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WHO WE ARE

We are your island-based travel experts. Welcome to Cayman!

Why Choose Us

Cayman Villas has spent the last 45 years creating unforgettable vacations for over 20,000 happy guests. Passion for this special place drives our island-based team to share Cayman knowledge and introduce our guests to hand-picked properties in paradise. The result? A personalized Caribbean vacation for your whole family!
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Enjoy an on-island travel partner

We believe in connecting with our clients and supporting the Cayman community. Which is why, unlike most companies, our formula is “in Cayman, for Cayman.” We know our islands. After all, it’s where we live work, and play! We’ll show you a vacation that goes far beyond the cliché activities—from sun-drenched afternoon adventures to nights out on the town.
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Highly qualified local travel agents

The experts at Cayman Villas will guide you step by step through planning your dream Caribbean vacation. From the smallest detail to the biggest adventure. Let us help you find the perfect condo, villa, bungalow, or cabin to match your needs, budget and great expectations!
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Quality, quantity, possibilities

Chose from the Cayman Islands’ most sought-after beachfront properties. We offer a diverse selection of prices, features, locations, styles and sizes. No matter your choice, peace of mind, comfort and “wows” are guaranteed!

Our Team

Meet Cayman Islands' best vacation rental management team

Penny Cumber

Founder Managing Director
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Penny Cumber


Untamed traveller, dream chaser and devoted grandmother, Penny Cumber has spent no less than 45 years taking care of visitors and building her now well-established other baby, Cayman Villas.

“Renting your own beach house wasn’t much of a trend back then”, she remembers. “But we always kept doing what we loved, and here we are now!”.

You may catch Penny singing by the beach, playing with her grandchildren, or giving you a lesson you’ll remember at tennis.

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Jennie Cairns

Concierge & Travel Specialist
 

Jennie Cairns


Interior designer by training and originally from Montana USA, Ann Whiting has been living her travel industry passion through many areas and for many years.

From 10 years in the the ski industry as Guest Services Manager to being a New York city Personal Assistant to celebrities that we aren’t going to name-drop here, Ann finally chose to cast the anchor under the sun, on the beautiful beaches of Cayman Islands.

And we are glad she did!

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Noelle Kelly

Travel Specialist
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Noelle Kelly


Originally from Ireland, Noelle initially came to Cayman Islands for a little nine-month vacation. And here she is, 22 years later, with a family of her own.

With over 20 years of experience in the Cayman hospitality industry, notably working at major beach clubs & hotels and devoting herself to the Pink Ladies Charity, Noelle was instantly a major “plus” to our team.

People’s person that she is, her network helped Cayman Villas grow in a way founder Penny Cumber had only dreamt of.

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Our Story

- Words by founder Penny Cumber

The beginning

"A few adventurous and wise snow birds built 2nd homes in a pristine secret paradise hideaway in the 50’s and 60’s called the Cayman Islands. But when they left, they needed home management, so we obliged to look after these lovely villas on the then deserted beaches. One day, Cayman's first Director of Tourism suggested renting them to visitors….. and "hey presto"! The rental business took off!

Starting so early, expertise, long lasting relationships, efficiency, compliance with the law and valuable knowledge gathered over the years. Since then, the company has gone from strength to strength and now warrants the impeccable reputation it deserves."

A love Story

"The reason I’ve loved my business from the start is because it is so much fun! We deal with enthusiastic owners who have invested in our Islands, and excited guests who look forward to a holiday filled with all the delights of a beautiful warm and friendly Caribbean vacation. And "friendly" is the key word, as the people of Cayman are the friendliest, most hospitable, happy people anyone could ever meet… and so very pleasant to do business with!

I‘m also extremely lucky to have such a conveniently located office on the Airport Road, staffed by a team of the most knowledgeable, dedicated, conscientious and efficient ladies who enjoy their days as much as I do! The perfect place to do business and meet and greet our clientele. The mix of this delicious tropical cocktail is just full of fun and happiness. This is not a job, it’s a joy and a privilege to be part of these wonderful and spectacular Islands!"
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 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
The villa surpassed our expectations! It was the perfect property and Cayman Villas were the perfect host! Thank you for the best snorkelling EVER!! Rebecca from the UK.