Caribbean Vacation Packages

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Top vacation destinations in Caribbean

A marina with a white boat named 'Achina' docked, surrounded by palm trees and a building with a green roof.

Punta Cana

Punta Cana
A pier with kayaks and a sailboat.

Montego Bay

Montego Bay
A cruise ship docked at a port with a clear blue sea and a small island in the background.

Nassau

Nassau
A beach with clear turquoise water, white sand, and green foliage in the foreground.

St. Thomas

St. Thomas
A tropical beach with turquoise waters, green hills, and a clear sky.

St. John

St. John
A beach with clear turquoise water, a sandy shore, and a city skyline with tall buildings including a Marriott hotel.

San Juan

San Juan
A beach with clear turquoise water, a person sunbathing, and palm trees in the background.

Oranjestad

Oranjestad
Turquoise waters, green islands, and lush vegetation.

Providenciales

Providenciales
A sandy beach with clear blue water, palm trees, and people enjoying the beach.

Noord

Noord

Top Caribbean Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

Isla Verde
CA $1,316
per person
Oct 18 - Oct 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

CA $2,410
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,007 reviews)
Coral Costa Caribe Beach Resort - All Inclusive

Coral Costa Caribe Beach Resort - All Inclusive

Villas Del Mar
CA $1,485
per person
Oct 1 - Oct 8
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Santo Domingo (SDQ)
8/10 Very good! (2,643 reviews)
Everything

Reviewed on Aug 10, 2026

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

CA $1,631
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...

Reviewed on May 8, 2019

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

CA $2,590
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Nassau (NAS)
8/10 Very good! (4,039 reviews)
Last minute getaway and it was not all it could have been. After a day or two I had to change rooms because there were multiple roaches in my room when I returned after dinner. The new room I was moved to had a door that did not lock at all.

Reviewed on Aug 11, 2026

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

100 Cristo St San Juan
Fully refundableReserve now, pay when you stay
CA $243
CA $318 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
"Awesome environment"

Reviewed on Aug 10, 2026

Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
CA $233
CA $362 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (2,887 reviews)
"Last night the fire alarm went off all night long, could not sleep, than again in the morning. at checkout even after I had pre paid all charges with Expedia, they charged my card again for resort fee when my reservation was clearly written that resort fee was included, still waiting for hotel ..."

Reviewed on Aug 11, 2026

British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
CA $231
CA $310 total
Aug 31 - Sep 1
includes taxes & fees
Hotel Rumbao, a Tribute Portfolio Hotel
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Stay near popular Caribbean attractions

An old church with a tiled roof, stone walls, and two bell towers.

Altos de Chavon Village

A replica 16th-century Mediterranean village perched on a rocky outcrop above the River Chavón.
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A beach scene with a flag, beach chairs, umbrellas, and a vendor cart.

Eagle Beach

9.4/10 (6,014 reviews)
Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.
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A cruise ship docked near a coastal city with buildings and palm trees.

Port of San Juan

9.0/10 (16,423 reviews)
Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene.
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A beach with people walking, clear blue water, and green vegetation in the foreground.

Grace Bay Beach

9.8/10 (5,552 reviews)
Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.
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A coastal resort area with a beach, clear turquoise waters, and a clear sky.

Punta Cana Beach

8.8/10 (30,329 reviews)
Nothing says vacation like spending a lazy day at Punta Cana Beach, a popular beach in Punta Cana. Amble around this romantic area's seaside and enjoy its lively bars.
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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.