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.

Cayman Islands

Check availability
Refine search

Refine Location

 

Desired stay

 

Price range

 
600 AUD13,550 AUD
 

Bedrooms

Studio10+
 

Bathrooms

14+
 

Sleeps

110+
 

Traveller rating

1.05.0
 

Property type

 

Amenities

 

Suitability

 
Own a rental property?
Want more exposure for your rental? Get listed in TripAdvisor Holiday Rentals (in partnership with FlipKey).
Holiday Rental Calculator
Compare & Save »
Free Newsletter

Sign up to hear about gorgeous holiday rentals, the latest deals, exciting destinations, and more.

Rental properties provided by
Learn more
Don't see the property you rented? Tell us more about it »

Vacation Rentals in 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
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.

 
more    
Rentals you can trust
Reviews by guests
Verified Listings
Most Trusted Travel Advice
Tip: Refine your search by price, amenities, & more (see left column).
Searching … 0% complete
261 Trusted Cayman Islands Rentals
List View
loading...
Showing 0 plottable rentals of 0 total
Map nearby restaurants, attractions & more
Restaurants
Things to Do

Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
Cayman Islands, Grand Cayman, George Town Holiday Rentals
Georgetown Villas Unit # 303 - Oceanfront Condo
Slideshow
4 of 5 stars 4 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
231 AUD
Week:
1,616 AUD - 2,258 AUD
Minimum rental - 3 nights
Check availability
Map unavailable
Cayman Islands, Grand Cayman, Seven Mile Beach Holiday Rentals
Ocean-front 2BR, direct walk to beach  #5
4 of 5 stars 4 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
334 AUD - 693 AUD
Minimum rental - 3 nights
Check availability
Map unavailable
Caribbean, Cayman Islands Holiday Rentals
Laurelei: Oceanfront Cayman Kai Condo
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Week:
1,652 AUD - 2,011 AUD
Minimum rental - 5 nights
Check availability
Show on map
Also consider
The Best of...
262 AUD / night
2 Bedrooms, sleeps 4
2 Bathrooms
OCEANFRONT...
180 AUD - 359 AUD / night
3 Bedrooms, sleeps 6
2 Bathrooms
Simply Cayman
1,847 AUD - 2,771 AUD / week
2 Bedrooms, sleeps 8
2 Bathrooms
Three Little...
369 AUD - 513 AUD / night
2 Bedrooms, sleeps 6
2 Bathrooms
Cayman Conch...
221 AUD - 272 AUD / night
2 Bedrooms, sleeps 6
2 Bathrooms
Caribbean, Cayman Islands Holiday Rentals
Harvey Nicole Kai: Oceanfront Condo
Slideshow
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Week:
1,796 AUD - 2,566 AUD
Minimum rental - 3 nights
Check availability
Map unavailable
Picturesque 2 Bedroom, 2 Bathroom House in Mont Tremblant (Le Plateau 232-3)
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 5
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
322 AUD - 364 AUD
Minimum rental - 2 nights
Check availability
Show on map
Caribbean, Cayman Islands Holiday Rentals
Mont Tremblant 2 BR/2 BA House (Altitude 170-4)
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 5
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
435 AUD - 503 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Caribbean, Cayman Islands, Grand Cayman Holiday Rentals
#27 Harbour Heights: Beachfront Beauty, Sleeps 6
Slideshow
4.5 of 5 stars 2 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
282 AUD - 503 AUD
Minimum rental - 5 nights
Check availability
Show on map
Cayman Islands, Grand Cayman, Seven Mile Beach Holiday Rentals
Beautifully decorated ocean-front 2BR condo #22
Slideshow
4 of 5 stars 5 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
334 AUD - 693 AUD
Minimum rental - 3 nights
Check availability
Map unavailable
Poinsettia #B4, Seven Mile Beach
Cayman Islands, Grand Cayman, Seven Mile Beach Holiday Rentals
Poinsettia #B4
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
294 AUD - 381 AUD
Week:
2,055 AUD - 2,670 AUD
Minimum rental - 1 night
Check availability
Show on map
The Islands Club Unit 10, Seven Mile Beach
Cayman Islands, Grand Cayman, Seven Mile Beach Holiday Rentals
The Islands Club Unit 10
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Special offer details »
Night:
431 AUD
Minimum rental - 5 nights
Check availability
Map unavailable
Caribbean, Cayman Islands Holiday Rentals
The Pools #10
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
366 AUD - 513 AUD
Week:
2,568 AUD - 3,595 AUD
Minimum rental - 1 night
Check availability
Show on map
Cayman Islands, Grand Cayman, Bodden Town Holiday Rentals
Divers Paradise Huge 3 Bed 3.5 Bath Townhouse
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 3 Bedrooms, sleeps 7
  • 4 Bathrooms
  • Owner
EMAIL OWNER
Night:
257 AUD - 303 AUD
Week:
1,616 AUD - 1,976 AUD
Month:
4,362 AUD - 6,158 AUD
Minimum rental - 3 nights
Check availability
Show on map
Caribbean, Cayman Islands Holiday Rentals
On The Bay #104
Slideshow
4.5 of 5 stars 7 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
198 AUD - 249 AUD
Week:
1,386 AUD - 1,746 AUD
Minimum rental - 3 nights
Check availability
Show on map
Caribbean Paradise 9, George Town
Cayman Islands, Grand Cayman, George Town Holiday Rentals
Caribbean Paradise 9
Slideshow
4 of 5 stars 2 reviews
  • Villa
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
476 AUD - 623 AUD
Week:
3,338 AUD - 4,366 AUD
Minimum rental - 1 night
Check availability
Show on map
Caribbean, Cayman Islands, Cayman Brac Holiday Rentals
Ocean Front Condominiums on Cayman Brac
Slideshow
4.5 of 5 stars 8 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
1,026 AUD
Month:
3,284 AUD
Minimum rental - 3 nights
Check availability
Show on map
Cayman Islands, Grand Cayman, George Town Holiday Rentals
Georgetown Villas Unit #113 - Oceanfront Condo
Slideshow
4.5 of 5 stars 6 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • Professional
EMAIL AGENT
Night:
257 AUD - 359 AUD
Week:
1,796 AUD - 2,566 AUD
Minimum rental - 3 nights
Check availability
Map unavailable

Cayman Islands Holiday Rental Advice

Secluded Sunsets Cayman Brac
Posted by DonnaMJW, 26 Nov 2011
... planning on staying in a vacation rental "Secluded Sunsets" on the north side, west end of the island. Until recently this rental was listed on Trip Adviser (with good reviews) but is now no longer listed. I'm wondering if anyone is familiar with this place, and if so how ... more
Posted by henrybarbera, 15 May 2012
im the owner of secluded sunsets - i have even more great reviews - in a year in a half i have more reviews then all guests houses in the caymans (including grand cayman) except for three properties. check out vacation rentals by owner, ... more
Anyone know anything about South Bay Beach Club?
Posted by AustinBeachy, 9 May 2011
... well and looking for a vacation rental for my family...SO confusing! Haven't been to Cayman since '81...not that many choices then. Couple of questions since I have a 7 and 15 year old looking for a nice big sandy beach. Is it rocky, wide, safe and convenient ... more
Another food question
Posted by GlassAli, 17 Jan 2012
We're staying at a vacation rental. I'm wondering the best way to handle groceries. Do you bring meats packed in dry ice? Do you shop on Grand Cayman before coming over? Do you check a bag with staples in it when coming from the states? I know the ... more
Best beach(es) and best place to stay in Grand Cayman Island
Posted by Testudo, 6 Apr 2011
... look under the "Hotels" or "vacation rental" section of this site for some info. There are non-native Green iguanas throughout the island and the native Blue iguanas mainly on the less developed East End and North Side districts. Iguanas don't normally bother people, but just like racoons at ... more
Posted by SeaweedSara, 3 Nov 2011
... have a kitchen or condo/vacation rental so that we may cook most meals. We are bringing our 5 year old son. We looked at Turtle club, The Reef Resort All Beach Front Suites, 3 points villa. We are unsure of what end of the island we should stay at ... more
london house
Posted by CaymanSunset, 21 Feb 2011
We own a vacation rental in West Bay and got an inquiry a few months ago from a family looking for last-minute accommodations because the London House unit where they were staying had a bug infestation. That said, I've always thought the property looked pretty nice from the ... more
Paradise Point Apartment
Posted by kiddos, 22 May 2011
That is more a residential area than one which attracts tourists. Are you looking for a vacation rental or a long term stay on the island? ... more
Posted by TLK0254, 22 May 2011
Looking for a budget vacation rental ... more
Finally booked the NS
Posted by CayManTA, 3 Feb 2011
... Those instructions lead to a vacation rental home in the Island Houses of Cayman Kai, which is across the street from Rum Point Club, one mile north of Kaibo Yacht Club, so the driving directions and odometer readings on that webpage will at least get you fairly close to wherever ... more