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Caribbean Vacation Packages

Have a warm beach vacation at any time of year on your choice of lush tropical islands. Snorkel, dive, sail or simply relax and enjoy laid-back island life.

The Caribbean islands offer an amazing choice of beach vacations, high-end shopping and fascinating cultures. Stop in major ports on a luxury cruise or charter a sailboat to hop from one to another of thousands of islands. Sunbathe on vast sandy shores. Scuba and snorkel in clear waters filled with colorful fish. 

Beautiful beaches are common across the region, while art, architecture, cuisine and customs vary from island to island. Appreciate the pleasing mix of cultures of the indigenous island people and descendants of European settlers. 

Aruba, Bonaire and Curaçao off the coast of Venezuela display Dutch influence. Have rijstaffel, a Dutch colonial meal of rice accompanied by 20 to 30 side dishes. Aruba has an unusually dry terrain, with miles of sandy beaches on the northwestern shores. Look for divi divi trees blown to the side in the region’s strong winds. Bonaire’s marine park and donkey sanctuary feature a range of wildlife. On Curacao, swim with dolphins and participate in extreme sports. 

See the colorful buildings in old San Juan and the castles across the U.S. territory of Puerto Rico. St. Thomas of the U.S. Virgin Islands is a popular tour boat stop for buying diamonds and lazing on beaches. Nearby St. John is dominated by the Virgin Islands National Park, on land and in the underwater reefs. Learn about the 2,000 years of human occupants, including native Caribs, in the Salt River Bay National Historical Park on St. Croix.

For many people, Cuba has for decades been a land of mystery under Communist rule. While U.S. residents are not allowed to visit strictly for tourism, licensed visits can be arranged for various purposes. While here, see the cathedrals, squares and museums of Old Havana and visit exceptional beaches.

View the tropical plants in Hunte’s Gardens on Barbados. Dive and sample rum at a distillery on the Cayman Islands. Observe waterfalls and wildlife in the Dominican Republic. On the western side of the island, explore the Citadelle of Haiti. Golf, ride a bobsled and listen to steel drum music on Jamaica. Learn about Christopher Columbus and the native Arawaks while visiting the more than 700 islands of the Bahamas

Most important of all, enjoy beach after beach after beach in the Caribbean region.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 13,950 Properties in Caribbean
Hotel El Convento $187
Hotel El Convento

Hotel El Convento

100 Cristo St, San Juan
     
    4.7
    of 5, from 1,564 reviews
    4.5 out of 5.0

    Formerly a convent dating from 1651, this boutique hotel is in the center of Old San Juan across from the San Juan Cathedral and two blocks from La Fortaleza, now the governor's mansion.

    Hotel Plaza De Armas Old San Juan $80
    Hotel Plaza De Armas Old San Juan

    Hotel Plaza De Armas Old San Juan

    Viejo San Juan, San Jose St, 202, San Juan
       
      3.5
      of 5, from 1,105 reviews
      2.0 out of 5.0

      Located in San Juan Antiguo, this hotel is within a 10-minute walk of Museo del Nino's, Plaza de Armas, and Museum of the Americas. Museo de Casa Blanca is 0.3 mi (0.5 km) away.

      British Colonial Hilton - Nassau $162
      British Colonial Hilton - Nassau

      British Colonial Hilton - Nassau

      Number One Bay St, Nassau
         
        3.9
        of 5, from 1,469 reviews
        4.0 out of 5.0

        Serving as the island's social and business hub, the 288-room beachfront hotel is across from the Straw Market and 5 blocks from Parliament Square. A seaside dining village known as Arawak Cay Fish Fry is 500 yards (457 meters) west of the hotel.

        Sheraton Old San Juan Hotel $152
        Sheraton Old San Juan Hotel

        Sheraton Old San Juan Hotel

        100 Brumbaugh Street, San Juan
           
          4.1
          of 5, from 2,488 reviews
          4.0 out of 5.0

          Located along the water in Old San Juan, this contemporary Puerto Rico resort is across from cruise-ship piers and 3 blocks from the massive Fort San Cristóbal.

          The Reef at Atlantis, Autograph Collection
          The Reef at Atlantis, Autograph Collection

          The Reef at Atlantis, Autograph Collection

          Paradise Beach Drive, Paradise Island
             
            4.4
            of 5, from 734 reviews
            4.5 out of 5.0

            The Reef at Atlantis, Autograph Collection, located directly on a white-sand beach, is close to numerous attractions including Atlantis Aquarium, Cabbage Beach, and Aquaventure. Fort Fincastle and Prince George Wharf are nearby.

            Boutique Hotel Palacio $77
            Boutique Hotel Palacio

            Boutique Hotel Palacio

            Calle Duarte 106, Santo Domingo
               
              4.3
              of 5, from 1,201 reviews
              3.5 out of 5.0

              Located in Colonial Zone, this hotel is within a 5-minute walk of Calle Las Damas and Parque Colon. Cathedral of Santo Domingo and Alcazar de Colon are also within 10 minutes.

              Comfort Suites Paradise Island $251
              Comfort Suites Paradise Island

              Comfort Suites Paradise Island

              Paradise Island Drive, Paradise Island
                 
                4.0
                of 5, from 2,265 reviews
                4.0 out of 5.0

                This casual, all-junior suite property provides guests access to Atlantis and full use of their resort facilities just one block away, and two golf courses are a mile away.

                The Royal at Atlantis, Autograph Collection
                The Royal at Atlantis, Autograph Collection

                The Royal at Atlantis, Autograph Collection

                Paradise Beach Drive, Paradise Island
                   
                  4.1
                  of 5, from 1,817 reviews
                  4.0 out of 5.0

                  These spire-topped towers contain 1,201 rooms and embody the Lost Continent theme offered by the water-park and marine-life Atlantis resort on Paradise Island, which connects by bridge to Nassau.

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