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.

Caribbean Vacations

Choose two or more items to start building your trip:

Top Holiday Package Deals in Caribbean

Sheraton Santo Domingo Hotel
Sheraton Santo Domingo Hotel
4 out of 5
Gascue
$704
$567
per personAug 27 - Aug 31
Roundtrip flight included
New York (JFK) to Santo Domingo (SDQ)
4.4/5Excellent! (891 reviews)

"I like the cleanliness and the amenedies t For your guest Didn’t like that i got charge for an early check in when the room was available…"

Reviewed on Mar 22, 2020

British Colonial Hilton - Nassau
British Colonial Hilton - Nassau
4 out of 5
Downtown Nassau
$917
$739
per personAug 18 - Aug 23
Roundtrip non-stop flight included
Newark (EWR) to Nassau (NAS)
3.8/5Good! (1,687 reviews)

"I didn't like the swimming pool schedule -9 to 5- leave that for an office, but not for a hotel. THey only gave a couple of bottle of water at the check in, and none afterwards…"

Reviewed on Mar 14, 2020

Casas del XVI
Casas del XVI
5 out of 5
Ciudad Nueva
$1,173
$1,033
per personAug 27 - Aug 31
Roundtrip flight included
New York (JFK) to Santo Domingo (SDQ)
4.6/5Wonderful! (64 reviews)

"Amazing! The photos on Expedia do not do this hotel justice. The houses are historic, and beautiful in every way. Rooms are very clean and staff were super helpful. There is always a security guard on the street corners, and your butler is available 247. I recommend!…"

Reviewed on Mar 24, 2020

Renaissance Santo Domingo Jaragua Hotel & Casino
Renaissance Santo Domingo Jaragua Hotel & Casino
4.5 out of 5
Gascue
$761
$678
per personAug 27 - Aug 31
Roundtrip flight included
New York (JFK) to Santo Domingo (SDQ)
4.4/5Excellent! (650 reviews)

"The property is well kept in all aspect considering the pandemic situation. The best part was the staft that handle this situation and made our stay presurable, thanks Adon, Jose, Ramon and the young front desk lady that lend us the umbrella. Thank you all.…"

Reviewed on Mar 30, 2020

El Greco Hotel
El Greco Hotel
2.5 out of 5
Downtown Nassau
$590
$529
per personAug 18 - Aug 23
Roundtrip non-stop flight included
Newark (EWR) to Nassau (NAS)
2.9/5 (347 reviews)

"the staff were helpful and friendly. clean rooms. well worth the affordable price.…"

Reviewed on Jul 1, 2020

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Top Hotels in Caribbean

Estimated price for 1 night / 2 adults
Hotel El Convento
Hotel El Convento
4.5 out of 5
100 Cristo St, San Juan
4.7/5Exceptional! (1,000 reviews)

"Beautiful hotel in the heart of Old San Juan. Walking distance to everything - classic feel with charming features including central courtyard."…"

Reviewed on Apr 24, 2020

Hotel El Convento
Hotel Plaza De Armas Old San Juan
Hotel Plaza De Armas Old San Juan
2 out of 5
Viejo San Juan, San Jose St, 202, Btw San Francisco St and Fortaleza, San Juan
3.6/5Good! (1,000 reviews)

"This was a very old hotel in Old San Juan. We spent one night there before our cruise. It was exactly what we were looking for. While it was old, it was clean and the staff was very accommodating. It was right in the heart of Old San Juan within walking distance of everything we wanted to see and ..."…"

Reviewed on Feb 23, 2020

Hotel Plaza De Armas Old San Juan
British Colonial Hilton - Nassau
British Colonial Hilton - Nassau
4 out of 5
Number One Bay St, Nassau, New Providence
Free CancellationReserve now, pay when you stay
The price is $195 per night
3.8/5Good! (1,687 reviews)

"I didn't like the swimming pool schedule -9 to 5- leave that for an office, but not for a hotel. THey only gave a couple of bottle of water at the check in, and none afterwards"…"

Reviewed on Mar 14, 2020

British Colonial Hilton - Nassau

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.

Frequently asked questions

Q: What are the most popular types of hotels for a vacation to Caribbean?
A: You’re spoiled for choice when it comes to accommodations in Caribbean. The most popular places are guest houses. But if that doesn’t suit, you can also pick from apartments, villas, hotels and much, much more.
Q: What does a Caribbean vacation booking with Expedia include?
A: It all comes down to what kind of getaway in Caribbean you want. You can pick a hotel and flight, or car, flight and hotel, or hotel and car — or any of these individually. If you like, you can also throw in some attractions and experiences.
Q: What is the best way to save money on my vacation to Caribbean?
A: A package deal makes traveling easier, and it can save you a pretty penny as well. Hotels, Flights, Experiences, Rental Cars — Expedia can help. Bundle them up and start dreaming about what you’re going to do with that extra spending money.