Caribbean Vacations & Trips from $577

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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 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 destinations in Caribbean

The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Isla Verde Beachfront Retreat With Parking
Blue Seas Two Unity Hall
Sunset at the Palms Resort - Adults Only - All Inclusive
Coral Costa Caribe Beach Resort - All Inclusive
Ocho Rios Villa at The Palms

Best Places to Vacation in Caribbean

Things to do in Caribbean

The Caribbean offers a perfect blend of relaxation and adventure, featuring wellness retreats that rejuvenate the spirit. Visitors can engage in various activities such as snorkeling, sailing, and vibrant cultural festivals showcasing local traditions. Explore stunning hiking routes through lush landscapes and discover scenic parks perfect for unwinding amidst nature. Each island presents a unique experience that captures the essence of paradise.

Shopping

At Renaissance Mall Aruba, enjoy a vibrant atmosphere with entertainment and family-friendly options. For a unique experience, visit the Straw Market, where you can find local crafts and souvenirs. Don't miss Distrito T-Mobile for a mix of shopping and city vibes, perfect for families and business travelers alike.

Recreation

Experience the El Conquistador Golf Course, where you can enjoy a round of golf amidst breathtaking Caribbean scenery. For relaxation, visit Scape Park, a serene haven offering wellness activities like yoga and nature walks. Lastly, catch an exciting event at the National Stadium, perfect for sports enthusiasts.

Adventure

Experience the thrill of Sirenis Aquagames Water Park with its exciting slides and family-friendly attractions. Discover adventure at Mystic Mountain, where you can zip line through lush landscapes. Swim with graceful stingrays at Stingray City, combining underwater exploration with exhilarating sports vibes.

Nightlife

In the Caribbean, experience vibrant nightlife at Coco Bongo Punta Cana, where romance and city vibes collide with thrilling entertainment. Visit Floyd's Pelican Bar and Magic Ice Gallery for a laid-back atmosphere, offering drinks and a lively ambiance perfect for enjoying the local nightlife.

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

Find the best attractions in Caribbean

The Caribbean is a vibrant paradise featuring stunning beaches, picturesque bays, and historic churches, perfect for travelers seeking culture and outdoor experiences. With a variety of attractions and activities, visitors can explore beautiful destinations while enjoying the sun and sea. Consider looking into Caribbean vacation packages to enhance your experience and make the most of your trip to this idyllic region.

  • Eagle Beach: Experience the serene beauty of Eagle Beach, known for its soft white sands and crystal-clear waters. This beach offers a relaxing atmosphere, perfect for sunbathing, swimming, and enjoying stunning sunsets.
  • El Yunque National Forest: Immerse yourself in the lush greenery of El Yunque National Forest, where you can hike through scenic trails, discover waterfalls, and spot diverse wildlife. It's an eco-friendly paradise for nature lovers and adventure seekers alike.
  • Magens Bay Beach: Enjoy the picturesque views at Magens Bay Beach, a stunning bay with calm waters ideal for swimming and water sports. The surrounding scenery and beach ambiance make it a perfect spot for relaxation and outdoor fun.

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.

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.

Find the Best Caribbean Vacation Packages

Why visit Caribbean

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.  

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.  

Caribbean Hotel Deals

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
$379 nightly
The price is $413 total per night from Nov 9 to Nov 10
$413 total
Nov 9 - Nov 10
Total with taxes and fees
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
$318 nightly
The price is $348 total per night from Nov 5 to Nov 6
$348 total
Nov 5 - Nov 6
Total with taxes and fees
8.6/10 Excellent! (3,153 reviews)
"everything was great. def will come back"

Reviewed on Nov 4, 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
$202 nightly
The price is $224 total per night from Nov 29 to Nov 30
$224 total
Nov 29 - Nov 30
Total with taxes and fees
9/10 Wonderful! (2,005 reviews)
"Great location right across the street for Old San Juan port."

Reviewed on Nov 4, 2026

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 do vacation package prices compare across popular destinations in the Caribbean?
For a Caribbean vacation package, prices for a week-long trip typically range from around $1,150 to $2,350 per adult, depending on your chosen destination. San Juan generally offers the lowest typical prices, while Noord tends to be on the higher end.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Caribbean vacation package?
When you bundle, you can save up to 30%*. To save money on a Caribbean package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Caribbean vacation package?
A Caribbean vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations.

In Punta Cana, most hotels offer airport shuttle service to and from Punta Cana International Airport (PUJ), and most also include free breakfast. In San Juan, nearly all hotels provide airport shuttle service to and from Luis Muñoz Marín International Airport (SJU), and about half include free breakfast. For Montego Bay, most hotels offer airport shuttle service to and from Sir Donald Sangster International Airport (MBJ), and most also provide free breakfast.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
Which destinations in the Caribbean offer the best-value vacation package deals?
San Juan, St. Thomas, Punta Cana, Sosúa, and Montego Bay are some of the top destinations for cheap Caribbean vacation package deals. For an affordable weekend getaway, San Juan is often among the most budget-friendly options, with package prices starting around $500 per adult. For notable bundle savings, Paradise Island is often among the best options, with flight-and-hotel bundles saving around $265 per adult.

Browse cheap vacation packages in the Caribbean on Expedia to compare current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
When is the best time to visit the top destinations in the Caribbean?
The best time for a Caribbean vacation package depends on which destination you choose.

Punta Cana is busiest in June, July, and December, with average temperatures around 82°F in July and 78°F in December. If you'd prefer fewer crowds, January and from September to October are quieter, with average temperatures around 77°F in January.

San Juan sees its highest demand in March, July, and December, with average temperatures around 77°F in December and 82°F in July. January also brings the Fiestas de la Calle. For a quieter trip, January and from September to October are less busy, with average temperatures around 81°F in October.

Noord is most popular in March, July, and August, when average temperatures are around 82°F in August and 82°F in July. If you'd prefer fewer visitors, from January to February are quieter, with average temperatures around 79°F in February.

Montego Bay is busiest in March, June, and December, with average temperatures around 78°F in December and 82°F in June. For a quieter experience, January and from October to November are less crowded, with average temperatures around 77°F in January.
What package types are available across the top destinations in the Caribbean?
The Caribbean offers a variety of vacation package types across its popular destinations like Punta Cana, Noord, San Juan, Montego Bay, and St. Barthelemy:
  • All-inclusive: In Punta Cana, the 4-star Majestic Colonial Punta Cana - All Inclusive, rated 8.5 out of 10 by travelers, features a kids club and hot tub, with travelers noting the excellent location and helpful staff.
  • Couples: In Noord, the 4.5-star Hyatt Regency Aruba Resort and Casino, rated 8.7 out of 10 by travelers, provides a spa and hot tub, and travelers often praise the nice staff and great food.
  • Budget: For value-focused stays, The Looking Glass Hotel in San Juan, rated 8.7 out of 10 by travelers, offers free WiFi, with travelers frequently praising its fantastic location and great breakfast.
  • Family: In Montego Bay, the 4.5-star Hotel 39 Jamaica, rated 7.8 out of 10 by travelers, provides family rooms and a game room, with travelers frequently praising the fantastic staff and great food.
  • Luxury: In St. Barthelemy, the 5-star Le Toiny Hôtel & Beach Club, rated 9.7 out of 10 by travelers, features a spa and kitchenettes, and travelers highlight the amazing facilities and attentive staff.
Which destinations should I consider for a Caribbean vacation?
When planning a Caribbean vacation, consider these destinations based on your travel style:
  • Punta Cana: A popular package base, this destination is primarily known for its beautiful beaches and a wide array of outdoor and sports activities, making it ideal for a classic sun-and-sand getaway.
  • San Juan: For those seeking a blend of beach relaxation and urban exploration, San Juan is a popular package base offering vibrant city attractions and family-friendly options alongside its coastal charm.
  • Paradise Island: This popular package base is primarily known for its city and urban attractions, making it a great choice for romantic getaways and travelers who enjoy a lively atmosphere with easy access to beaches.
  • Sosúa: A good lodging base with many hotel choices, Sosúa is primarily family-friendly, offering beaches, city attractions, and a setting that also suits romantic trips.
Is Caribbean better suited for a beach vacation or a cultural trip?
The Caribbean offers a diverse mix, making it well-suited for both beach vacations and cultural trips, depending on the specific island or city you choose. Many destinations, like Punta Cana, are primarily known for their stunning beaches and outdoor activities, perfect for sun-and-sand getaways.

However, cities such as San Juan in Puerto Rico provide a rich cultural experience with historic sites like the Port of San Juan and urban attractions. Similarly, Montego Bay in Jamaica blends its beautiful beaches with cultural attractions like the Rose Hall Great House. Your Caribbean vacation can be tailored to prioritize either relaxation on the sand or exploration of local history and city life.
Which airports serve the main destinations in the Caribbean?
For a Caribbean vacation, several international airports serve the main destinations. San Juan (SJU-Luis Munoz Marin Intl.) is a primary gateway for Puerto Rico, while Punta Cana (PUJ-Punta Cana Intl.) serves the popular resort areas of the Dominican Republic. Montego Bay (MBJ-Sir Donald Sangster Intl.) is the main airport for travelers heading to Jamaica.
What are the top things to do across the destinations in the Caribbean?
A Caribbean vacation offers a diverse range of activities across its many islands and coastal cities, each with its own unique appeal:

Browse and book things to do in the Caribbean on Expedia.
Which destinations in the Caribbean have all-inclusive resorts?
You'll find all-inclusive resorts in the Caribbean across several popular destinations, which you can book as part of a Caribbean vacation package:

Browse all-inclusive resorts in the Caribbean on Expedia.
Are there family vacation packages in the Caribbean with kid-friendly amenities?
Yes, family vacation packages in the Caribbean often feature resorts with a range of kid-friendly amenities across destinations like Punta Cana, San Juan, Noord, Montego Bay, and St. Thomas:
  • Nickelodeon Hotels & Resorts Punta Cana, Gourmet All Inclusive by Karisma: In Punta Cana, this 5-star resort offers a kids club and babysitting services, with travelers highlighting the attentive staff and so much fun at the pool.
  • Caribe Hilton: In San Juan, this 4.5-star property, rated 8 out of 10 by travelers, features a playground and game room, and travelers praise its super kid-friendly atmosphere and excellent location.
  • Embassy Suites By Hilton Aruba Beach Resort: In Noord, this 4-star resort, rated 8.7 out of 10 by travelers, provides family rooms and a kids club, with travelers frequently highlighting its top-notch breakfast and modern feel.
  • Half Moon: In Montego Bay, this 5-star resort, rated 9.1 out of 10 by travelers, features a kids club and game room, and travelers often praise its excellent food and attentive staff.
  • The Ritz-Carlton, St. Thomas: In St. Thomas, this 5-star resort, rated 7.5 out of 10 by travelers, offers a kids club and game room, with travelers frequently mentioning the amazing staff and good food.
What luxury vacation packages are available in the Caribbean?
Luxury Caribbean vacation packages can be found across several of its stunning destinations, offering premium stays and amenities:

Review the hotel included in each Caribbean vacation package. Browse luxury vacation packages in the Caribbean on Expedia to compare options.
Which destinations in the Caribbean have adults-only resorts?
Several destinations in the Caribbean offer adults-only resorts that can be booked as part of a Caribbean vacation package:

Browse adults-only resorts in the Caribbean on Expedia to compare.
When should I book vacation packages for the top destinations in the Caribbean?
For a Caribbean vacation package, most travelers book around 5 to 8 weeks ahead, depending on the destination.

Travelers tend to book Caribbean trips most often in March, from June to August, and from October to November. If you're planning a spontaneous getaway, Expedia also offers last-minute Caribbean vacation packages.
How many days do you need for a Caribbean vacation?
Most Caribbean vacation packages last around 4 to 5 days, but the ideal trip length depends on where you're going and what you'd like to experience.

Punta Cana, primarily known for its beaches and outdoor activities, is typically a 5-day trip. While some travelers opt for weekend or two-week stays, week-long trips are the most popular choice here, allowing time to enjoy attractions like Punta Cana Beach.

San Juan, a vibrant city with beaches and urban attractions, is often a 4-day trip. Most travelers choose week-long stays, though weekend trips are also common, providing enough time to explore areas like Condado Beach.

Montego Bay, a destination known for its beaches and family-friendly attractions, is typically a 4-day trip. Week-long stays are the most popular, with some travelers also choosing weekend trips, offering ample time to relax at places like Doctor's Cave Beach.
Can I change or cancel my Caribbean vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Caribbean vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Caribbean vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Caribbean vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Caribbean?
To find last-minute vacation packages to Caribbean, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Caribbean vacation packages?
Free cancellation on a Caribbean vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Caribbean vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Caribbean getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Caribbean vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.