Caribbean Casino Holidays
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- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
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Top flight + Casino hotel deals in Caribbean
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
Price was AU$2,272, price is now AU$1,246 per person
AU$1,246
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,887 reviews)
Pleasant stay
Reviewed on 21 July 2026
5* Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
4 Night Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
Price was AU$2,272, price is now AU$1,246 per person
AU$1,246
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,887 reviews)
Pleasant stay
Reviewed on 21 July 2026
Top Casino Caribbean Hotels
San Juan Marriott Resort and Stellaris Casino
1309 Ashford Avenue San Juan
The price is AU$688 per night from 18 Aug to 19 Aug
AU$688
18 Aug - 19 Aug
includes taxes & fees
Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, 2 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
Embassy Suites by Hilton San Juan Hotel & Casino
8000 Tartak Street Carolina
The price is AU$443 per night from 16 Aug to 17 Aug
AU$443
16 Aug - 17 Aug
includes taxes & fees
Stay at this family-friendly resort in Carolina. Enjoy free breakfast, free Wi-Fi and a casino. Our guests praise the breakfast and the pool in their reviews. ...
9/10 Wonderful! (4,788 reviews)
"The hotel show s signs of water damage on the upper floor walk way, the pool was nice but once you go under water there was lots of debris and trash on the bottom. Also I was charged a fundraising campaign fee that I did not approve. I called the hotel and was directed to accounting, no one answered ..."
Reviewed on 21 July 2026
Four Points by Sheraton Caguas Real Hotel & Casino
500 Alhambra En Granada Boulevard Caguas
The price is AU$377 per night from 5 Aug to 6 Aug
AU$377
5 Aug - 6 Aug
includes taxes & fees
Stay at this golf hotel in Caguas. Enjoy free Wi-Fi, a casino and breakfast (surcharge). Our guests praise the helpful staff in their 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
