Caribbean Vacation Rentals, Villas, & More

7,276 Caribbean rentals

More Caribbean Vacation Rentals

About Caribbean

With hundreds of destinations, each with its own unique attractions and personality, there’s a Caribbean island to suit every traveler. Book the Caribbean vacation rentals of your choice for a relaxing, adventurous, or romantic stay in the islands.

Caribbean Climate

From Cuba on the west to Trinidad in the east, the 700 islands in the Caribbean enjoy an oceanic tropical climate. Temperatures and rainy seasons vary slightly from island to island, but in general, all islands tend to be hot and humid. Summer temperatures generally reach the upper 80s or low 90s, while winter temperatures hover in the low 80s. Since the Caribbean’s rainy season and hurricane season span from June through November, many travelers prefer to visit during the winter and spring.

How to Get Around the Caribbean

To visit multiple Caribbean islands during a short period of time, it’s best to book a cruise that stops at some of your preferred islands. To plan a longer stay on one or two islands, however, fly to the island of your choice and take advantage of island public transit. On most islands, you can hop from Caribbean vacation rentals to beaches and back using a combination of taxis, minibuses, and motorbikes.

Things to Do in the Caribbean

The Dominican Republic is best known for its beaches and charming historic quarters, so start your day here with a walk along Playa Rincón and a dip in the sea. If you’re looking for something even more remote, charter a boat to Bahía de Las Águilas, one of the island’s most secluded beaches. Don’t forget to visit the colonial district in Santo Domingo, which is the New World’s oldest city. Here you can walk along 16th-century streets and peek at historic mansions.

A handful of nations make up the U.S. Virgin Islands, and most of the action happens on St. Thomas, St. John, and St. Croix. Go for a picturesque swim at Magens Bay, one of the most popular beaches on St. Thomas and throughout the U.S. Virgin Islands. On St. John, hike, boat, and swim through the 7,000 acres of Virgin Islands National Park. On St. Croix, discover the island’s boozy history at the Cruzan Rum Distillery and learn about its centuries of sugar cane production at the Estate Whim Plantation Museum.

When you visit Aruba, you won’t want to miss Eagle Beach or Hadicurari Beach, two of the best spots on the northwestern edge of the island. Scope out the windsurfers and ...

Read more