Your Caribbean Getaway Starts Here

How We Are Different?
We're Experts on the Region

We have been frequent visitors to the Caribbean for the past twenty-five plus years, often spending a week out of each month in the region. We can answer any question you may have about the islands and about the luxury Caribbean villas. If we don’t know, we find out.




At Your Service

CaribbeanDays provides the highest level of personal assistance in order to ensure that all of your vacation needs are met. Our team of dedicated Caribbean travel agents will help you find the perfect Luxury Caribbean Villas for you.


Quality Rentals

Our descriptions of the Caribbean vacation villas are always true and accurate. A large percentage of our business consists of repeat and referral clientele and we strive to keep it that way. Let us help you find a luxury Caribbean villa for the vacation of your dreams.


Explore the Caribbean
Explore All Of Our Caribbean Destinations
We Are Here For You

We represent over 1000 luxury Caribbean villa rentals on more than 20 island throughout the Caribbean. Let CaribbeanDays ensure your Caribbean Holiday exceeds your expectations from arrival to departure.

When you phone us you will be able to speak with someone who is very knowledgeable about the Caribbean villa rentals and the islands, and you will never have to deal with a telephone menu.

Get to know our team
CaribbeanDays Blog

Fun Disney Tidbit

CaribbeanDays can book your stay so you can go to Hollywood Studios! At Hollywood Studios, in the Muppet 3D room of Muppet Vision, there is a display hanging from the ceiling of “a net, full of Jell-O”. This is a play on words to symbolize Annette Funicello! BTW, this was actually the Beach Boys debute!


A Unique Experience Awaits You in the Cayman Islands!

One of the most unique experiences the Caribbean Islands offers to guests are stingray encounters. The stingrays gather in two places. One is Stingray City and also The Sandbar of the North Sound in the Cayman Islands. Years ago, fishermen would drop anchor in these shallows of the North Sound to clean their fish. The…


New Regulation with Drone Use for Caribbean Islands

The Caribbean Islands have a new regulation in place for the use of drones by guests on their stay. Guests can still use them. They do. They have shared great footage with drones. But due to safety measures, a few new steps have been put in place for bringing drones on your stay. CaribbeanDays is…

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Contact a Villa Specialist

Not sure where to start your search for a Caribbean villa rental?

Contact a CaribbeanDays villa specialist today! Having visited each and every Caribbean island many times, our specialist can guide you in choosing the right island and villa for your getaway. Fill out the form below to contact a specialist and get started.

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