
Caribbean Holidays
Better together
Save up to S$134 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top destinations in Caribbean

Santo Domingo
Top hotels in Caribbean

Hotel El Convento
100 Cristo St, San Juan
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,002 reviews)
"The property was great. I liked everything about the hotel"
Reviewed on 10 Jul, 2025

British Colonial - Nassau
Number One Bay St, Nassau
Fully refundableReserve now, pay when you stay
The price is S$443 per night from 21 Jul to 22 Jul
S$443
21 Jul - 22 Jul
includes taxes & fees
8.6/10 Excellent! (1,738 reviews)
"Excellent property"
Reviewed on 10 Jul, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street, San Juan, Puerto Rico
Fully refundableReserve now, pay when you stay
The price is S$313 per night from 4 Aug to 5 Aug
S$313
4 Aug - 5 Aug
includes taxes & fees
9/10 Wonderful! (1,021 reviews)
"Very quite, closed to old San Juan and service was good."
Reviewed on 11 Jul, 2025
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.
More trip options
Expedia's Latest Trends
Hotels
- Hotels with Yoga in Dominican Republic
- Hotels with smoking rooms in Antigua and Barbuda
- Hotels with Airport Shuttle in Santo Domingo
- Hotels with Yoga in Turks and Caicos
- Hotels with smoking rooms in Aruba
- Hotels with smoking rooms in Barbados
- Hotels with smoking rooms in Curaçao
- Sister Islands hotels
- Hotels with Early Check In in Trinidad and Tobago
Flights
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.