Caribbean Casino Vacations

Book a Casino Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ¥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Casino vacation packages in Caribbean

Price found within the past 48 hours. Click for updated prices.
Hotel Rumbao, a Tribute Portfolio Hotel
The Royal Sonesta San Juan
The Condado Plaza Hotel
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Courtyard by Marriott Isla Verde Beach Resort
Don't see what you're looking for?
See all available trips from Ontario to Caribbean
View all trips

5* Casino vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Hard Rock Hotel & Casino Punta Cana an All-Inclusive Resort
Sonesta Ocean Point All Inclusive, Adults Only Resort
Don't see what you're looking for?
See all available trips from Ontario to Caribbean
View all trips

3 Night Casino vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.
Barceló Bávaro Beach - Adults Only - All Inclusive
Hard Rock Hotel & Casino Punta Cana an All-Inclusive Resort
Barceló Bávaro Palace - All Inclusive
Don't see what you're looking for?
See all available trips from Tokyo to Caribbean
View all trips

4 Night Casino vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.
The Condado Plaza Hotel
The Royal Sonesta San Juan
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Don't see what you're looking for?
See all available trips from Ontario to Caribbean
View all trips

Top Casino Caribbean Hotels

San Juan Marriott Resort and Stellaris Casino

San Juan Marriott Resort and Stellaris Casino

4.5 out of 5
1309 Ashford Avenue, San Juan
The price is ¥43,547 per night from Aug 18 to Aug 19
¥43,547
¥58,948 total
Aug 18 - Aug 19
includes taxes & fees
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,305 reviews)
"Beautiful property and very well kept, clean and safe. Beautiful views, great food, drinks and pools! Truly enjoyed our stay and cannot wait to plan our next returning visit! 100% recommend!"

Reviewed on Jul 24, 2025

San Juan Marriott Resort and Stellaris Casino
Embassy Suites by Hilton San Juan Hotel & Casino

Embassy Suites by Hilton San Juan Hotel & Casino

3.5 out of 5
8000 Tartak Street, Carolina
The price is ¥23,315 per night from Aug 11 to Aug 12
¥23,315
¥32,470 total
Aug 11 - Aug 12
includes taxes & fees
Stay at this 3.5-star family-friendly resort in Carolina. Enjoy free breakfast, free WiFi, and a casino. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (3,715 reviews)
"Amazing and just what we needed. A perfect getaway close to the beach and also a wonderful pool, breakfast, and more."

Reviewed on Jul 23, 2025

Embassy Suites by Hilton San Juan Hotel & Casino
Sheraton Puerto Rico Resort & Casino

Sheraton Puerto Rico Resort & Casino

4 out of 5
200 Convention Boulevard, San Juan
The price is ¥32,958 per night from Aug 25 to Aug 26
¥32,958
¥45,562 total
Aug 25 - Aug 26
includes taxes & fees
Stay at this 4-star spa hotel in San Juan. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,009 reviews)
"The Sheraton in San Juan is a lovely property."

Reviewed on Jul 21, 2025

Sheraton Puerto Rico Resort & Casino
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.