CARIBBEAN'S
best-kept secret

Some things are just
BETTER LEFT UNSHARED

THIS IS NO RESORT.
Goodbye cookie-cutter

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!

Ann Whiting

Office Manager & 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
I just wanted to let you know that we had a fantastic time at the Kaibo. The condo was wonderful. We had so much fun at the pool and beach. What a beautiful island. Thank you so much for all your help.
Alison
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.
Proud Member of:
  • Cayman Islands Tourism Association
  • Cayman Islands Chamber of Commerce
  • Licensed by: Cayman Islands Department of Tourism