Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Condos
Cottages
Estates
Hotels
Homes
Lodges
Studios
Townhomes
Villas
Barns
Boats
Cabins
Castles
Chalets
Farmhouses
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Cayman Islands Villa Rentals(119)

119 Results
$1,064 - $1,993
per night
5 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 11
5 - 7 night minimum stay
(18)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 5 night minimum stay
(21)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(15)
$100 - $180
per night
5 - 6 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 6 night minimum stay
(20)
$299 - $814
per night
1 - 5 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
1 - 5 night minimum stay
(7)
$1,700 - $2,850
per night
5 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
5 night minimum stay
(13)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
6 night minimum stay
(62)
$995 - $1,625
per night
5 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
5 night minimum stay
1 Review
$2,125 - $3,450
per night
5 night minimum stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
5 night minimum stay
(3)
$1,850 - $3,100
per night
5 night minimum stay
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 14
5 night minimum stay
(13)
$380 - $550
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(11)
$775 - $1,135
per night
5 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
5 night minimum stay
(4)
$1,707 - $2,707
per night
5 - 7 night minimum stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 14
5 - 7 night minimum stay
$1,700 - $2,850
per night
5 night minimum stay
  • 6 BR,
  • 7 BA,
  • Sleeps 16
5 night minimum stay
$454 - $710
per night
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 7 night minimum stay
$450 - $1,525
per night
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 7 night minimum stay
$1,012 - $1,499
per night
5 - 7 night minimum stay
  • 5 BR,
  • 6 BA,
  • Sleeps 11
5 - 7 night minimum stay
$1,914 - $3,318
per night
5 - 7 night minimum stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
5 - 7 night minimum stay
$956 - $1,470
per night
5 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 7 night minimum stay
$650 - $1,850
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
5 - 7 night minimum stay
(11)
$450 - $725
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
1 Review
$457 - $514
per night
5 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
(3)
$3,200 - $9,500
per night
4 - 8 night minimum stay
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
4 - 8 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
5 night minimum stay
(3)
$995 - $1,995
per night
5 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 8
5 night minimum stay
(36)
$780 - $1,350
per night
5 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
5 night minimum stay
(19)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night minimum stay
(5)
$990 - $1,990
per night
5 night minimum stay
  • 7 BR,
  • 7 BA,
  • Sleeps 18
5 night minimum stay
2 Reviews
 

Recent Cayman Islands Reviews

Heaven on Earth

5 of 5
If you are looking to immerse yourself in a luxurious getaway and truly get away from it all, with your own private beach, in a tropical paradise then look no further. This would be an amazing experience for couples, families, or friends wanting a turnkey, high end, private home on one of the most beautiful beaches in the world, and would satisfy even the most discerning travelers. Here you will find a beautiful, luxurious, tranquil, and immaculately maintained home that comes with all the comforts one could ask for and more. I would recommend this home to anyone wanting to experience paradise in the tropics.
  • Submitted: Oct 15, 2014
  • Stayed: Aug 2014

So perfect

5 of 5
Our stay at Ocean Oasis was perfect. We stayed at this wonderful home for a girls only get away however I would not hesitate to bring my extended family and small children because there is plenty of room. The house was well equipped to meet all of our needs. We enjoyed cooking a few meals and even cracked into a coconut from a backyard palm tree. All 4 of the bedrooms were beautifully decorated and so comfortable. Waking up and seeing the ocean from our bed was the highlight of my trip. Staying at this house was like being on a private island with the perk of having restaurants and activities a very short drive from the front door. We did not see another human being on the beach our entire stay. The kayaking and snorkeling was great and we enjoyed watching all of the fish, lobsters, conchs and we even saw a barracuda. The owner, Tina, was beyond helpful in preparing us for our trip. From where and when to get groceries to great restaurant recommendations. We were glad we followed Tina’s advice and brought water shoes. We used them at the house, Rum Point and even Seven Mile. Thank you, Tina for letting us stay in your home and we look forward to returning next year.
  • Submitted: Sep 29, 2014
  • Stayed: Sep 2014

Great stay in Cayman Chillin'!

5 of 5
There were three couples and we had plenty of room and everything we needed for a great vacation! This home was close to restaraunts and a small grocery store so if we needed something it was easy to get. Bill was very informative and answered all our questions before our arrival. We highly recommend staying at CaymanChillin. We hope to make it back there one day!
  • Submitted: Sep 13, 2014
  • Stayed: Aug 2014