Caribbean Vacations & Trips from ￥280,928

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Top destinations in Caribbean

Dominican Republic which includes a sunset and general coastal views
FlightsFlightsHotelsHotels

Santo Domingo

Santo Domingo

The Latest Caribbean Vacation Packages

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

Brickell Apart Hotel

5 out of 5
Bella Vista
per person
Aug 21 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Santo Domingo (SDQ)
8.8/10 Excellent! (165 reviews)
Very convenient location.

Reviewed on Jul 2, 2025

Hodelpa Nicolas de Ovando

Hodelpa Nicolas de Ovando

4.5 out of 5
Zona Colonial
per person
Aug 21 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Santo Domingo (SDQ)
9.2/10 Wonderful! (1,003 reviews)
Loved the historical roots

Reviewed on Jun 28, 2025

Dominican Fiesta Hotel

Dominican Fiesta Hotel

4 out of 5
Los Cacicazgos
per person
Aug 21 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Santo Domingo (SDQ)
8/10 Very Good! (2,338 reviews)
Todo estaba muy bien, creo que deberian mejorar el baño, estaba muy viejo e incomodo de bañarse

Reviewed on Jul 6, 2025

W&P Santo Domingo

W&P Santo Domingo

4 out of 5
Bella Vista
per person
Aug 21 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Santo Domingo (SDQ)
9/10 Wonderful! (1,001 reviews)
Excellent will definitely be back

Reviewed on Jul 5, 2025

Luca Hotel by Heritage Residences Signature Collection

Luca Hotel by Heritage Residences Signature Collection

3.5 out of 5
Zona Colonial
per person
Aug 21 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Santo Domingo (SDQ)
9.2/10 Wonderful! (644 reviews)
Room is really nice. There is no onsite parking like it says. Jacuzzi was broken when we were there. There is street parking and it’s first come first serve to the public.

Reviewed on Jul 3, 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! (1,001 reviews)
"Excellent location."

Reviewed on Jun 28, 2025

Get rates
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 ￥30,710 per night from Jul 7 to Jul 8
￥30,710
￥45,845 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (1,724 reviews)
"Nice"

Reviewed on Jul 3, 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 ￥27,384 per night from Aug 4 to Aug 5
￥27,384
￥35,361 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"We love the location, we got two rooms with balcony one, the door opened to see outside which it was wonderful, the other one was broken, we arrived late and missed to call maintenance to get it repaired. The staff was very nice and professional, we walked to restaurants and saw cruise ships arriving ..."

Reviewed on Jul 5, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 80,862 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.