Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Save up to 16% by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


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.


Top Hotel Deals

See all 10,085 properties in Caribbean
Hotel El Convento
Hotel El Convento

Hotel El Convento

100 Cristo St, San Juan
     
    4.7
    of 5, from 1,528 reviews
    4.5 out of 5.0

    Located in San Juan Antiguo, this luxury hotel is steps away from Museo del Nino's, San Juan Cathedral and San Juan Gate. La Fortaleza - Palacio de Santa Catalina and Convento de Los Dominicos are also within 5 minutes.

    Hotel Plaza De Armas Old San Juan
    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 1,102 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
      British Colonial Hilton - Nassau

      British Colonial Hilton - Nassau

      Number One Bay St, Nassau
         
        3.9
        of 5, from 1,435 reviews
        4.0 out of 5.0

        Located in Downtown Nassau, this beachfront hotel is in the city centre and within 1 mi (2 km) of New Providence Island and Fort Fincastle. Pompey Museum and Straw Market are also within 5 minutes.

        Sheraton Old San Juan Hotel
        Sheraton Old San Juan Hotel

        Sheraton Old San Juan Hotel

        100 Brumbaugh Street, San Juan
           
          4.0
          of 5, from 2,463 reviews
          4.0 out of 5.0

          Located in San Juan Antiguo, this hotel is steps away from Pier 3, Port of San Juan and Teatro Tapia. Pier 4 and Pier 1 are also within 5 minutes.

          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 663 reviews
            4.5 out of 5.0

            Located in Paradise Island, this beachfront resort is next to a golf course, 0.5 mi (0.7 km) from Cabbage Beach, and within 6 mi (10 km) of Blue Lagoon and Junkanoo Beach. Saunders Beach and Prince George Wharf are also within 6 miles (10 km).

            Boutique Hotel Palacio
            Boutique Hotel Palacio

            Boutique Hotel Palacio

            Calle Duarte 106, Santo Domingo
               
              4.3
              of 5, from 1,143 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
              Comfort Suites Paradise Island

              Comfort Suites Paradise Island

              Paradise Island Drive, Paradise Island
                 
                4.0
                of 5, from 2,232 reviews
                4.0 out of 5.0

                Situated near the beach, this hotel is within a 10-minute walk of Versailles Gardens and Cabbage Beach. Stingray City and Fort Fincastle are also within 3 miles (5 km).

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

                The Royal at Atlantis, Autograph Collection

                Paradise Beach Drive, Paradise Island
                   
                  4.0
                  of 5, from 1,716 reviews
                  4.0 out of 5.0

                  Located in Paradise Island, this beachfront resort is next to a golf course, 0.4 mi (0.7 km) from Cabbage Beach, and within 6 mi (10 km) of Blue Lagoon and Junkanoo Beach. Saunders Beach and Prince George Wharf are also within 6 miles (10 km).

                  Top Flight + Hotel Deals

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.