Caribbean Casino Vacations
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Flight and Casino hotel deals in Caribbean
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $910
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Very clean rooms and friendly staff. Balcony view was beautiful and could see the beach. Property is walking distance to a lot of popular attractions and restaurants
Reviewed on Aug 9, 2026
Hotel Riu Palace Antillas - Adults Only - All Inclusive
Palm Beach
CA $2,783
per person
Sep 8 - Sep 13
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Oranjestad (AUA)
8.6/10 Excellent! (1,700 reviews)
The room was always clean and updated, but the USB port next to the bed did not work, and there was no other outlet next to the bed for usage. Also the hallway smelled of must and water. The hallways and lobby need updating. The swim up bar pool was absolutely disgusting. Slimey and dirty water. Palace pool was MUCH better. 10/10 for the palace pool and grounds. Breakfast and lunch 10/10 but there needs to be more dinner options. Steak house maxing out at 6pm in unacceptable. Overall experience was a 6/10. I would stay at the palace side next time.
Reviewed on Aug 9, 2026
5* Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Grand Bavaro Princess - All Inclusive
Bávaro
CA $966
per person
Sep 9 - Sep 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Punta Cana (PUJ)
8.2/10 Very good! (4,152 reviews)
Had a great time overall here: loved how clean the room and property was, friendly bartenders at the pool bar, loved foam party and karaoke at the pub!
Few things that could be better: food especially at ala- karte restaurants, evening show at the theater was too hot, some waiters in the lobby bar were not helpful or would just pass by kind of ignoring you, and the alcohol felt like a lemonade overall 🙂
Reviewed on Aug 9, 2026
3 Night Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $910
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Very clean rooms and friendly staff. Balcony view was beautiful and could see the beach. Property is walking distance to a lot of popular attractions and restaurants
Reviewed on Aug 9, 2026
4 Night Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $936
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Very clean rooms and friendly staff. Balcony view was beautiful and could see the beach. Property is walking distance to a lot of popular attractions and restaurants
Reviewed on Aug 9, 2026
Casino Hotels in Caribbean
San Juan Marriott Resort and Stellaris Casino
1309 Ashford Avenue San Juan
CA $366
CA $507 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this 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 our ...
Embassy Suites by Hilton San Juan Hotel & Casino
8000 Tartak Street Carolina
CA $200
CA $299 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this family-friendly resort in Carolina. Enjoy free breakfast, free WiFi, and a casino. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (4,857 reviews)
"Excelente!"
Reviewed on Aug 9, 2026
Four Points by Sheraton Caguas Real Hotel & Casino
500 Alhambra En Granada Boulevard Caguas
CA $283
CA $368 total
Aug 22 - Aug 23
includes taxes & fees
Book a stay at this golf hotel in Caguas. Enjoy free WiFi, a casino, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,006 reviews)
"Todo exelente!"
Reviewed on Aug 9, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
