Caribbean Vacation Packages

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Top vacation destinations in Caribbean

Bayahibe Beach which includes general coastal views
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Punta Cana

Punta Cana

Top Caribbean Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade

Ocho Rios Villa at Coolshade

3.5 out of 5
Price was CA $2,971, price is now CA $1,453 per person
CA $1,453
per person
May 12 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
6/10 (18 reviews)
The host was wonderful and quite responsive. I will definately stay again and highly recomend.

Reviewed on Mar 18, 2023

Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
Price was CA $3,700, price is now CA $1,783 per person
CA $1,783
per person
May 12 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
No reviews
Ocho Rios Ocean View Villa at The Palms

Ocho Rios Ocean View Villa at The Palms

4 out of 5
Price was CA $3,334, price is now CA $1,607 per person
CA $1,607
per person
May 12 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
6.4/10 (14 reviews)
Clean, great customer service. Most importantly we felt safe. Would definitely stay again and again!!

Reviewed on Oct 10, 2024

2 Bdrm Apartment at Runaway Bay

2 Bdrm Apartment at Runaway Bay

3.5 out of 5
Price was CA $3,078, price is now CA $1,502 per person
CA $1,502
per person
May 12 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Price was CA $3,597, price is now CA $1,758 per person
CA $1,758
per person
May 12 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
No reviews

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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.

Things to do in Caribbean

The Caribbean offers an array of exciting activities for every traveller. Indulge in wellness retreats that rejuvenate the mind and body, or embark on thrilling jet skiing and kayaking adventures across stunning waters. In the evenings, enjoy vibrant live music that captures the island spirit. Don't forget to relax on the fantastic beaches, where you can soak up the sun and savour the breathtaking views. It's the perfect getaway for relaxation and adventure.

Shopping

The Renaissance Mall Aruba offers a vibrant shopping experience with entertainment and family-friendly options. Visit the Straw Market for local crafts and unique souvenirs, capturing the essence of Caribbean culture. For everyday needs, Mega Mart provides a convenient shopping solution in the area.

Recreation

Experience rejuvenation at Queen's Park Savannah, where you can unwind in lush surroundings and enjoy yoga sessions. At Divi Golf and Beach Resort, engage in leisurely rounds of golf surrounded by stunning landscapes. For sports enthusiasts, Quisqueya Stadium offers thrilling events that energize the spirit.

Adventure

Sirenis Aquagames Water Park offers thrilling water slides and family-friendly attractions, perfect for a fun-filled day. Mystic Mountain provides an exhilarating adventure with zip-lining and bobsledding through lush landscapes. At Stingray City, you can swim and interact with friendly stingrays in a unique underwater experience.

Nightlife

The Caribbean nightlife offers vibrant experiences. Start with a drink at Floyd's Pelican Bar, known for its romantic and entertaining atmosphere. Then, enjoy the unique ambiance at Magic Ice Gallery. For an unforgettable night, dance at Coco Bongo Punta Cana, where the city vibes truly come alive.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Caribbean

The Caribbean offers a vibrant mix of attractions for tourists, including stunning beaches, picturesque bays, and historic churches. Whether you seek relaxation on the beach, cultural experiences, or outdoor adventures, there's something for everyone. Be sure to explore local Caribbean resorts to enhance your stay and fully enjoy the beauty and charm of this tropical paradise.

  • Eagle Beach: Experience the stunning soft white sands and turquoise waters of Eagle Beach, renowned for its serene atmosphere and vibrant beach vibes. This picturesque spot is perfect for sunbathing, swimming, or simply enjoying the breathtaking sunset views.
  • El Yunque National Forest: Discover the lush landscapes of El Yunque National Forest, a true eco-friendly oasis. With diverse flora and fauna, towering trees, and scenic trails, this rainforest offers an unforgettable outdoor adventure filled with hiking, waterfalls, and rich biodiversity.
  • Magens Bay Beach: Relax at Magens Bay Beach, a stunning bay known for its calm waters and scenic beauty. Ideal for outdoor activities, this beach is perfect for swimming, kayaking, or lounging while surrounded by lush hills and vibrant scenery.

Best time to go to Caribbean

The best time to visit Caribbean can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Caribbean falls in September, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Caribbean falls in November, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January79.3°F (26.3°C)No RainMostly SunnySlightly HighAverage
February78.8°F (26.0°C)No RainMostly SunnyAverageSlightly High
March79.2°F (26.200000000000003°C)No RainMostly SunnyAverageSlightly High
April80.1°F (26.700000000000003°C)Light RainMostly SunnyAverageAverage
May80.4°F (26.9°C)Light RainMostly SunnySlightly LowAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.2°F (27.9°C)Light RainMostly SunnySlightly HighAverage
August82.8°F (28.200000000000003°C)Light RainMostly SunnyAverageAverage
September82.9°F (28.3°C)Light RainMostly SunnySlightly HighSlightly Low
October82.6°F (28.1°C)Light RainMostly SunnySlightly LowSlightly Low
November78.3°F (25.700000000000003°C)Light RainMostly SunnySlightly LowSlightly Low
December79.5°F (26.4°C)No RainMostly SunnyAverageSlightly High

Tips to save on your trip to Caribbean

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Caribbean during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $552 per night from Mar 25 to Mar 26
CA $552
CA $723 total
Mar 25 - Mar 26
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Beautiful property in a perfect location if you plan to visit Old San Juan. Restaurant is wonderful.

Reviewed on Feb 14, 2026

Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St Nassau
The price is CA $308 per night from Mar 3 to Mar 4
CA $308
CA $456 total
Mar 3 - Mar 4
includes taxes & fees
8.6/10 Excellent! (2,290 reviews)
Nice place to visit.

Reviewed on Feb 24, 2026

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 $324 per night from Mar 17 to Mar 18
CA $324
CA $411 total
Mar 17 - Mar 18
includes taxes & fees
9/10 Wonderful! (1,537 reviews)
Very late check-in, friendly staff. Great location for getting on cruise ship.

Reviewed on Feb 24, 2026

Hotel Rumbao, a Tribute Portfolio Hotel
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