We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Villas Cayman Islands, Caribbean

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
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 374 Rentals in Cayman Islands
loading...
Sort by
From
$341
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (19) Make Enquiry
From
$303
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (11) Make Enquiry
From
$346
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (1) Make Enquiry
Also consider
Featherstone's House of the Rising Sun
1 Bedroom, sleeps 3
$137 - $152 / night
Central Luxury Condo across from Beach in Cayman!
3 Bedrooms, sleeps 6
$346 - $559 / night
Amazing Cayman - Grand Cayman Island Condo Rentals
1 Bedroom, sleeps 4
$186 / night
Oceanfront Luxury! WiFi, Cable, Diving, Free Calling to US and Canada
2 Bedrooms, sleeps 6
$212 - $346 / night
From
$335
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
Reviews (4) Make Enquiry
From
$293
Per Night
Seven Mile Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (13) Make Enquiry
From
$216
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
Reviews (9) Make Enquiry
From
$1,708
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 15
24 photos Details
Reviews (3) Make Enquiry
From
$668
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
33 photos Details
Reviews (2) Make Enquiry
Get the List
From
$799
Per Night
Grand Cayman
4 Bedrooms, 4 Bathrooms, Sleeps 10
23 photos Details
Reviews (3) Make Enquiry
From
$234
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Reviews (2) Make Enquiry
From
$282
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 5
44 photos Details
Reviews (7) Make Enquiry
From
$240
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 4
7 photos Details
Reviews (16) Make Enquiry
From
$240
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
16 photos Details
Reviews (15) Make Enquiry
From
$181
Per Night
North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
27 photos Details
Reviews (10) Make Enquiry
From
$532
Per Night
Grand Cayman
4 Bedrooms, 2 Bathrooms, Sleeps 10
13 photos Details
Reviews (14) Make Enquiry
From
$456
Per Night
East End
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (22) Make Enquiry
From
$242
Per Night
West Bay
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (12) Make Enquiry
From
$692
Per Night
Seven Mile Beach
3 Bedrooms, 3 Bathrooms, Sleeps 7
24 photos Details
Reviews (3) Make Enquiry
From
$245
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (16) Make Enquiry
From
$209
Per Night
Old Man Bay
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (15) Make Enquiry
From
$302
Per Night
Old Man Bay
3 Bedrooms, 3 Bathrooms, Sleeps 6
12 photos Details
Reviews (7) Make Enquiry
From
$266
Per Night
West Bay
3 Bedrooms, 4 Bathrooms, Sleeps 6
31 photos Details
Reviews (8) Make Enquiry
From
$532
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
Reviews (3) Make Enquiry
From
$351
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (8) Make Enquiry
From
$756
Per Night
Little Cayman
4 Bedrooms, 3 Bathrooms, Sleeps 10
11 photos Details
Reviews (3) Make Enquiry
From
$266
Per Night
Old Man Bay
3 Bedrooms, 3 Bathrooms, Sleeps 6
34 photos Details
Reviews (10) Make Enquiry
From
$160
Per Night
Cayman Brac
2 Bedrooms, 3 Bathrooms, Sleeps 4
10 photos Details
Reviews (9) Make Enquiry
From
$319
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (18) Make Enquiry
From
$362
Per Night
Seven Mile Beach
2 Bedrooms, 3 Bathrooms, Sleeps 4
38 photos Details
Reviews (5) Make Enquiry
From
$426
Per Night
West Bay
3 Bedrooms, 3 Bathrooms, Sleeps 9
24 photos Details
Reviews (8) Make Enquiry
From
$160
Per Night
North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (3) Make Enquiry
From
$240
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
20 photos Details
Reviews (28) Make Enquiry
From
$319
Per Night
George Town
2 Bedrooms, Sleeps 6
47 photos Details
Reviews (11) Make Enquiry
From
$351
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (6) Make Enquiry
From
$144
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (45) Make Enquiry
From
$266
Per Night
West Bay
3 Bedrooms, 4 Bathrooms, Sleeps 7
24 photos Details
Reviews (28) Make Enquiry
From
$240
Per Night
Old Man Bay
2 Bedrooms, 3 Bathrooms, Sleeps 4
25 photos Details
Reviews (9) Make Enquiry
From
$229
Per Night
Old Man Bay
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (9) Make Enquiry
From
$851
Per Night
Grand Cayman
5 Bedrooms, 5 Bathrooms, Sleeps 12
32 photos Details
Reviews (10) Make Enquiry
From
$250
Per Night
West Bay
3 Bedrooms, 4 Bathrooms, Sleeps 7
10 photos Details
Reviews (5) Make Enquiry
Go to map view
Book Online(145)
Use filters to find the best results!

Suitability

  • Wheelchair access (34)
  • Elder access (103)
  • Suitable for children (138)
  • Pet friendly (11)
  • Smoking allowed (3)

Amenities

  • Air Conditioning (329)
  • Internet (288)
  • Other outdoor space (222)
  • Grill (207)
  • All pools (170)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
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.