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CARIBBEAN'S
best-kept secret

Why Choose Us

Top-Rated Properties

Choose your dream vacation! We offer a selective portfolio of the Cayman Islands’ most splendid beachfront properties and hidden gems. Discover sunset views, secluded beaches, stylish design and ideal locations in a range of price points.
Trusted In Cayman Since 1970

Leave your to-do list at home and enjoy the view. Our island-based crew is available 24/7 to help you ditch stress and have fun on your vacation. We’ve helped 20,000 satisfied guests find their tropical tranquility over the last 50 years. Let us add you to that list!
Cayman Travel Experts

Our Cayman Islands experts will be your vacation gurus, from choosing the perfect rental to filling your schedule with the best local events, meals, and adventures. Live like a local with our Caymans expertise!

Jennie Cairns

Concierge & Travel Specialist

Concierge Service

From landing to “goodbyes,” your personal Cayman concierge is the ultimate partner in shaping a by-the-sea experience you won’t forget.

Looking to host a special event on our special islands? Cayman Villas will help plan your dream wedding, honeymoon, or any occasion deserving of a proper Caymanian celebration!

Learn more
We had A GREAT time! Truly it was the best vacation either of us has had in years... the cottage was great and we loved Little Cayman. We will definitely be back.
Dario
We have been involved from the beginning with Penny Cumber and Cayman Villas. It has always been a pleasure as Penny is one of the most honest, professional, precise and patient ( as I have not always been as proficient as she always is), and she keeps meticulous records of phone calls, emails, letters and has helped me in the past on the financial reports when I have lost figures. Penny has cared for her clients, checks her properties to insure they are in the ready and in the best condition. There has never been one problem between us since the beginning which is a very glowing recommendation.
I have two properties that I let through Cayman Villas. I’m very happy with the service they provide: they have a long reach into the North American market and are responsive, helpful and full of good suggestions to help me get the best out of my investments. Their account reporting  is clear, and the punctuality and accuracy of their monthly rent transfers takes all the stress out of the money side of the operation. As an owner, I can’t recommend Cayman Villas highly enough.
Proud Member of:
  • Cayman Islands Tourism Association
  • Cayman Islands Chamber of Commerce
  • Licensed by: Cayman Islands Department of Tourism