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Vacation Rentals in Cayman Islands, Caribbean

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  • 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
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320 Trusted Cayman Islands Rentals
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Beachfront, 7 Mil... , Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Beachfront, 7 Mile Beach, Discovery Point Club to your Saves list
from
$325
Per Night
2 Bedrooms, Sleeps 6
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You added Georgetown Villas Unit # 203 - Oceanfront Condo to your Saves list
from
$279
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Georgetown Villas Unit # 303 - Oceanfront Condo to your Saves list
from
$225
Per Night
Also consider
Retreat #33, Beachfront on tropical Rum Point
$320 - $450 / night
2 Bedrooms, sleeps 6
3 Bathrooms
Ocean Wave: Cobalt
$122 - $165 / night
2 Bedrooms, sleeps 4
2 Bathrooms
#11 Harbour Heights-Perfect Family Beach Getaway
$315 - $490 / night
2 Bedrooms, sleeps 5
2 Bathrooms
CaymanChillin, On the Sea,Grand Cayman, East End
$428 / night
3 Bedrooms, sleeps 6
2 Bathrooms
4 Bedrooms, 4 Bathrooms, Sleeps 10
from
$750
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$250
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
from
$130
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Save
You added Summer rates now at Cayman's "best kept secret" to your Saves list
from
$450
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Cayman Conch Quest Beachfront Condo in Rum Point to your Saves list
from
$215
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 9
from
$375
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Tastefully decora... , Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Tastefully decorated 2BR condo, direct walk to beach #7 to your Saves list
from
$330
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
from
$420
Per Night
On The Bay #311 , Old Man Bay
3 Bedrooms, 3 Bathrooms, Sleeps 6
from
$892
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
from
$295
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Three Little Birds -2BR+ Villa, Private Beach to your Saves list
from
$360
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
On The Bay #104 , Old Man Bay
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$196
Per Night
Casa Caribe #3 , Grand Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 6
from
$575
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 10
from
$650
Per Night
2BR at Aqua Bay C... , Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$330
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Beachfront privac... , Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Beachfront privacy - 10 minutes to George Town to your Saves list
from
$214
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 7
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You added Divers Paradise Huge 3 Bed 3.5 Bath Townhouse to your Saves list
from
$250
Per Night
2BR-Cayman Dream , Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 8
from
$425
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
from
$171
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Ocean Wave: Azure , Cayman Brac
2 Bedrooms, 2 Bathrooms, Sleeps 4
from
$150
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 4
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You added Looking for endless Seafront views? Try SS 24! to your Saves list
from
$260
Per Night
3 Bedrooms, 5 Bathrooms, Sleeps 8
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You added Caymanease A New Oceanfront Villa With A Pool to your Saves list
from
$657
Per Night
Little Cayman Escape , Little Cayman
3 Bedrooms, 2 Bathrooms, Sleeps 9
from
$436
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
from
$325
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
from
$424
Per Night
4 Bedrooms, 1 Bathroom, Sleeps 1
from
$570
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
from
$260
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Vitamin Sea at Coral Bay Beachfront Grand Cayman to your Saves list
from
$214
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Cayman Brac Paradise w 330ft of private oceanfront to your Saves list
from
$242
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added "A Mid-Winter Night's Dream" - Direct Oceanfront!! to your Saves list
from
$230
Per Night
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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