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Caribbean Travel and Vacation Rentals Info

When the winter blues hit, there is one quick solution: book a trip to the Caribbean. No matter what island you pick, you will be miles away from piles of snow and instead will be sipping on a frozen cocktail while watching the sun set. That being said, there are many different experiences throughout the Caribbean. It pays to do your research and pick an island based on your preferences. The couple looking for a romantic retreat will pick a different destination than the family looking for a range of activities. If you’re new to this area, keep reading for an overview of Caribbean travel and vacation rentals info.

When to Visit

Weather can vary depending on what island in the Caribbean you choose to visit, but there are some general rules too. Late August and September are considered prime hurricane season in the Caribbean, so many travelers avoid this period (or book a last minute trip when the coast is clear). If you’re concerned about crowds, avoid traveling to the Caribbean over the holidays in December and during school breaks.

The best weather in the Caribbean is experienced from December through April. During these months the weather is generally dry and sunny. This period also corresponds with winter in the northern hemisphere, making it doubly attractive. These months are considered high season and prices will be higher accordingly.

The low season in the Caribbean is from May through November. If you’re trying to plan a trip to the Caribbean on a budget, May and June are great times to go. Kids are still in school and you won’t be in danger of hurricanes during these months. Remember, before booking a trip to any Caribbean island — whether it’s the Bahamas, Dominican Republic, or Aruba — to check for fluctuations in the weather (such as rainy periods or months of extreme humidity).

What to Expect

The Caribbean is beloved by so many travelers because it is easy, relaxing, and beautiful. Airfare is often affordable and direct flights are on offer. Each island has miles of sugary beaches that are perfect for sunbathing, swimming, and snorkeling. In addition, on many islands the main language is English and American dollars are the main currency. This makes international travel in the Caribbean a breeze.

Travelers should expect different things from each island. All the islands of the Caribbean have their own flavor and reputation. Aruba has excellent restaurants and casinos. The Bahamas is known for snorkeling and family entertainment. The Cayman Islands has some of the best scuba diving in the Caribbean and offers excellent horseback riding tours on the beach. From Puerto Rico to Anguilla, the Caribbean is full of palm-fringed beaches and delicious seafood specialties.

A trip to the Caribbean can be as active or relaxing as you please. Adventurous travelers can fill their days with deep-sea fishing expeditions, zip line tours, rounds of golf, and surfing classes. If you would rather relax, there are sunset sails, dolphin watching tours, and beach shacks with rum-based cocktails. Expect beautiful scenery, friendly people, and a relaxed way of life throughout the Caribbean.

Must Bring

Another reason travelers are so infatuated with the Caribbean is that packing is a cinch. Throw a bathing suit and a pair of flip flops in a bag and you will be just about ready to go. With sunscreen, a couple books for the beach, and a sundress for evening meals, you will be set to go to enjoy a week in the Caribbean. In addition to your beach basics, some travelers like to bring entertainment for the vacation rental like favorite DVDs or a deck of cards.

Each island has its own character, so be sure to investigate further once you choose a destination. For example, with Aruba’s casino and nightlife scene, you might want to bring some dressier outfits for the evening. The nightlife scene in Jamaica is casual and won’t require anything too fancy. Some of the islands offer activities like hiking and biking. If you plan on participating, you might also want to bring a pair of hiking boots.

Getting There

The Caribbean remains a popular choice for travelers year after year because it is so easy to reach. Some travelers who aren’t too picky about their destination choose an island based on affordable airfare. Islands with some of the biggest airports and airports with the best airfare include the Bahamas, Jamaica, the Dominican Republic, and Puerto Rico. Many airlines offer seasonal service to destinations in the Caribbean during the winter months. This service is often direct and especially convenient for travelers that don’t have much vacation time.

For additional travel information visit our Caribbean video guide page.

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Vacation Rentals in Caribbean (28,493)

  • 1 - 50 of 28,493
Additional fees apply. Taxes may be added.
    • 3 BR
    • 3 BA
    • 1 HF BA
    • Sleeps 6
    Condo #962090vb
      • 2 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 5
      Condo #931019vb
        • 2 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 5
        Condo #932854vb
          • 1 BR
          • 1 BA
          • Sleeps 4
          Cottage #450824vb
            • 2 BR
            • 2 BA
            • Sleeps 5
            Villa #947779vb
              • 1 BR
              • 1 BA
              • Sleeps 4
              Condo #922436
                • 1 BR
                • 2 BA
                • Sleeps 4
                Apartment #6563195
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Cottage #916895vb
                    • 2 BR
                    • 1 BA
                    • 2 HF BA
                    • Sleeps 4
                    Bungalow #509036vb
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                      Apartment #755419vb
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Studio #472640vb
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          Cottage #3896752
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Villa #145641
                              • 2 BR
                              • 2 BA
                              • Sleeps 8
                              Condo #4222585
                                • 1 BR
                                • 1 BA
                                • Sleeps 5
                                Condo #115285vb
                                  • 1 BR
                                  • 2 BA
                                  • Sleeps 3
                                  Townhome #802716vb
                                    • Studio
                                    • 1 BA
                                    • Sleeps 6
                                    Studio #4274079
                                      • 3 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Apartment #3944819
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 2
                                        Apartment #4129987
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 3
                                          Cottage #3489783
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Condo #3871493
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #320285vb
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                Cottage #432968vb
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #4303755
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Cottage #412659vb
                                                      • 1 BR
                                                      • 1 BA
                                                      • 1 HF BA
                                                      • Sleeps 4
                                                      Apartment #1482106a
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        Villa #628184vb
                                                          • Studio
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Studio #913469a
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Villa #4294692
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 3
                                                              Apartment #986220
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 3
                                                                Condo #899469vb
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Villa #1478106a
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 10
                                                                    Villa #3918855
                                                                      • Studio
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Studio #4210869
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Bungalow #1482070a
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Villa #506303vb
                                                                            • 1 BR
                                                                            • Sleeps 2
                                                                            House #1387978a
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              Cottage #595203vb
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 4
                                                                                Apartment #610527vb
                                                                                  • 2 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 5
                                                                                  Villa #4267511
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Apartment #591784vb
                                                                                      • 5 BR
                                                                                      • 4 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 10
                                                                                      House #756299vb
                                                                                        • Studio
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Studio #814176vb
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Condo #245798vb
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Condo #836298
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              Villa #6842649
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                Townhome #569057vb
                                                                                                • 1 - 50 of 28,493