Caribbean Vacations & Trips from ￥215,174

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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.
The Tryst Beachfront Hotel

The Tryst Beachfront Hotel

3.5 out of 5
Condado
Price was ￥278,912, price is now ￥215,174 per person
￥215,174
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
8.2/10 Very Good! (581 reviews)
Nice vibe, fantastic location, and super friendly staff! Also, the beach chairs, umbrellas and towels are all included! However, the rooms could be a bit cleaner (room floor, couch, etc.), and bathrooms really need a shelf and some hooks, because there is no place to put one's toiletries.

Reviewed on Nov 25, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Save 100% on your flight
Price was ￥587,703, price is now ￥351,297 per person
￥351,297
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
Excellent, was a wonderfull stay

Reviewed on Nov 15, 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was ￥588,416, price is now ￥387,152 per person
￥387,152
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
The room was spotless and the staff were very attentive.

Reviewed on Nov 22, 2025

El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
Old San Juan
Price was ￥302,436, price is now ￥226,862 per person
￥226,862
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9.4/10 Exceptional! (1,399 reviews)
Enjoyed my stay, very friendly staff. Big shout out to Tatiana & Christian for all the recommendations and help.

Reviewed on Nov 24, 2025

The Condado Plaza Hotel

The Condado Plaza Hotel

4 out of 5
Condado
Price was ￥383,668, price is now ￥296,391 per person
￥296,391
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
10/10 no complaints

Reviewed on Nov 26, 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
8.8/10 Excellent! (1,000 reviews)
The room was very clean staff was very friendly enjoyed my stay and will go back again 😊

Reviewed on Nov 15, 2025

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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 ￥38,520 per night from Nov 30 to Dec 1
￥38,520
￥56,265 total
Nov 30 - Dec 1
includes taxes & fees
8.6/10 Excellent! (2,043 reviews)
What stood out was the architectural structure of the hotel and how clean it was upon arrival, from the hotel grounds, lobby, restaurants, hallways, and rooms.

Reviewed on Nov 21, 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 ￥23,611 per night from Dec 16 to Dec 17
￥23,611
￥32,295 total
Dec 16 - Dec 17
includes taxes & fees
9/10 Wonderful! (1,306 reviews)
The staff were wonderful and helped us in a pinch. The room was very clean.

Reviewed on Nov 23, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 84,678 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.