - $375 / night
2 Bedrooms, sleeps 6
3 Bathrooms
$775 - $975 / night
4 Bedrooms, sleeps 8
4 Bathrooms
$340 - $520 / night
2 Bedrooms, sleeps 4
3 Bathrooms
$1,700 / week
3 Bedrooms, sleeps 6
2 Bathrooms
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$325 - $675
Minimum rental - 3 nights
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$300 - $450
Week:
$2,102 - $3,153
Minimum rental - 1 night
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$225
Week:
$1,575 - $2,200
Minimum rental - 3 nights
Check availability
Map unavailable
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$414 - $557
Week:
$2,902 - $3,903
Minimum rental - 1 night
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • Professional
EMAIL MANAGER
Night:
$250 - $350
Week:
$1,750 - $2,500
Minimum rental - 3 nights
Check availability
Map unavailable
Caribbean, Cayman Islands Vacation Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$225
Week:
$1,400 - $2,500
Minimum rental - 3 nights
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Check availability
Map unavailable
Caribbean, Cayman Islands Vacation Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Week:
$1,610 - $1,960
Minimum rental - 5 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
$1,000
Month:
$3,200
Minimum rental - 3 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
$215 - $315
Week:
$1,400 - $2,100
Month:
$4,200 - $5,000
Minimum rental - 5 nights
Check availability
  • Villa
  • 4 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$779 - $1,001
Week:
$5,455 - $7,007
Minimum rental - 1 night
Check availability
Map unavailable
  • Villa
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
$450 - $525
Minimum rental - 3 nights
Check availability

Cayman Islands Vacation Rental Advice

Posted by 7miler, Jan 14, 2012
... and book it. You even get an instant confirmation! Huge time saver and WAY easier than wading through the many pages of vacation rentals here. I recently booked a unit at The Renaissance this way (it looks awesome!!) and it was sooo easy! Received confirmation directly from the property too ... more
Posted by lvallecilloky, Nov 22, 2011
Yes you may, check out Paradise Properties Vacation Rentals here: http://paradisepropertiescayman.com/index.php?option=com_joomanager&view=itemslist&catid=49&Itemid=141 ... more
Posted by onthegoIllinois, Oct 16, 2011
... 2012 and deciding between two vacation rentals. One is on the North side and the other on the South side. Anyone know the "preferred" area? I'm sure it's beautiful either side, but wanted to hear from anyone that has been there. We don't dive, but love the ... more
Posted by NorthSideSue, Sep 11, 2011
... beach there. The closest grocery would be the Fosters in Savannah, about a 12-15 minute drive. I see that the Turtle Nest Inn just added this property to their list of vacation rentals. They have a goof reputation, so I'm assuming this unit is in pretty good shape ... more
Posted by Testudo, Aug 17, 2011
... com/offshoresnorkeling.htm Some places to consider are: Far Tortuga Villa and the surrounding homes Mahogany Point Condos Northern Lights Condos The Retreat Condos and surrounding villas Shellen and Laughing Waters Villas and others nearby. http://www.grandcaymanvillas.net/ http://www.caymanvillas.com/cayman-islands-vacation-rentals-property-14-19 ... more
Posted by kiddos, May 12, 2011
... did not know they offered vacation rentals at all. It has always been a mystery to me. It is the only gated complex in that area, the units are set back far from the road for privacy. I always thought of it as an exclusive property and have never ventured ... more
Posted by Testudo, Apr 29, 2011
... here on Trip Advisor's Vacation Rentals. Those closer to or in George Town, West Bay and East End or North Side tend to cost less than right on Seven Mile Beach. Some super cheap non-condo options by Cayman standards are: Eldemire Guest House: http://eldemire.com/ Harbour View ... more
Posted by AustinBeachy, May 9, 2011
... well and looking for a vacation rental for my family...SO confusing! Haven't been to Cayman since '81...not that many choices then. Couple of questions since I have a 7 and 15 year old looking for a nice big sandy beach. Is it rocky, wide, safe and convenient ... more
Posted by GlassAli, Jan 17, 2012
We're staying at a vacation rental. I'm wondering the best way to handle groceries. Do you bring meats packed in dry ice? Do you shop on Grand Cayman before coming over? Do you check a bag with staples in it when coming from the states? I know the ... more
Posted by DonnaMJW, Nov 26, 2011
... planning on staying in a vacation rental "Secluded Sunsets" on the north side, west end of the island. Until recently this rental was listed on Trip Adviser (with good reviews) but is now no longer listed. I'm wondering if anyone is familiar with this place, and if so how ... more
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