Caribbean Vacation Rentals


When warm weather and calm waters beckon, pack your bags and head to the Caribbean. A vacation rental at a villa, cottage or residence gives you the freedom and flexibility to discover your island paradise while enjoying the comforts of home. From secluded luxury hideaways to hassle-free family fun, there’s a vacation here for every visitor - and just like the islands of the Caribbean, no two are the same.

Jamaica Coast


Miles and miles of excellent beaches make Jamaica one of the top destinations in the Caribbean. This truly is a place to relax, unwind and take life a little slower for a time.

Surfers at Zuma beach at sunset

Turks & Caicos

These divine Caribbean islands offer miles of magnificent white-sand beaches, turquoise waters, kitesurfing and a bounty of incredible dive spots.

Turks & Caicos


Just a short flight from Miami, the Bahamas is the perfect choice for a relaxed island getaway. Here, you'll find an ideal mix of pristine beaches and lively entertainment.

St Lucia Piton

Saint Lucia

Saint Lucia delights your spirit of adventure with the world's only drive-through volcano, mud baths, and lush rainforest hikes.

Dominican Republic beach

Dominican Republic

Countless activities and eco-adventures await! Indulge in world-class golf and fishing, or explore the magical underwater world of coral reefs, caves and shipwrecks.

Paddle Boarder, US Virgin Islands

U.S. Virgin Islands

Enjoy glistening beaches and duty-free shopping with no passport required in the U.S. Virgin Islands

Cayman Islands

Cayman Islands

Explore more than 200 dive sites teeming with marine life, encounter majestic stingrays and discover the islands' enchanting people and traditions.



Think Bermuda and images of tidy pastel cottages, pink-sand beaches, and quintessential British traditions like cricket matches and afternoon tea spring to mind.

Puerto Rico

Puerto Rico

The intriguing Caribbean island and U.S. territory of Puerto Rico offers diverse vacation experiences to thrill every sort of traveler.

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]