Book the Best Caribbean Vacations (Flight + hotel)
Top destinations in Caribbean
Kingston
Jan 18 - Jan 22
from $516
flight + hotel per person
Montego Bay
Feb 10 - Feb 14
from $575
flight + hotel per person
Santo Domingo
Feb 10 - Feb 14
from $433
flight + hotel per person
St. John
Jan 31 - Feb 3
from $951
flight + hotel per person
Nassau
Jan 25 - Jan 29
from $1,139
flight + hotel per person
St. Thomas
Feb 11 - Feb 15
from $778
flight + hotel per person
Havana
Santiago de Cuba
Top Caribbean Flight + Hotel Vacation Package Deals

Ocho Rios Villa at the Palms II
Price was $1,860, price is now $900 per person
$900
per person
Jan 24 - Jan 31
Roundtrip flight included
New York (NYC) to Montego Bay (MBJ)
4.8/5 Exceptional! (18 reviews)
The Palms II is the absolute best place I have found to Enjoy Ocho Rios from. The is my seventh time in Ocho Rios and I got married at a beach hotel here. Upon arrival The Palms helped to arrange airport transfer, and rides throughout our stay, even arranging food delivery because we arrived too late to get food. The service was at a cost but we were happy to pay. The house was amazing. The pictures don't even really do it justice. It was clean. The kitchen was well equipped. Would definitely return next time in Ocho Rios.
Reviewed on Jul 23, 2018

Fern Court Apartment With Oceanic View
Save 100% on your flightPrice was $1,367, price is now $684 per person
$684
per person
Jan 24 - Jan 31
Roundtrip flight included
New York (NYC) to Montego Bay (MBJ)
4.1/5 Very Good! (7 reviews)
I was very impressed with how well this place was decorated. They had everything that I expected in the amenities list in the post. I think it’s also important to know that the property is in a gated community for your extra security which gave me a feel of exclusivity during my stay. The rooms have central air and the bathrooms are beautiful. I was really pleased and I think that you would be too. Thanks again guys one love!
Reviewed on Aug 21, 2019



Ocho Rios Villa at Coolshade XI
Save 100% on your flightPrice was $1,007, price is now $575 per person
$575
per person
Feb 10 - Feb 14
Roundtrip non-stop flight included
New York (NYC) to Montego Bay (MBJ)
4.2/5 Very Good! (9 reviews)
Very good stay in Coolshade. Lorraine the manager was very attentive to our needs and helped to organize transportation and a helper to make our beds and meals for us.
Reviewed on Jan 27, 2019
Top Hotels in Caribbean
British Colonial Hilton - Nassau
Number One Bay St, Nassau
Fully refundableReserve now, pay when you stay
3.8/5 Good! (993 reviews)
"The breakfast was outstanding!! Table service was great! We stayed 5 nights and was told bc of COVID our room would be cleaned. On the fourth day we had to remind front desk. The outside bar tenders were moving like a snail and disrespectful as one of them completely ignored me when I spoke to him. ..."
Reviewed on Dec 7, 2021
Hotel El Convento
100 Cristo St, San Juan
4.5/5 Wonderful! (983 reviews)
"Very beautiful hotel. You can feel the history in the rooms and the rest of the areas. Very convenient location. Close to nice food and drink options. The restaurant/lounge in the hotel are awesome too. But the best place we liked was a cabana on 3rd floor. It was raining the evening we stayed here, ..."
Reviewed on Dec 7, 2021
Sheraton Old San Juan Hotel
100 Brumbaugh Street, San Juan
Fully refundableReserve now, pay when you stay
4/5 Very Good! (1,087 reviews)
"Excellent location, nice view. clean, fast check in and out good breakfast"
Reviewed on Dec 12, 2021
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.
Frequently asked questions
More trip options
- Bahamas
- Jamaica
- Dominican Republic
- Puerto Rico
- U.S. Virgin Islands
- Cayman Islands
- Haiti
- Trinidad and Tobago
- Turks and Caicos
- St. Kitts and Nevis
- Bermuda
- Saint Martin
- St. Vincent and the Grenadines
- Barbados
- St. Lucia
- Aruba
- British Virgin Islands
- Martinique
- St. Barthelemy
- Montserrat
- Antigua and Barbuda
- Guadeloupe
- Dominica
- Curacao
- Anguilla
- Grenada
- Sint Maarten
- Bonaire
Hotels
Hotels in Turks and CaicosAll-inclusive Resorts in Dominican RepublicAll-inclusive Resorts in Puerto RicoAll-inclusive Resorts in JamaicaAll-inclusive Resorts in U.S. Virgin IslandsAll-inclusive Resorts in ArubaAll-inclusive Resorts in BahamasPuerto Rico Island All-inclusive ResortsAll-inclusive Resorts in Turks and Caicos