Luxury Holidays in Caribbean Islands 2026

Plan, book, travel with confidence
Better together
Save up to HK$7,200 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

Condado Vanderbilt Hotel

1055 Ashford Avenue San Juan

7 hours drive from Oyster Bay Marina

Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Salt Coppers Runaway Bay Saint Ann

32 hours drive from Oyster Bay Marina

Stay at this luxury resort in Runaway Bay. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. ...

8.4/10 Very good! (2,492 reviews)

"Pro: Beautiful hotel right on the beach. Beautiful pool and grounds. Food was delicious with great variety. My room was clean and spacious. The staff were helpful, friendly and professional. Con: the hotel gift shop charges US$20 for a bottle of 16 ounces GATORADE!!! Even though it is an all inclusive ..."

Reviewed on 14 Sept 2026

Hotel El Convento

100 Cristo St San Juan

7 hours drive from Oyster Bay Marina

Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean rooms in their ...

9.2/10 Wonderful! (1,005 reviews)

"The beautiful building and historic structure"

Reviewed on 13 Sept 2026

See all 88,891 properties in Caribbean Islands

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.