Caribbean Vacations & Trips from $354

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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

Condado Beach which includes general coastal views and a coastal town
FlightsFlightsHotelsHotels

San Juan

San Juan

The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
9/10 Wonderful! (453 reviews)
I had a fantastic stay at this hotel! The staff were incredibly welcoming and helpful from the moment we arrived. Our room was spotless, comfortable, and well-equipped with everything we needed. The location was perfect, close to local attractions but still quiet and relaxing. I especially enjoyed the breakfast each morning, a great way to start the day. I would definitely stay here again and highly recommend it to anyone visiting the area!

Reviewed on Aug 8, 2025

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.8/10 Excellent! (441 reviews)
Swim out is the way to go the gym was top notch and The Reef was one of the hidden gem lunch spots. There was always something to do and the MJ show was great!

Reviewed on Aug 8, 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9.2/10 Wonderful! (300 reviews)
Very beautiful resort. However, food and entertainment options are subpar at best. I was unfortunately disappointed. Nadia in the spa is THE BEST! If you stay here, get the platinum club, that’s where the food is good.

Reviewed on Aug 8, 2025

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nassau (NAS)
8/10 Very Good! (3,126 reviews)
I’ve stayed here twice before. Once before COVID (2019) and the second time in 2025. I’ll admit the first time I stayed I had no issues but I was doing a lot of excursions and not at the resort 24/7. This second time around, I wanted a chill vacation where I could rot on the beach and I was able to get that but I noticed a lot more. The rooms are very outdated and are filled with ants. The food isn’t really bad but it’s not great either (even if you book at one of their restaurants). I did see a specific type of bug (I think y’all know what kind I'm talking about) that was crawling around in the buffet area. Overall I think it’s just a very outdated hotel (can’t even call it a resort because it’s so small) and I personally think that RIU should update this specific location. Most RIU branches are a hit or miss and this was a miss for me. However, I do want to mention that the staff is super friendly and accommodating which I really appreciate and they try to do a lot of day time activities to keep the energy up which I also like. If you’re looking for a place just to sleep and want to eat and drink anything and everything, this probably would be a great option. But if you want to stay on the resort property and rot on a beach (which I will also admit was beautiful and well kept) like me then I would say to look elsewhere.

Reviewed on Aug 8, 2025

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Oct 12 - Oct 16
found 13 hours ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)

Best Places to Vacation 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.

Find the Best Caribbean Vacation Packages

Things to do in Caribbean

Discover the Caribbean's vibrant culture through exciting festivals, wellness retreats, and breathtaking scenic parks. Engage in various activities such as hiking along stunning trails and enjoying the local cuisine. Whether you're seeking relaxation or adventure, the Caribbean offers a perfect blend of experiences that cater to every traveler's interests, ensuring an unforgettable vacation filled with natural beauty and cultural richness.

Shopping

Renaissance Mall Aruba offers a vibrant shopping experience with entertainment and family-friendly vibes, perfect for finding gifts. For a unique twist, visit the Straw Market, where you can discover local crafts and souvenirs in a bustling atmosphere.

Recreation

El Conquistador Golf Course offers stunning views and a challenging layout for golf enthusiasts, perfect for outdoor recreation. Scape Park is a tranquil oasis, featuring rejuvenating wellness activities amidst lush landscapes. National Stadium hosts energetic sports events, making it an exciting venue for sports lovers looking for vibrant activities.

Adventure

Experience thrilling water slides and wave pools at Sirenis Aquagames Water Park, perfect for family fun. Soar through the treetops at Mystic Mountain, embracing pure adventure. Take in breathtaking views from the Puerto Plata Cable Car, an outdoor experience that the whole family will cherish.

Nightlife

Experience the vibrant nightlife in the Caribbean at Coco Bongo Punta Cana, where romance and entertainment blend in a lively atmosphere. For a laid-back vibe, visit Floyd's Pelican Bar or Magic Ice Gallery for drinks, laughter, and unforgettable moments under the stars.

*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 breathtaking destination featuring stunning beaches, serene bays, and historic churches. It offers a rich blend of culture and outdoor experiences for travelers. Popular attractions include beautiful shorelines and cultural sites that cater to diverse interests. To enhance your visit, consider looking into various Caribbean destinations and vacation packages that can help you explore this tropical paradise effortlessly.

  • Eagle Beach: This stunning beach is renowned for its soft white sands and crystal-clear waters, making it perfect for sunbathing and relaxation. The laid-back atmosphere allows you to soak in the sun while enjoying beach activities such as swimming and beach volleyball. The picturesque landscape offers breathtaking sunset views, creating a tranquil escape.
  • El Yunque National Forest: Immerse yourself in this lush rainforest, where vibrant flora and fauna abound. Experience eco-friendly outdoor adventures, including hiking trails that lead to stunning waterfalls and panoramic vistas. The diverse scenery is perfect for nature lovers and offers a serene retreat from the hustle and bustle.
  • Magens Bay Beach: Known for its stunning bay views and gentle waves, this beach is ideal for swimming, kayaking, or simply lounging under the sun. With its surrounding lush hills and vibrant scenery, Magens Bay provides a picturesque setting for a perfect beach day, making it a must-visit destination.

Best time to go to Caribbean

The best time to visit Caribbean is dependant on what kind of holiday you are seeking. September is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. November is its coolest month on average. At this time, 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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Caribbean.
  • Consider traveling during the off-peak season (typically September to November) for more affordable package holidays to Caribbean.
  • 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

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
$243 nightly
The price is $265 total per night from Sep 8 to Sep 9
$265 total
Sep 8 - Sep 9
Total includes taxes and 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
$228 nightly
The price is $250 total per night from Aug 31 to Sep 1
$250 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (1,855 reviews)
"The service, always top notch, best bar staff in Nassau,my boy Omar always on point"

Reviewed on Aug 7, 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
$204 nightly
The price is $222 total per night from Sep 9 to Sep 10
$222 total
Sep 9 - Sep 10
Total includes taxes and fees
9/10 Wonderful! (1,080 reviews)
"Excellent!"

Reviewed on Aug 7, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
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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.
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Frequently asked questions

How much does a Caribbean vacation package cost?
Custom make your Caribbean vacation package from only $354. Choose from any combination of rental cars, flights and hotels to create the getaway you've been dreaming about. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Caribbean?
Search for flights that suit your busy schedule, add a hotel room to your booking and watch the savings pile up with a Caribbean vacation package. It's that simple! From hotels and flights to activities and rental cars, Expedia makes traveling on a budget easy. And with more than 550 air carriers and 1,000,000 hotels all over the world to pick from, you won't be short of choice.
How far in advance should I book my Caribbean vacation?
While not all air carriers advertise ticket prices early, customers are usually able to start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic deals. If you're booking late, you may still be in luck. Sometimes the lowest prices emerge just weeks prior to departure.
What does an Expedia Caribbean travel package include?
It comes down to what you're looking for. If you're traveling alone, you might decide to combine hotels and flights. Taking the entire family to Caribbean? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the freedom and flexibility to build your own travel package.
What should I know before booking a Caribbean travel package?
Get set to save with an Expedia travel package. Combine your airfares, rental cars and hotels and enjoy fantastic discounts. You're not restricted to hotels, however. We have beachside condos, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a Caribbean Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
Does Expedia offer Book Now, Pay Later Caribbean vacation packages?
Your bank balance shouldn't stop you from having a fabulous vacation, so Expedia has devised a solution to help. Thanks to our partnership with online lender Affirm, it's easier than ever to book an amazing getaway that won't hurt your savings. Simply Book Now, Pay Later and take the financial stress out of planning for your journey.
If I'm not able to travel, can I cancel my Caribbean vacation package?
Certainly, and we're here to help. You may be able to cancel or change your Caribbean vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, browse our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.