Caribbean Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 vacation destinations in Caribbean

FlightsFlightsHotelsHotels

San Juan

San Juan

Top Caribbean Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Ironshore
per person
Sep 28 - Oct 8
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Montego Bay (MBJ)
No reviews
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Montego Bay (MBJ)
9.2/10 Wonderful! (300 reviews)
My experience was superb, the butler service was amazing, the food was amazing! I will definitely be revisiting this property. 5/5 Highly recommended property.

Reviewed on Aug. 11, 2025

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Montego Bay (MBJ)
8.8/10 Excellent! (441 reviews)
It was a wonderful experience

Reviewed on Aug. 10, 2025

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Sep 14 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,003 reviews)
Quiet peaceful property. Friendly helpful staff. Beautiful beach.

Reviewed on Aug. 10, 2025

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.

Why visit Caribbean

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 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.  

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.  

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.  

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 CA $252 per night from Sep 10 to Sep 11
CA $252
CA $330 total
Sep 10 - Sep 11
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The hotel is beautiful and the staff was so kind. The restaurant on site has great food and drinks. The location is perfect, walking distance to shops, restaurants and historical attractions."

Reviewed on Aug. 5, 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 CA $219 per night from Aug 31 to Sep 1
CA $219
CA $344 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,866 reviews)
"Amazing property. Would definitely return."

Reviewed on Aug. 10, 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 CA $243 per night from Sep 9 to Sep 10
CA $243
CA $318 total
Sep 9 - Sep 10
includes taxes & fees
8.8/10 Excellent! (1,081 reviews)
"Excellent!"

Reviewed on Aug. 7, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 80,916 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
Family Vacations
Family Vacations

Other vacations you might like

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