Caribbean Vacations & Trips from ￥142,486

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Top destinations in Caribbean

Bayahibe Beach featuring general coastal views
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Punta Cana

Punta Cana

The Latest Caribbean Vacation Packages

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

Urbana Hotel

2 out of 5
San Juan Antiguo
Price was ￥208,614, price is now ￥142,486 per person
￥142,486
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
8.6/10 Excellent! (368 reviews)
Yes on both accounts. If guests ask for a place to eat the staff should recommend the Thai restaurant 3/10 of a mile away. Easy walk and most importantly excellent food at good prices and the staff was amazing!!!

Reviewed on Nov 12, 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Price was ￥261,462, price is now ￥164,150 per person
￥164,150
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9.2/10 Wonderful! (542 reviews)
New mattress is a priority! The one we slept on was sinking in the middle. Very uncomfortable!!! Other than that it was a very good stay. The people who work there are very nice. Very clean.

Reviewed on Nov 10, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Save 100% on your flight
Price was ￥365,781, price is now ￥244,134 per person
￥244,134
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
8.6/10 Excellent! (563 reviews)
Amazing location , helpful attentive kind staff , unique vibes definitely would recommend

Reviewed on Oct 30, 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was ￥351,820, price is now ￥240,842 per person
￥240,842
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9/10 Wonderful! (290 reviews)
Everything great. The only bad thing was the housekeeping knocking the door very early in the morning.

Reviewed on Nov 10, 2025

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

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

4 out of 5
Condado
Save 100% on your flight
Price was ￥373,952, price is now ￥260,879 per person
￥260,879
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9/10 Wonderful! (643 reviews)
Beautiful hotel, amazing staff

Reviewed on Oct 30, 2025

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 ￥68,556 per night from Dec 4 to Dec 5
￥68,556
￥89,671 total
Dec 4 - Dec 5
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
A wonderful stay at this beautiful and authentic hotel. What a great location with lots of cafés and restaurants in all directions. All staff were superb. The pool and terrace were very nice.

Reviewed on Nov 8, 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
The price is ￥34,346 per night from Nov 27 to Nov 28
￥34,346
￥50,934 total
Nov 27 - Nov 28
includes taxes & fees
8.6/10 Excellent! (2,019 reviews)
11 nights - King room with private terrace - Front desk staff handled a misrepresentation of our room book through Expedia effectively, taking ownership of the issue. Clean private beach, attentive courteous staff, excellent hospitality and housekeeping service.

Reviewed on Nov 8, 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
The price is ￥22,678 per night from Dec 8 to Dec 9
￥22,678
￥31,190 total
Dec 8 - Dec 9
includes taxes & fees
9/10 Wonderful! (1,264 reviews)
Excellent staff, good amenities, clean room.

Reviewed on Nov 9, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 84,638 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.