In the Cayman Islands, Dreams do come true

About Cayman Vacations

Who are we and what do we offer?

Info from 25+ web sites, all right here!

CaymanVacations is the largest Cayman Islands vacation rental web site.
We offer 500+ rental condos & private villas in the Cayman Islands.

  • Online since 1999
  • Largest Cayman Reservation Site
  • Endorsed by Cayman Tourism
  • 500+ Rental Condos & Villas
  • 30+ Full Condo Resorts
  • 3 Property Management Companies
  • Info from 25+ Web Sites
  • Accurate Rates
  • Current Specials
  • Area Maps and Information
  • Resort Photos
  • Detailed Resort Info
  • Detailed Unit Info
  • Directory of Condo Units
  • Easily Compare Options
  • REAL TIME Availability
  • REAL TIME Reservations
  • NO Booking Fees!
  • Secure & Reliable
  • Trusted & Respected
  • Unbiased Opinions
  • We're Here to Help YOU
  • Problem Solving
  • Find Everything you need!
  • Need we say more?


We offer the rental units from over 25 condo resort offices, as well as individual condo units and 25+ private villas from 2 property management/reservation companies. Our web site essentially consolidates all the information from all of these other web sites all in one place - we have it all, so there is really no need to check elsewhere! is a Caribbean Travel Group Ltd company (CTG) and is based in the Cayman Islands. We have operated online since January of 1999. We are endorsed by the Cayman Islands Department of Tourism (DOT) and the Cayman Islands Tourism Association (CITA) – the 2 main tourism organisations in the Cayman Islands.

We're Here to Help You

We're there to help solve any disputes or problems you may have with the condo resort. It's rare there are problems, but it's nice to have help on the rare occasion when a problem arises. Our staff have all lived in the Cayman Islands for years, so we know the beach, the areas and each resort! We'll give you an unbiased opinion on each resort too. We want to help you find the best resort for YOUR preferences, budget, etc. Everyone's tastes are different, and we realize that. It doesn't matter to us if you book resort a, b, c or d... we just want to book you the condo that suits your requirements best!

Why should I book through this web site?

The choice is yours, but there are many reasons to use our service. It is quick, efficient, unbiased, free to use, and just the best way to check as many options as possible in the shortest possible time. With our combination of web sites: showing all condo resorts, and showing exact availability for all automated condo resorts - you won’t find a more complete overview of the various options anywhere else. Make sure you have all the info and choose the best available option for your dates. Save a ton of time and money as you no longer have to find and then check multiple web sites or call or email 5 or even 10 or more different properties to check availability and find out what prices are. You can see it all on and and have a confirmed reservation in a fraction of the time!!

Furthermore, in our automated site, as the name suggests, you are actually booking DIRECT with each resort when you use Our booking system is tied directly into each resort office’s computer, so they receive your reservation instantly, process the payments, issue refunds etc. CayDirect is just a conduit to help you find and book any one of many condo resorts or villas – all in one place. VERY Convenient!

Real Time Reservations

More than half of all properties now offer automated reservations... is our NEW automated booking web site, and is the result of a collaboration between CTG, DOT and CITA and was created in order to provide a single central reservation system offering LIVE or REAL TIME availability and reservation capabilities for all automated Cayman Islands condo resorts and villas.

Our 2 web sites are linked and work seemlessly together to provide potential visitors to the Cayman Islands with a one-stop solution where they can check exact availability, compare the rates and facilities of the various condo resorts and villas, and to easily find the best available accommodation for their stay. Our real time booking engine allows the visitor to accurately check exact availability and to reserve any one of hundreds of automated condos or villas in real time – thus eliminating the need for the visitor to check multiple web sites and/or to make multiple phone calls. This is convenient and a huge time saver for the visitor.

All of our properties - even those that do not have automated capabilities and who cannot therefore participate in our automated booking site - are listed on with full detailed information, making it a simple matter for visitors to compare ALL possible options.

How the Booking Engine Works:

Our booking engine allows us to pull availability in “real time” directly from each resort’s own office computer, thus allowing accurate “live” availability. The customer’s search results are displayed in an easy to understand tabbed interface, giving them an overview of the available choices for their dates and criteria. Customers can browse the photos, descriptions and rates of the available resorts and make an informed decision about where they would like to stay. Once a suitable resort is found, the customer can choose the specific condo unit that they would like (where applicable) and reserve it instantly.

Our DIRECT connection to each resort ensures accurate up to date availability and instant confirmation. No more guessing about availability and there is no need to call the resort to verify if it is available or not – the availability is taken directly from the resort office computer, so it is the exact same availability as if you contact the resort directly.

Search for and find the best condo or villa based on your budget and other requirements, book it, and receive a confirmation – instantly!!