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 340 Rentals in Cayman Islands
loading...
Sort by
From
$327
Per Night
Little Cayman
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (4)
From
$799
Per Night
Grand Cayman
5 Bedrooms, 5 Bathrooms, Sleeps 12
32 photos Details
Reviews (10)
From
$264
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (10)
Also consider
View of the Ocean from every room / Pool & Hot Tub
2 Bedrooms, sleeps 6
$150 / night
Luxury Oceanfront Condos on Cayman Brac
2 Bedrooms, sleeps 6
$135 / night
Ocean Wave: Indigo
1 Bedroom, sleeps 2
$111 - $147 / night
CAYMAN COTTAGE - Located on the
1 Bedroom, sleeps 3
$140 / night
From
$467
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (7)
From
$330
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (8)
From
$454
Per Night
Grand Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details
Reviews (1)
From
$582
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
13 photos Details
Reviews (7)
From
$575
Per Night
Grand Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 6
13 photos Details
Reviews (1)
From
$203
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
8 photos Details
Reviews (14)
From
$473
Per Night
Little Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (3)
From
$426
Per Night
George Town
3 Bedrooms, 3 Bathrooms, Sleeps 6
10 photos Details
Reviews (8)
From
$330
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (13)
From
$575
Per Night
Grand Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details
Reviews (4)
From
$285
Per Night
Little Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
23 photos Details
Reviews (1)
From
$129
Per Night
Cayman Brac
1 Bedroom, 1 Bathroom, Sleeps 3
5 photos Details
Reviews (3)
From
$550
Per Night
West Bay
4 Bedrooms, 5 Bathrooms, Sleeps 8
10 photos Details
Reviews (4)
From
$425
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details
Reviews (3)
From
$291
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (1)
From
$125
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
14 photos Details
Reviews (1)
From
$995
Per Night
Grand Cayman
5 Bedrooms, 6 Bathrooms, Sleeps 10
17 photos Details
Reviews (7)
From
$390
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (5)
From
$114
Per Night
Cayman Brac
3 Bedrooms, 1 Bathroom, Sleeps 6
16 photos Details
Reviews (6)
From
$215
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (6)
From
$550
Per Night
Gun Bay
4 Bedrooms, 4 Bathrooms, Sleeps 10
24 photos Details
Reviews (12)
From
$213
Per Night
Old Man Bay
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (15)
From
$220
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 5
19 photos Details
Reviews (4)
From
$355
Per Night
Seven Mile Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
28 photos Details
Reviews (11)
From
$538
Per Night
East End
3 Bedrooms, 2 Bathrooms, Sleeps 8
16 photos Details
Reviews (7)
From
$450
Per Night
Seven Mile Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
11 photos Details
Reviews (11)
From
$500
Per Night
Grand Cayman
3 Bedrooms, 4 Bathrooms, Sleeps 6
24 photos Details
Reviews (1)
From
$850
Per Night
Old Man Bay
5 Bedrooms, 5 Bathrooms, Sleeps 14
23 photos Details
Reviews (10)
From
$275
Per Night
North Side
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
10 photos Details
Reviews (5)
From
$250
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
35 photos Details
Reviews (4)
From
$390
Per Night
Grand Cayman
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (4)
From
$600
Per Night
Little Cayman
3 Bedrooms, 3 Bathrooms, Sleeps 7
8 photos Details
Reviews (1)
From
$340
Per Night
Seven Mile Beach
2 Bedrooms, 3 Bathrooms, Sleeps 6
7 photos Details
Reviews (1)
From
$315
Per Night
Seven Mile Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (5)
From
$480
Per Night
Seven Mile Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
14 photos Details
Reviews (8)
From
$225
Per Night
Grand Cayman
1 Bedroom, 1 Bathroom, Sleeps 4
29 photos Details
Reviews (11)
From
$150
Per Night
Cayman Brac
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
5 photos Details
Reviews (2)
Go to map view
Book Online(169)
Use filters to find the best results!

Suitability

  • Wheelchair access (31)
  • Elder access (103)
  • Suitable for children (137)
  • Pet friendly (12)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (308)
  • Internet (261)
  • Other outdoor space (231)
  • Grill (186)
  • All pools (176)
  • 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

More Romance destinations:

More Beach destinations:

More Caribbean & Mexico destinations:

Filter search results by:
Book Online(169)

Suitability

  • Wheelchair access (31)
  • Elder access (103)
  • Suitable for children (137)
  • Pet friendly (12)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (308)
  • Internet (261)
  • Other outdoor space (231)
  • Grill (186)
  • All pools (176)
  • 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.