Caribbean Vacations & Trips from $457

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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 Bahamas, revel in the cultural festivities of Jamaica, or explore the historic richness of Puerto Rico, 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
San Juan Antiguo
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
8.6/10 Excellent! (77 reviews)
Super place for the price, great coffee and free beers, friendly staff, free parking

Reviewed on Sep 10, 2024

El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
Old San Juan
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
9.6/10 Exceptional! (1,018 reviews)
I love the island hospitality ‼️no complaints

Reviewed on Sep 21, 2024

Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
No reviews
Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
per person
Nov 30 - Dec 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nassau (NAS)
8/10 Very Good! (2,514 reviews)
The staff was outstanding. The food was excellent.

Reviewed on Sep 28, 2024

San Agustin Apartments

San Agustin Apartments

3 out of 5
San Juan Antiguo
Save 100% on your flight
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
9/10 Wonderful! (175 reviews)
Property well maintained, however parking lot was a mess and there was damage to my rental. Additionally, items I purchased were taken when room was cleaned.

Reviewed on Sep 25, 2024

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.

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

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 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.  

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 $243 per night from Sep 30 to Oct 1
$243
includes taxes & fees
$223 per night
Sep 30 - Oct 1
8.6/10 Excellent! (1,002 reviews)
Great location and lovely historic building
"Location was perfect and renovation of this lovely historic building (was a convent years ago) in to a hotel was nicely done. Room was spacious and comfortable with a great view out over the church square."

Reviewed on Sep 17, 2024

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 $247 per night from Oct 7 to Oct 8
$247
includes taxes & fees
$225 per night
Oct 7 - Oct 8
8.6/10 Excellent! (839 reviews)
"British colonial very quiet clean and the staff was very Polite"

Reviewed on Sep 26, 2024

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 refundable
The price is $229 per night from Oct 7 to Oct 8
$229
includes taxes & fees
$213 per night
Oct 7 - Oct 8
8.8/10 Excellent! (337 reviews)
"Perfect location. Staff were incredible and accommodating."

Reviewed on Sep 24, 2024

Hotel Rumbao, a Tribute Portfolio Hotel
See all 77,408 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

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Frequently asked questions

How much does a Caribbean vacation package cost?
Perhaps less than you imagined — from a low $457, actually! By combining hotels, flights and car rentals into your own custom-made package, your getaway to Caribbean is just clicks away.
If I'm not able to travel, can I cancel my Caribbean vacation package?
You can cancel your Caribbean booking if your travel plans have changed. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Caribbean?
Our Caribbean vacation packages promise plenty of savings for the savvy traveler. How does up to $366 sound? That’s what you could save if you bundle your hotel, flights and tours into an affordable package. But low prices are just the beginning of your next epic adventure. Book with Expedia and and you’ll have over 550 airlines and 1,000,000 properties across the globe to choose from. No matter your style, there’s a package to suit you.
When is the best time of year to visit Caribbean?
You’ll have to consider your priorities to find the right answer. Typically, you’ll nab the best deals in , while is when prices generally rise. Caribbean draws the crowds in . If you’re in the mood for a more relaxed escape, would be a better time to pack your bags.
How far in advance should I book my Caribbean vacation?
Be rewarded with the biggest variety at the lowest prices by booking your Caribbean adventure nice and early. Air carriers tend to advertise flights anywhere up to a year before departure, so reserve your spot as soon as possible. That being said, Expedia is constantly working to give you the best deals around, so there’s never a bad time to book your dream vacation!
What does an Expedia Caribbean travel package include?
That mostly depends on you. You can choose from a range of Caribbean bundles, such as a flight, hotel and rental car. You can also book a hotel with a flight, or a rental car and a flight. Once you’ve made your booking, you can add on the fun stuff like experiences and tours. Whatever your perfect Caribbean trip looks like, get ready to save!
What should I know before booking a Caribbean travel package?
A package can be easier on the credit card than individually booking all you need for your escape. For example, combine your flights, hotels and rental cars and save a pretty penny. Whatever your vacation goals are, there’s sure to be a package within your budget.
Does Expedia offer Book Now, Pay Later Caribbean vacation packages?
Pay the full cost of your travel package when you book or spread it over several installments — it’s up to you. Every traveler has their own unique financial circumstances. It’s for that reason Expedia has joined forces with online lender Affirm to offer a Book Now, Pay Later option for all package bookings.
Can I choose my airline with a Caribbean Expedia vacation package?
You can, and with over 550 airlines to select from all over the world, you have plenty of choice. Search the available options and see which airline best suits your needs and budget.
Can I travel to Caribbean right now?
Our Covid-19 Travel Advisor is the place to go for up-to-date information about quarantine policies and travel restrictions for Caribbean. Get clued up before you go!

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.