Caribbean Vacations & Trips from $365

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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

The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Urbana Hotel
Alamanda Cottage at Serenity
Coral Costa Caribe Beach Resort - All Inclusive
Riu Palace Paradise Island - Adults Only - All Inclusive
El Colonial - Adults Only

Top Vacation Destinations 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.

Discover the ultimate island paradise with a vacation in the Caribbean

Get ready for an unforgettable Caribbean vacation 

Prepare to immerse yourself in the unparalleled allure of the Caribbean—a region synonymous with crystal-clear waters, sun-soaked beaches, and a vibrantly diverse culture. Spanning numerous islands, each with its unique charm, a Caribbean vacation offers a kaleidoscope of experiences from relaxing beach getaways to thrilling adventures. Whether it's a long-awaited family vacation, a romantic escape, or an adventurous solo trip, a Caribbean getaway promises something special for every traveler. 
 

Seamless Caribbean vacations with flights + hotels 

Planning your dream Caribbean trip is a breeze with tailored vacation packages. Select from an array of Caribbean travel deals. You can sometimes also combine flights and hotels for exceptional savings on your Caribbean getaway. Imagine stepping out from your room onto the powdery sands of Barbados, diving into the azure waters of the Bahamas, or exploring the lush rainforests of St. Lucia—all made easy and affordable with these exclusive travel deals. 

Your dream Caribbean vacation itinerary 

  • Days 1–3: Soak up the sun in the Bahamas Begin your Caribbean adventure in the Bahamas, choosing the fast track, with the glitz, glamour, and adventure of Paradise Island or the slow life, with the tranquil beauty of Abaco Island that invites you to relax and explore. Discover the underwater caves or enjoy the local Junkanoo Festival, immersing yourself in the festive culture. 
  • Days 4–6: Discover Puerto Rico's rich history and natural beauty Next, immerse yourself in the historic charm of Ponce's elegant plazas and the breathtaking beauty of the Guánica Dry Forest. Puerto Rico offers a seamless blend of rich cultural heritage and stunning natural landscapes, which you'll love if you appreciate history intertwined with the serenity of nature. 
  • Days 7–9: Experience the vibrant life in Jamaica Move on to Jamaica, where rhythmic reggae beats and spicy jerk flavors await. Spend your days exploring the Blue Mountains or relaxing in the laid-back atmosphere of Negril's Seven Mile Beach. 
  • Days 10–12: Unwind in the luxurious tranquility of the British Virgin Islands Wind down your trip in the British Virgin Islands. Sail from Tortola to Virgin Gorda's Baths for a day of snorkeling in secluded coves and marveling at natural rock formations. 

Special experiences on your Caribbean vacation 

Bioluminescent Bay, Puerto Rico Experience a magical night in the glowing waters of Bioluminescent Bay. Kayak under the stars as every paddle stroke lights up the water with a blue-green glow, a result of tiny, luminous organisms. It's not just a trip; it's a glowing testament to nature's wonders and a must-see spectacle. 

The Pitons, St. Lucia Rising majestically above the Caribbean Sea, the Pitons are St. Lucia's twin volcanic spires. These iconic peaks are a treat for the eyes and a playground for the soul. Whether you're hiking or viewing them from a boat, they offer breathtaking scenery and a perfect photo op that encapsulates the island's majestic beauty. 

Dunn's River Falls, Jamaica This cascading waterfall is one of Jamaica's national treasures. Climb the naturally terraced steps, or simply relax in the refreshing pools. It's a place where you can literally immerse yourself in the island's vibrant energy and wash away the ordinary. 

Horseshoe Reef, The Tobago Cays, St. Vincent and the Grenadines Snorkeling in the pristine waters of Horseshoe Reef in the Tobago Cays is a singular experience. This barrier reef has a kaleidoscope of coral gardens teeming with colorful marine life. It's a vibrant underwater world where you'll encounter unbridled natural beauty. 

Willemstad, Curaçao Stroll through the streets of Willemstad, an UNESCO World Heritage Site, and marvel at the pastel-colored Dutch colonial architecture. This bustling port city is a canvas of cultural diversity, offering lively markets, museums, and a charming floating bridge. Willemstad is a vibrant celebration of history and heritage. 

Book your vacation in the Caribbean today 

With this extensive selection of Caribbean travel deals, planning your tropical escape has never been easier. Choose from a variety of Caribbean islands vacation packages that cater to all preferences and budgets. From last-minute vacation deals in the Caribbean to all-inclusive luxury stays, find great value and convenience for your travel needs. 

Embark on your Caribbean getaway, where the promise of sun, sea, and sand creates the perfect setting for unforgettable memories. Whether you're exploring vibrant cultures, enjoying natural beauty, or just unwinding on the beach, a vacation in the Caribbean offers a taste of paradise. So pack your bags, bring your sense of adventure, and let these vacation islands in the Caribbean transform your travel dreams into cherished experiences. 

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 $324 per night from Aug 7 to Aug 8
$324
per night
Aug 7 - Aug 8
8.6/10 Excellent! (1,002 reviews)
"Great experience"

Reviewed on Jul 20, 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 $262 per night from Jul 29 to Jul 30
$262
per night
Jul 29 - Jul 30
8.6/10 Excellent! (625 reviews)
"Property is newly renovated and located in downtown which msde shopping easy."

Reviewed on Jul 25, 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 refundableReserve now, pay when you stay
The price is $241 per night from Aug 5 to Aug 6
$241
per night
Aug 5 - Aug 6
8.8/10 Excellent! (260 reviews)
"Close to everything"

Reviewed on Jul 26, 2024

Hotel Rumbao, a Tribute Portfolio Hotel
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.

Frequently asked questions

How much does a Caribbean vacation package cost?
Perhaps less than you imagined — from a low $365, 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.