Caribbean Vacation Packages 2026 from ￥357,480

Top destinations in Caribbean

The Latest Caribbean Vacation Packages

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

Lazy Parrot Inn

￥357,480

per person

May 11 - May 16

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to San Juan (SJU)

9.2/10 Wonderful! (1,007 reviews)

Loved this room. Clean and comfortable- quiet yet accessible. Highly recommend.

Reviewed on Mar 23, 2026

Hotel Puerto Valdes

San Juan Antiguo

￥364,994

per person

May 12 - May 16

found 7 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to San Juan (SJU)

8.8/10 Excellent! (594 reviews)

Room had ample space, bed was very comfortable, appreciated the 24/7 access to coffee and filtered water. Staff was super friendly

Reviewed on Mar 25, 2026

OLV Fifty Five - Adults Only

Condado

￥393,071

per person

May 12 - May 16

found 7 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to San Juan (SJU)

8.6/10 Excellent! (622 reviews)

The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices.

Reviewed on Mar 16, 2026

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Condado

￥400,940

per person

May 12 - May 16

found 7 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to San Juan (SJU)

9/10 Wonderful! (662 reviews)

The noise is unbearable. We were on the third floor and had small windows connected a metal stairway that is so loud and it was like they were having a party up on the roof all night. We had to be up at 1am to catch a flight and couldn’t sleep at all. Between the paper thin walls where we hear everything the other rooms in our hall were doing and the loud party, we couldn’t sleep. At $500 a night this was unacceptable. The place is clean and comfortable, but you can’t relax at night with all the noise.

Reviewed on Mar 9, 2026

Hyatt Vacation Club at Hacienda del Mar, Dorado

Sabana

￥402,458

per person

May 11 - May 16

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to San Juan (SJU)

9.4/10 Exceptional! (3,304 reviews)

This is my second time staying here and loved it both times! Rooms are beautiful with gorgeous views. Staff is really friendly. The restaurant on site called Mahi Mahi is really good and reasonably priced.

Reviewed on Mar 25, 2026

Things to do in Caribbean

Shopping

Experience the vibrant shopping scene in the Caribbean at Renaissance Shopping Mall, which offers a mix of business, entertainment, and family-friendly vibes. Visit the Straw Market for a unique local atmosphere and souvenirs. For everyday needs, Mega Mart provides a convenient shopping option.

Recreation

Experience the natural beauty of Scape Park, where you can indulge in wellness activities amidst lush landscapes and serene vibes. At Coco Beach Golf and Country Club, enjoy luxury amenities and a round of golf, while Arecibo Observatory offers engaging family entertainment in a unique astronomical setting.

Adventure

Mystic Mountain offers thrilling activities like zip-lining and bobsledding through lush landscapes. Aquaventure features exhilarating water slides and lazy rivers, perfect for family fun. The Skyride to Paradise Point provides breathtaking views as you ascend, making it a delightful outdoor adventure for all ages.

Nightlife

Experience the vibrant nightlife of the Caribbean at Coco Bongo Punta Cana, where romance meets electrifying entertainment. Visit Floyd's Pelican Bar for a laid-back atmosphere and refreshing drinks. Don't miss Casa de la Musica de Centro, where city vibes and live music create an unforgettable night out.

*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 diverse array of attractions for every traveler, featuring beautiful beaches, serene bays, and historic churches. Explore vibrant cultures and enjoy outdoor experiences while discovering popular Caribbean destinations. To enhance your trip, consider looking into Caribbean vacation packages that provide unforgettable experiences tailored to your interests.

Eagle Beach: Experience the stunning beauty of Eagle Beach, known for its powdery white sand and turquoise waters. This beach offers a serene atmosphere perfect for relaxation, sunbathing, and swimming. The vibrant beach vibes create an inviting environment for both families and solo travelers.
El Yunque National Forest: Explore El Yunque, a lush rainforest teeming with diverse wildlife and breathtaking scenery. Enjoy eco-friendly adventures with hiking trails that lead to stunning waterfalls and panoramic views. It's a paradise for outdoor enthusiasts and nature lovers.
Magens Bay Beach: Discover Magens Bay Beach, famous for its tranquil waters and picturesque surroundings. Ideal for swimming and sunbathing, this bay offers a scenic backdrop for a perfect day outdoors. It’s a favorite spot for both relaxation and recreation.

Best time to go to Caribbean

The best time to visit Caribbean is dependent 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	79.3°F (26.3°C)	No Rain	Mostly Sunny	Slightly High	Average
February	78.8°F (26.0°C)	No Rain	Mostly Sunny	Average	Slightly High
March	79.2°F (26.200000000000003°C)	No Rain	Mostly Sunny	Average	Slightly High
April	80.1°F (26.700000000000003°C)	Light Rain	Mostly Sunny	Average	Average
May	80.4°F (26.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny	Average	Average
July	82.2°F (27.9°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	82.8°F (28.200000000000003°C)	Light Rain	Mostly Sunny	Average	Average
September	82.9°F (28.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	78.3°F (25.700000000000003°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	79.5°F (26.4°C)	No Rain	Mostly Sunny	Average	Slightly 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 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.

Caribbean Hotel Deals

Hotel El Convento

100 Cristo St San Juan

Fully refundableReserve now, pay when you stay

￥44,769

￥58,558 total

Apr 27 - Apr 28

includes taxes & fees

9/10 Wonderful! (1,003 reviews)

My Hotel Convento stay was comfortable and pleasant. The hotel service was excellent and staff was very helpful and friendly.The old world charm makes this hotel in comparison to other hotels in the area a must experience by all who come to Old San Juan.

Reviewed on Mar 26, 2026

British Colonial - Nassau

Number One Bay St Nassau

Fully refundableReserve now, pay when you stay

￥36,508

￥53,904 total

Apr 26 - Apr 27

includes taxes & fees

8.6/10 Excellent! (2,395 reviews)

Room location 444 was not ideal. It’s next to the elevator and you hear it moving up and down ALL night and early in the morning. Around 3:00am repairs were being done that cause a loud banging against metal sound. It last an hour. I had an early flight that morning so needless to say it was not ...

Reviewed on Mar 27, 2026

Hotel Rumbao, a Tribute Portfolio Hotel

100 Brumbaugh Street San Juan Puerto Rico

Fully refundableReserve now, pay when you stay

￥40,509

￥50,849 total

Apr 21 - Apr 22

includes taxes & fees

9/10 Wonderful! (1,589 reviews)

Great location close to the cruise port

Reviewed on Mar 25, 2026

See all 85,199 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.

Frequently asked questions

Can I travel to Caribbean right now?

For all the up-to-date facts about visiting Caribbean, take a look at our Covid-19 Travel Advisor. From quarantine policies to travel restrictions and more, Expedia will help make your trip planning as stress-free as possible.

If I'm not able to travel, can I cancel my Caribbean vacation package?

Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Caribbean vacation package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

When is the best time of year to visit Caribbean?

There's a real advantage to taking your Caribbean vacation in . You can usually pick up the best deals at this time. , on the other hand, is the most expensive time to visit. If you like the buzz of peak season, head to Caribbean in . The calmer months of will help you avoid the crowds.

How far in advance should I book my Caribbean vacation?

It all depends on the air carrier, but you can usually look up international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travelers will occasionally find a cheaper ticket only weeks before the date of departure.

What should I know before booking a Caribbean travel package?

So many places to go, so many things to see and do. With a travel package, you'll be able to afford more of them. Bundle your hotels, rental cars and flights and make big savings.

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

Caribbean Vacations & Trips from ￥357,480

Book a Hotel + Flight or Car together to unlock savings

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Top destinations in Caribbean

Punta Cana

St. Thomas

Montego Bay

Nassau

Providenciales

St. John

Oranjestad

The Latest Caribbean Vacation Packages

Lazy Parrot Inn

Hotel Puerto Valdes

OLV Fifty Five - Adults Only

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Hyatt Vacation Club at Hacienda del Mar, Dorado

Things to do in Caribbean

Find the best attractions in Caribbean

Best time to go to Caribbean

Tips to save on your trip to Caribbean

Caribbean Hotel Deals

Hotel El Convento

British Colonial - Nassau

Hotel Rumbao, a Tribute Portfolio Hotel

Frequently asked questions