Caribbean Vacations & Trips from $935

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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.
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
Aug 29 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.8/10 Excellent! (222 reviews)
Exceptional Stay with Thoughtful Butler Service! We had an unforgettable stay at Princess Grand Resort Jamaica! The resort is absolutely gorgeous, the food was delicious, and every part of the all-inclusive experience was seamless and luxurious. The true stars of our vacation were our incredible butlers, Carl and Daviesha. Their service was above and beyond-professional, warm, and incredibly thoughtful. One of the highlights was returning to our room to find a beautiful thank-you surprise waiting: rose petals, and a relaxing bubble bath already drawn. It was such a kind and personal gesture that made us feel so appreciated and pampered. Carl and Daviesha made every day feel special, and their attention to detail is unmatched. This was hands down one of the best service experiences we've ever had. If you're looking for a luxurious getaway with genuine, five-star hospitality, Princess Grand Resort Jamaica is the perfect choice. We can't wait to return!

Reviewed on Jul 11, 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
Aug 29 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9.2/10 Wonderful! (209 reviews)
Love the ambiance and welcoming atmosphere of the hotel.

Reviewed on Jul 11, 2025

Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.8/10 Excellent! (1,494 reviews)
The drinks option were good, there were enough activities to do, but this is not the place to bring the kids for a family outing if you’re looking for luxury. The food options were subpar and aesthetics could improve compared to similar tier resorts. They used spaghetti noodles for pad Thai at one of the reservation restaurants, like cmon! Also, you can only book one day ahead of time? We do realize there are 736 rooms right? Sea urchins are also on the beach so be careful, the resorts could do a better job warning guests! I got spiked before I even checked in. Noise level could be an issue for a RIU palace (family oriented) resort. How about we standardize rules and make sure the staff enforces it? It can be very inconsistent at times. Pools closes at 6pm, like we still got sun out!! Please extend to 8pm. No Q Tip, make up remover, body lotion, or shower cap in the room. This resort open in May 2026 so it has to do with the staff training …. some guest in the buffer area are straight up rude or doesn’t seem like they want to be there.

Reviewed on Jul 12, 2025

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on May 1, 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
$243 nightly
The price is $265 total per night from Aug 10 to Aug 11
$265 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,003 reviews)
Perfect location in Old San Juan
"An absolutely perfect location in Old San Juan. Within walking distance of all of the historic city center. Cool old historic hotel. We loved it."

Reviewed on Jul 7, 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
$244 nightly
The price is $267 total per night from Aug 3 to Aug 4
$267 total
Aug 3 - Aug 4
Total includes taxes and fees
8.6/10 Excellent! (1,745 reviews)
"Excellent staff! Great location and lovely property"

Reviewed on Jul 11, 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
$225 nightly
The price is $245 total per night from Aug 4 to Aug 5
$245 total
Aug 4 - Aug 5
Total includes taxes and fees
9/10 Wonderful! (1,017 reviews)
"Loved this hotel"

Reviewed on Jul 10, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 80,759 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 $935. 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.