Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Book the Best Caribbean Vacations (Flight + hotel)

Choose one or more items to build your trip:

Caribbean Vacation: Coronavirus Information

Most Caribbean hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Caribbean trip, please visit our Coronavirus Information page (opens in new window).

Top Caribbean Flight + Hotel Deals

Weston Suites & Hotel
The Cove at Atlantis
Emotions by Hodelpa - Juan Dolio
Caprice 7 Ocean Front Villa private Pool
Casas del XVI

Top Hotels in Caribbean

Hotel El Convento
Hotel El Convento
4.5 out of 5
100 Cristo St, San Juan
Free CancellationReserve now, pay when you stay
The price is $189 per night from Jun 1 to Jun 1
4.6/5Exceptional! (972 reviews)
"Loved the old school feeling of being in old San Juan. The entire hotel was kept especially clean. The staff was friendly and efficient. The only thing I did not like was they say it is a queen sized bed but more on the full size side. I’m a tall guy my feet were never on the bed. Aside from that ..."

Reviewed on May 7, 2021

Hotel El Convento
British Colonial Hilton - Nassau
British Colonial Hilton - Nassau
4 out of 5
Number One Bay St, Nassau
Free CancellationReserve now, pay when you stay
The price is $240 per night from May 11 to May 11
3.8/5Good! (994 reviews)
"Hilton is doing the best during these unfortunate and ridiculous times"

Reviewed on Apr 24, 2021

British Colonial Hilton - Nassau
Sheraton Old San Juan Hotel
Sheraton Old San Juan Hotel
4 out of 5
100 Brumbaugh Street, San Juan
Free CancellationReserve now, pay when you stay
The price is $169 per night from Jun 1 to Jun 1
4.1/5Very Good! (1,005 reviews)
"The place was very clean and was close to everything which was very convenient. But we paid for a room with balcony and ocean view got there the room had a very small window that was our ocean view and it was very disappointing that they charge you for balcony knowing the hotel has no balcony. Other ..."

Reviewed on May 9, 2021

Sheraton Old San Juan Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Caribbean Vacation Packages

Have a warm island vacation at any time of year on your choice of lush tropical islands. The Caribbean islands offer an amazing choice of beaches for tropical 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 during the best Caribbean vacations.

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