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Vacation Rentals in Cayman Islands, Caribbean

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  • 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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All 366 Rentals in Cayman Islands
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From
$550
Per Night
West Bay
4 Bedrooms, 5 Bathrooms, Sleeps 8
10 photos Details
Reviews (2) Make Inquiry
From
$390
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
11 photos Details
Reviews (5) Make Inquiry
From
$390
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (7) Make Inquiry
Also consider
Barefoot Lagoon Island House
2 Bedrooms, sleeps 6
$250 - $400 / night
CaymanChillin, On the Sea,Grand Cayman, East End
3 Bedrooms, sleeps 6
$428 / night
"A Mid-Winter Night's Dream" - Direct Oceanfront!!
2 Bedrooms, sleeps 6
$230 - $290 / night
Cayman Islands Divers Paradise 1st Floor Oceanfront Condo
2 Bedrooms, sleeps 8
$163 - $253 / night
From
$395
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (3) Make Inquiry
From
$436
Per Night
Little Cayman
3 Bedrooms, 2 Bathrooms, Sleeps 9
14 photos Details
Reviews (4) Make Inquiry
From
$301
Per Night
Seven Mile Beach
2 Bedrooms, 3 Bathrooms, Sleeps 4
11 photos Details
Reviews (9) Make Inquiry
From
$550
Per Night
Grand Cayman
3 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (1) Make Inquiry
From
$195
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
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From
$330
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (12) Make Inquiry
From
$379
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (7) Make Inquiry
From
$473
Per Night
Little Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (3) Make Inquiry
From
$575
Per Night
Grand Cayman
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
From
$575
Per Night
Grand Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 6
11 photos Details
Reviews (6) Make Inquiry
From
$330
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (8) Make Inquiry
From
$425
Per Night
Studio, 1 Bathroom, Sleeps 4
49 photos Details
Reviews (1) Make Inquiry
From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
Reviews (1) Make Inquiry
From
$333
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (2) Make Inquiry
From
$392
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
7 photos Details
Reviews (11) Make Inquiry
From
$1,400
Per Week
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
94 photos Details
Reviews (27) Make Inquiry
From
$299
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
25 photos Details
Reviews (1) Make Inquiry
From
$480
Per Night
Seven Mile Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
14 photos Details
Reviews (6) Make Inquiry
From
$426
Per Night
George Town
3 Bedrooms, 3 Bathrooms, Sleeps 6
10 photos Details
Reviews (8) Make Inquiry
From
$315
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (5) Make Inquiry
From
$315
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (1) Make Inquiry
From
$921
Per Night
Bodden Town
4 Bedrooms, 4 Bathrooms, Sleeps 10
26 photos Details
Reviews (3) Make Inquiry
From
$250
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
35 photos Details
Reviews (3) Make Inquiry
From
$550
Per Night
Gun Bay
4 Bedrooms, 4 Bathrooms, Sleeps 10
24 photos Details
Reviews (9) Make Inquiry
From
$340
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
8 photos Details
Reviews (1) Make Inquiry
From
$500
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
Reviews (3) Make Inquiry
From
$921
Per Night
Bodden Town
4 Bedrooms, 4 Bathrooms, Sleeps 12
39 photos Details
Reviews (7) Make Inquiry
From
$215
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (6) Make Inquiry
From
$315
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Reviews (2) Make Inquiry
From
$220
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 5
19 photos Details
Reviews (3) Make Inquiry
From
$340
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
8 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
George Town
2 Bedrooms, Sleeps 6
47 photos Details
Reviews (10) Make Inquiry
From
$196
Per Night
Old Man Bay
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (14) Make Inquiry
From
$250
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (1) Make Inquiry
From
$335
Per Night
North Side
3 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
Reviews (3) Make Inquiry
From
$300
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (16) Make Inquiry
From
$265
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 5
44 photos Details
Reviews (7) Make Inquiry
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Book Online(141)

Suitability

  • Wheelchair access (27)
  • Elder access (97)
  • Suitable for children (129)
  • Pet friendly (10)
  • Smoking allowed (5)

Amenities

  • Air Conditioning (321)
  • Grill (243)
  • Washer/Dryer (243)
  • Other outdoor space (232)
  • All pools (218)
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Book Online(141)

Suitability

  • Wheelchair access (27)
  • Elder access (97)
  • Suitable for children (129)
  • Pet friendly (10)
  • Smoking allowed (5)

Amenities

  • Air Conditioning (321)
  • Grill (243)
  • Washer/Dryer (243)
  • Other outdoor space (232)
  • All pools (218)
  • View all amenities
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.