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.

Vacation Rentals in Cayman Islands, Caribbean

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 355 Rentals in Cayman Islands
loading...
Sort by
From
$2,000
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 8
16 photos Details
Make Inquiry
From
$691
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 8
13 photos Details
Make Inquiry
From
$1,100
Per Week
1 Bedroom, 1 Bathroom, Sleeps 4
6 photos Details
Make Inquiry
Also consider
Vitamin Sea at Coral Bay Beachfront Grand Cayman (Owner pays Govt Tax not Guest)
2 Bedrooms, sleeps 6
$214 - $356 / night
Conquered Fame - Cayman Island Escape
4 Bedrooms, sleeps 10
$500 - $750 / night
"A Mid-Winter Night's Dream" - Direct Oceanfront!!
2 Bedrooms, sleeps 6
$230 - $290 / night
Villa Habana,  Cayman Islands
2 Bedrooms, sleeps 4
$295 - $475 / night
From
$509
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Make Inquiry
From
$363
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
Reviews (7) Make Inquiry
From
$545
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (11) Make Inquiry
From
$291
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (3) Make Inquiry
From
$582
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Inquiry
Get the List
From
$291
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (11) Make Inquiry
From
$203
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
8 photos Details
Reviews (2) Make Inquiry
From
$691
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details
Reviews (3) Make Inquiry
From
$1,014
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
15 photos Details
Reviews (5) Make Inquiry
From
$2,065
Per Night
7 Bedrooms, 6 Bathrooms, Sleeps 14
22 photos Details
Make Inquiry
From
$1,604
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 15
24 photos Details
Reviews (4) Make Inquiry
From
$203
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
Reviews (9) Make Inquiry
From
$333
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (3) Make Inquiry
From
$2,021
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 12
20 photos Details
Reviews (5) Make Inquiry
From
$1,128
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 11
18 photos Details
Make Inquiry
From
$225
Per Night
Grand Cayman
3 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
Reviews (5) Make Inquiry
From
$125
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
14 photos Details
Reviews (2) Make Inquiry
From
$1,700
Per Night
Grand Cayman
7 Bedrooms, 7 Bathrooms, Sleeps 18
23 photos Details
Reviews (3) Make Inquiry
From
$300
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (19) Make Inquiry
From
$450
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 7
14 photos Details
Reviews (16) Make Inquiry
From
$840
Per Night
Grand Cayman
4 Bedrooms, 4 Bathrooms, Sleeps 12
21 photos Details
Reviews (5) Make Inquiry
From
$180
Per Night
Grand Cayman
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
Make Inquiry
From
$465
Per Night
Grand Cayman
4 Bedrooms, 4 Bathrooms, Sleeps 12
16 photos Details
Reviews (2) Make Inquiry
From
$570
Per Night
Grand Cayman
3 Bedrooms, 4 Bathrooms, Sleeps 6
13 photos Details
Reviews (3) Make Inquiry
From
$1,850
Per Night
Grand Cayman
5 Bedrooms, 6 Bathrooms, Sleeps 14
22 photos Details
Reviews (8) Make Inquiry
From
$385
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
70 photos Details
Make Inquiry
From
$225
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
7 photos Details
Reviews (16) Make Inquiry
From
$175
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Make Inquiry
From
$475
Per Night
Grand Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 8
33 photos Details
Reviews (13) Make Inquiry
From
$571
Per Night
Grand Cayman
4 Bedrooms, 4 Bathrooms, Sleeps 10
28 photos Details
Reviews (10) Make Inquiry
From
$275
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
18 photos Details
Reviews (40) Make Inquiry
From
$225
Per Night
Grand Cayman
2 Bedrooms, 3 Bathrooms, Sleeps 6
16 photos Details
Reviews (15) Make Inquiry
From
$1,000
Per Night
Grand Cayman
5 Bedrooms, 5 Bathrooms, Sleeps 12
35 photos Details
Make Inquiry
From
$650
Per Night
Grand Cayman
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Make Inquiry
From
$995
Per Night
Grand Cayman
5 Bedrooms, 4 Bathrooms, Sleeps 10
17 photos Details
Reviews (4) Make Inquiry
From
$2,125
Per Night
Grand Cayman
6 Bedrooms, 6 Bathrooms, Sleeps 14
15 photos Details
Reviews (7) Make Inquiry
From
$1,185
Per Night
Grand Cayman
5 Bedrooms, 4 Bathrooms, Sleeps 10
16 photos Details
Make Inquiry
Go to map view
Book Online(188)
Use filters to find the best results!

Suitability

  • Wheelchair access (33)
  • Elder access (105)
  • Suitable for children (151)
  • Pet friendly (13)
  • Smoking allowed (11)

Amenities

  • Air Conditioning (322)
  • Internet (260)
  • Other outdoor space (239)
  • Grill (196)
  • All pools (187)
  • 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

More Romance destinations:

More Beach destinations:

More Caribbean & Mexico destinations:

Filter search results by:
Book Online(188)

Suitability

  • Wheelchair access (33)
  • Elder access (105)
  • Suitable for children (151)
  • Pet friendly (13)
  • Smoking allowed (11)

Amenities

  • Air Conditioning (322)
  • Internet (260)
  • Other outdoor space (239)
  • Grill (196)
  • All pools (187)
  • 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.