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 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

Repeat Guests Save More

CaribbeanDays is proud of their ever growing client database. We feel it’s time to thank our clients with a promotion targeted specifically to St Martin repeats guests We are extending a limited time promotion through this low season 2016, offering a 15% discount with a $250 Concierge Credit for the villas outlined below and available exclusively…


St Martin and Barbados Offer 5% Discount

Ready for a vacation to St Martin or Barbados? Reserve your travel dates by May 15, 2016 and received a 5% discount on a villa rental. Not sure where to stay?  Ask us!  We will be happy to find the best vacation home for your stay! Valid on new reservations only.  Valid on travel to…


Anguilla – Upcoming Events

MOON SPLASH, one of the Caribbean’s best and liveliest music festivals.  Kicks off on Anguilla’s beautiful Rendezvous Bay beach from April 21 – 24, 2016. Now in its 26th year, the festival was founded and is still hosted annually by Anguilla’s own Bankie Banx, known as “the Anguillan Bob Dylan,” whose music style combines reggae,…

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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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