Caribbean Casino Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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 $737
per person
Oct 26 - Oct 29
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
It was central and very close by to everything. Staff were friendly , views were amazing .
Reviewed on Sep 24, 2026
5* Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
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 $737
per person
Oct 26 - Oct 29
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
It was central and very close by to everything. Staff were friendly , views were amazing .
Reviewed on Sep 24, 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 $1,173
per person
Nov 1 - Nov 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
It was central and very close by to everything. Staff were friendly , views were amazing .
Reviewed on Sep 24, 2026
Casino Hotels in Caribbean
San Juan Marriott Resort and Stellaris Casino
1309 Ashford Avenue San Juan
CA $370
CA $513 total
Sep 29 - Sep 30
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 ...
9/10 Wonderful! (1,746 reviews)
"We absolutely loved our stay! The hotel was absolutely beautiful, and the staff was so kind and welcoming. Everything was wonderful from start to finish. We would definitely stay here again! ❤️"
Reviewed on Sep 24, 2026
Embassy Suites by Hilton San Juan Hotel & Casino
8000 Tartak Street Carolina
CA $224
CA $327 total
Oct 1 - Oct 2
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! (4,969 reviews)
"Place clean , staffs cool, breakfast was great and a lot of options. Only problem I had was the places for food closes pretty early"
Reviewed on Sep 23, 2026
Four Points by Sheraton Caguas Real Hotel & Casino
500 Alhambra En Granada Boulevard Caguas
CA $256
CA $333 total
Oct 4 - Oct 5
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 ...
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.
