About Us

A trusted leader in the luxury Caribbean house rentals industry, CaribbeanDays has offered its guests the finest Caribbean villa rentals for more than 40 years. We offer more than your typical Caribbean Travel Agency. We are here to help you every step of the way in planning your dream Caribbean vacation – from house or villa rentals to finding the best places to dine, explore, and more.

We represent over 1,000 luxury Caribbean villa rentals on more than twenty islands throughout the Caribbean. Our Caribbean travel agency provides the highest level of personal assistance in order to ensure that all of our Caribbean house rentals exceed expectations. Let CaribbeanDays offer you that same level of personal service on your next Caribbean vacation.

We have been frequent visitors to the Caribbean for the past forty plus years, often spending a week out of each month in the region. 

A large percentage of our business consists of repeat and referral clientele and we strive to keep it that way.

We believe our passion to excel and provide unsurpassed personal service has enabled our continued growth and success in the Caribbean house rentals market.



Back in 1978 a woman took a trip to the island of St. Martin/St. Maarten.  She fell in love with the island and purchased a vacation home on the Dutch side.  She began renting it and found that she could earn an income from these rentals.  Having wonderful taste for design, she tastefully decorated her home and found it hard to keep the villa open for her own personal use. She purchased another, and another and found that she could make this a real business for herself.  Her name is Maria and she is my mother.  I was 12 years old when she first went to St. Maarten.  I had a childhood of visiting the Caribbean a few times a year…not so bad…I quickly had a lot of friends.

Maria started to expand her rental business over the years to other Caribbean islands and eventually I got to visit them all.  I am able to carry on a wonderful business that my sweet mother left me in her passing on Sept. 11, 2013, her 65th birthday.

Let’s Enjoy the travel


CaribbeanDays is proud to work with some of the finest companies in the travel industry which allows us to bring you the best possible Caribbean vacation getaway. We offer our customers best-of-breed travel related products and services as a value added means to further enhance all villa vacations that we help to plan.


We believe our passion to excel and provide unsurpassed personal service has enabled our continued growth and success in the Caribbean house rentals market.


CaribbeanDays is committed to offering its guests the finest travel resources available. With access to real-time Caribbean weather updates, interactive Caribbean maps or our exclusive Villa Guide, CaribbeanDays provides the information that will ensure your Caribbean vacation is as enjoyable and stress-free as possible. Add our extensive list of travel partners and CaribbeanDays’ fabulous villa specialists and guest service coordinators and you have, quite simply, the finest vacation planning experience money can buy.


Why are there so many different rates for the same house during that same time of year?

Villa rental rates are based on the number of bedrooms used.  2 persons per bedroom are allowed unless a child is 2 years old or younger or special permission is granter ahead of time.  If you show up for your arrival with more people than you have paid for you will have be asked to pay the difference or you may not be permitted access to your rental property.

Can I request a late check out or early check in?

You may request a late check out or early check in, however you will not have a final answer, most likely until a week before you arrive.  The villa owners will not grant permission just in case they can get a last minute reservation.  There are times that permission may be granted ahead of time and a fee will be added.  It is best to question your rental agent regarding this so plans can be put into place for your arrival/checkout.

Can arrangements be made for car rentals, chefs, massages, villa provisioning, etc.?

CaribbeanDays can make arrangements for anything you would like prior to your arrival.  If you are unsure and decide at the last minute we will do our best to have it arranged for your arrival.  You will be given an emergency contact phone number while on island so you will have access to someone at all times.

How do we get from the airport/ferry dock to our villa/condo?

Once your final payment is made you will be given your arrival instructions.  Please read them carefully and contact our office should you have any questions.  You will be given important contact phone numbers and arrival details in these instructions that you need to bring with you in case of a flight delay or cancellation.  If you do not show up for your arranged greeting or on your predetermined flight/ferry, and you have not notified your greeter, you may be charged a fee to set up another greeting.  Arrival instructions differ per island and even per rental property as do emergency contact numbers.  If you have traveled to a specific location or villa in the past please don’t assume that the contact info or arrival details are the same as they were previously.

Payments and Cancellations, how does this work?

Initial deposits are due within 4 days of receiving your rental agreement and depending on the time of year traveling, the final payment is due 75 – 120 days prior to your arrival on island.  If you are making your reservation less than 75 days from your departure, your full payment will be due at that time.

CaribbeanDays strongly recommends that you purchase trip cancellation insurance.  We do have a partnership with Travel Guard if you follow the link from our homepage,  for your convenience.  Whether you use Travel Guard or another company, it is important that you protect your hard earned vacation as the cancellation policies are very strict.

Do I need to bring beach and bath towels and bed sheets?

No.  All of our rental properties will be equipped with all linens, bath and beach towels.  If you are uncertain about an amenity or you do not see it listed on our website, please email or call us and we will confirm whether your rental property is equipped with that item or not.  It is best to find out ahead of time so you are not expecting something that is not there or you pack something you did not need.

Let us do all the searching for the most ideal Caribbean vacation.