Caribbean Vacations & Trips from $522

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Explore Caribbean vacation packages for unforgettable moments

Get ready for a breathtaking journey through the Caribbean, where idyllic beaches, vibrant cultures, and lush landscapes await. This guide to the top vacation destinations in the Caribbean promises an unrivaled escape into paradise. Whether you're looking to unwind on the serene sands of the BahamasOpens in a new window, revel in the cultural festivities of JamaicaOpens in a new window, or explore the historic richness of Puerto RicoOpens in a new window, there's a perfect Caribbean vacation deal for everyone. Explore these enchanting Caribbean vacation destinations and find your ideal spot for relaxation, adventure, or both in this sun-kissed region.

Top destinations in Caribbean

Condado Beach which includes general coastal views and a coastal town
FlightsFlightsHotelsHotels

San Juan

San Juan

The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Urbana Hotel

Urbana Hotel

2 out of 5
Puerta de Tierra
Save 100% on your flight
per person
May 27 - Jun 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
8.4/10 Very Good! (194 reviews)
Good place to go for a night in San Juan. Pretty basic accommodations but they were comfortable. In an okay area - have to walk a bit or use scooters to see touristy stuff.

Reviewed on Mar 24, 2025

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9/10 Wonderful! (61 reviews)
I absolutely love the property and the employees.. the only thing I was concerned about was the air conditioning in the rooms.. it was very hot but everything else was beautiful!

Reviewed on Mar 24, 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9.2/10 Wonderful! (82 reviews)
This resort is absolutely beautiful! The grounds are beautiful - full of plants, trees and flowers. The property is very large but easy to navigate.This resort would benefit from a map on the app or on paper. But what really makes this resort the best, is the staff!!The welcoming crew is fantastic - we received cocktails during check-in. Ricardo is your guy! He ensured we had a smooth check in experience and gave us many tips and information about the resort grounds, restaurants, bars, pools and services offered. We had the pleasure of having 3 butlers included in our over water bungalow package. Navado, Glaister & Ashley all had excellent customer service and took care of many food reservations, golf cart transportation, coffee and breakfast in the morning, off sight excursions and many other requests we had during our visit. They were always willing to help and had many facts and information regarding the resort and mangrove history. The bar tenders are top notch from customer service, local recommendations and drink recommendations! We tried a different drink each time. Make sure you stop by the platinum bar and see Oshe! His customer service is stellar, he keeps the jokes flowing, he called us by name and never had a bad recommendation! Our evening go to was to visit Omar & Franz at the Piano Bar - they kept the laughs and drinks flowing! This resort is highly recommended and the staff here is the reason! Genuine people who provide top tier hospitality! Ya mon!

Reviewed on Mar 23, 2025

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...

Reviewed on May 8, 2019

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
per person
May 18 - May 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nassau (NAS)
8/10 Very Good! (2,853 reviews)
small property not a lot of area to walk around

Reviewed on Mar 24, 2025

Best Places to Vacation in Caribbean

An image of bahamas

Find fun in the sun with Bahamas vacation packages

The Bahamas are a popular vacation destination for people all throughout the states, thanks to the islands' tropical climates. What was once a pirate cove has since become home to luxury resorts and beachfront experiences defined by welcoming turquoise waters you won't want to miss out on. Plus, you'll find numerous watersports available here if you want to add some more thrills to your vacation.

An image of us virgin islands

Relax with US Virgin Islands vacation packages

When you visit the US Virgin Islands, you'll find yourself in a Caribbean paradise. Much of the island is developed with travelers in mind, which is quite luxurious. Yacht charters are common here, but you can also simply relax at the beach. The islands are also known for rum distilling, so be sure to try out the local recipe during your visit.

An image of jamaica

Explore the island with Jamaica vacation packages

Jamaica is an exciting country that offers stunning cityscapes, welcoming beaches, and impressive natural features. In cities like Kingston, you'll find fascinating museums and delicious food, but that's just the beginning. The beaches have all the Caribbean flair you might expect, but inland adventure is also available. The dense forests are home to diverse wildlife, and you can see it all by trekking through on a hike.

An image of puerto rico island

Enjoy relaxation and adventure with a Puerto Rico Island vacation

Puerto Rico Island is packed full of fun things to do, whether you're interested in history, relaxation, or adventure. The beaches here are some of the best in the world, allowing for swimming, snorkeling, and water sports like jet skiing. The history here is well preserved and lets you see old examples of colonial architecture as well as forts that are still standing.

Find the Best Caribbean Vacation Packages

Best months to visit Caribbean

Looking for the best time to visit Caribbean? Our table will help you. Caribbean boasts a year-round average temperature of 80.6°F, reaching a peak of 82.9°F in September, its warmest month, and dropping to an average low of 78.3°F in November, the coolest month. The annual rainfall averages 81.6mm, with September experiencing the heaviest showers, while February is the driest month.

Monthcalendar iconTemperature (Fahrenheit)temperature iconRainfallrain iconCloud coveragecloud icon
January79.3No Rain (Dry)Mostly Sunny
February78.8No Rain (Dry)Mostly Sunny
March79.2No Rain (Dry)Mostly Sunny
April80.1Light RainMostly Sunny
May80.4Light RainMostly Sunny
June81.7Light RainMostly Sunny
July82.2Light RainMostly Sunny
August82.8Light RainMostly Sunny
September82.9Light RainMostly Sunny
October82.6Light RainMostly Sunny
November78.3Light RainMostly Sunny
December79.5No Rain (Dry)Mostly Sunny

How to save money on a vacation to Caribbean

  • Combine your flights with hotels or car rentals to save money and get great package deals through Expedia's OneKey program.
  • Take advantage of Expedia's OneKey program to collect points and save money on your Caribbean travels.
  • Utilize the helpful search filters on Expedia to find the perfect accommodation within your price range.
  • Consider traveling to the Caribbean during the off-peak season from October to December for better deals and less crowded destinations.
  • Use the search filter for price limits on Expedia to find a vacation package that suits your budget.
  • Discover the best vacation experience for you by using the travel experience filter on Expedia, whether it's a family, romantic, or adventurous getaway.

Why visit Caribbean

Caribbean cuisine 
No Caribbean trip is complete without savoring the region's diverse flavors. From Jamaica's spicy jerk chicken to the fresh seafood of the Grenadines, each meal offers a unique taste adventure. Experience the culinary diversity that makes Caribbean cuisine truly unforgettable.  

Cultural festivals 
Participate in vibrant local festivals like Trinidad's Carnival or Barbados's Crop Over. These events showcase music, dance, and cuisine, offering a glimpse into the Caribbean's joyous spirit and creativity. Enjoy the lively traditions and colorful atmosphere that define these cultural celebrations.  

Relaxing retreats 
If you're seeking relaxation, you'll find it in spades at the numerous Caribbean spas and wellness retreats offering soothing treatments. These sanctuaries, which use local ingredients like aloe and coconut, provide the perfect escape to rejuvenate your mind and body amidst tropical tranquility.  

Underwater adventures 
In the Caribbean's crystal-clear waters, thrill-seekers have endless opportunities for snorkeling, scuba diving, and parasailing. Explore the vibrant coral reefs teeming with colorful fish and encounter exotic marine life. Each dive promises a unique and memorable adventure.  

Caribbean Hotel Deals

Hotel El Convento
Hotel El Convento
4.5 out of 5
100 Cristo St, San Juan
Fully refundableReserve now, pay when you stay
The price is $360 per night from Apr 15 to Apr 16
$360
includes taxes & fees
$331 per night
Apr 15 - Apr 16
8.6/10 Excellent! (1,001 reviews)
"Fantastic location and beautiful architecture. Offers free water bottles, hot coffee and tea, and free wine and cheese. Soundproof is great."

Reviewed on Mar 20, 2025

Hotel El Convento
British Colonial - Nassau
British Colonial - Nassau
4 out of 5
Number One Bay St, Nassau
Fully refundableReserve now, pay when you stay
The price is $298 per night from Apr 1 to Apr 2
$298
includes taxes & fees
$272 per night
Apr 1 - Apr 2
8.4/10 Very Good! (1,391 reviews)
"We enjoyed the property and amenities,especially being in the down town area. We was disappointed with housekeeping. Our room wasn't clean daily and several days towels weren't replenish as advertised."

Reviewed on Mar 23, 2025

British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel
Hotel Rumbao, a Tribute Portfolio Hotel
4 out of 5
100 Brumbaugh Street, San Juan, Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $287 per night from Apr 21 to Apr 22
$287
includes taxes & fees
$264 per night
Apr 21 - Apr 22
8.8/10 Excellent! (820 reviews)
"Excellent place for our family to stay before our cruise!"

Reviewed on Mar 21, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 80,060 properties in Caribbean
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Caribbean vacation package cost?
Custom make your Caribbean vacation package from only $522. Choose from any combination of rental cars, flights and hotels to create the getaway you’ve been dreaming about. Don’t forget to add on a few experiences or tours!
How do I get a cheap travel package to Caribbean?
Search for flights that suit your busy schedule, add a hotel room to your booking and watch the savings pile up with a Caribbean vacation package. It’s that simple! From hotels and flights to activities and rental cars, Expedia makes traveling on a budget easy. And with more than 550 air carriers and 1,000,000 hotels all over the world to pick from, you won’t be short of choice.
How far in advance should I book my Caribbean vacation?
While not all air carriers advertise ticket prices early, customers are usually able to start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic deals. If you’re booking late, you may still be in luck. Sometimes the lowest prices emerge just weeks prior to departure.
What does an Expedia Caribbean travel package include?
It comes down to what you’re looking for. If you’re traveling alone, you might decide to combine hotels and flights. Taking the entire family to Caribbean? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the freedom and flexibility to build your own travel package.
What should I know before booking a Caribbean travel package?
Get set to save with an Expedia travel package. Combine your airfares, rental cars and hotels and enjoy fantastic discounts. You’re not restricted to hotels, however. We have beachside condos, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a Caribbean Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
Does Expedia offer Book Now, Pay Later Caribbean vacation packages?
Your bank balance shouldn’t stop you from having a fabulous vacation, so Expedia has devised a solution to help. Thanks to our partnership with online lender Affirm, it’s easier than ever to book an amazing getaway that won’t hurt your savings. Simply Book Now, Pay Later and take the financial stress out of planning for your journey.
If I'm not able to travel, can I cancel my Caribbean vacation package?
Certainly, and we’re here to help. You may be able to cancel or change your Caribbean vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, browse our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.