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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 350,000 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 local 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 will plan and arrange a vacation for our guests, that goes far beyond the cliché activities. From sun-drenched afternoon adventures to nights out on the town, our guests will experience a truly unforgettable Cayman experience!
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Highly qualified local travel and concierge specialists

Our local 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 home, villa, cottage or condo to match your preferences, budget and great expectations!
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Quality, quantity, limitless possibilities

Choose from the Cayman Islands’ most sought-after beachfront properties. We offer a diverse selection of nightly rates, an array of amenities, locations, styles and sizes. No matter your choice, peace of mind, comfort and unforgettable memories are guaranteed!

Our Team

Meet Cayman Villas' superior and knowledgeable vacation rental management team

Penny Cumber

Retired
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Penny Cumber


Untamed traveller, dream chaser, mother and devoted grandmother, Penny Cumber has spent more than 45 years taking care of visitors, while supporting and building her well-established other passion, Cayman Villas. She started the business from her home in 1970, with just two properties! The business has grown substantially, each year, into a world renowned business providing first class service to our property owners, our visitors and guests and our worldwide business colleagues.

Penny has served on the Cayman Islands Tourism Board, has had a close working relationship with the Department of Tourism for over 4 decades, and is a dedicated Ambassador for the Cayman Islands and all that these amazing islands have to offer our visitors. In October 2017, after almost 47 years in the business, Penny has finally decided to take her very well deserved retirement, and has handed the reigns over to her daughter, Juliet Cumber-Forget.

Penny will always be a significant part of Cayman Villas, and will always remain a Consultant and Booking Agent ‘Guru’ to everyone on the Cayman Villas Team! However, she has a desire to travel and visit her many friends and family around the world, so she now spends 6 months of the year travelling and 6 months here in Grand Cayman. If you are lucky, you may catch her devotedly walking the beach every day, playing with one or all of her 6 grandchildren, or joining in a competitive game of tennis!

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Juliet Cumber-Forget

Business Manager
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Juliet Cumber-Forget


Juliet Cumber-Forget was born and raised in Grand Cayman, and her family have been involved in the tourism industry since the 1960’s! Juliet has grown up working in many areas of the sector from car rentals, watersports, restaurants, Inter-Island Airlines, and of course the accommodations sector with Cayman Villas! From the young age of 12, Juliet has worked at Cayman Villas, and has voraciously learned the business from the ground up. With her mother, Penny, as her mentor and guide, she has just as much passion for Cayman Villas, and the Tourism Industry, so she was the perfect person to take over the business! With over 25+ years working in the tourism industry, Juliet is experienced and knowledgeable, a true professional, and extremely friendly and easy going. She is very familiar with the business and is dedicated to providing her Property Owners and Guests with the best possible service and experience.

When she is not working, she loves spending time with her 3 children, her family and her friends.

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Jennie Cairns

Travel & Concierge Specialist
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Jennie Cairns


Originating from a colder climate Jennie moved to Grand Cayman in 2006 and brings 20 years of hospitality and travel industry experience to Cayman Villas.

Her past experience includes both leisure travel, concierge and trip planning. Her passion and love for travel is seen through her dedication to helping people fulfil their dreams of exploring new cultures through amazing travel experiences.

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Noelle Kelly

Travel & Concierge Specialist
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Noelle Kelly


Originally from Ireland, Noelle came to the Cayman Islands in 1990 to work for a winter season at The Hyatt Regency Hotel, and never left! Almost 28 years later, she has obtained her Caymanian Status and has firmly planted roots in Grand Cayman and now has a family of her own.

With over 25 years of experience in the hospitality industry, notably working at major beach resorts & hotels, and restaurants, Noelle has a wealth of knowledge and information about the islands. She is an avid volunteer and helps as many charitable organizations as she can, with The Pink Ladies as her pride and joy! Noelle knows the islands incredibly well and is an ambassador of the Cayman Islands. Her friendly, outgoing personality is why she is so well liked by all that meet her, including our owners and guests. She is an asset to the Cayman Villas team and is our Reservation and Concierge Specialist.

When she is not working, she spends time with her son, her friends, and she does almost every charity fundraising walk that comes along throughout the year!

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Daisy Anglin

Property Manager, Regal Beach Club, 7MB.
 

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 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.
Thank you for your help in making our honeymoon memorable - from the booking to the champagne. We appreciate your professionalism and personal touch.
John & Anneliese
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.