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
Price was CA $2,069, price is now CA $1,032 per person
CA $1,032
per person
Apr 9 - Apr 13
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!
Reviewed on Feb 6, 2026
Hotel Riu Palace Antillas - Adults Only - All Inclusive
Palm Beach
Price was CA $6,060, price is now CA $3,696 per person
CA $3,696
per person
Mar 8 - Mar 13
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oranjestad (AUA)
8.6/10 Excellent! (1,420 reviews)
Friendly and helpful staff
Reviewed on Feb 5, 2026
Excellence Punta Cana - Adults Only All Inclusive
Uvero Alto
Price was CA $2,934, price is now CA $1,823 per person
CA $1,823
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Punta Cana (PUJ)
9.2/10 Wonderful! (2,456 reviews)
Room was clean, the staff amazing… the layout was nice and relaxed, perfect for those needing wheelchair accessibility. The food and spa are about a 6/10 each. The beach is wildly dangerous with strong waves even on a nice day. Lots of pros and cons. It’s a very relaxed atmosphere.
Reviewed on Feb 4, 2026
Majestic Colonial Punta Cana - All Inclusive
Bávaro
Price was CA $2,326, price is now CA $1,596 per person
CA $1,596
per person
Mar 8 - Mar 11
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Punta Cana (PUJ)
9/10 Wonderful! (6,377 reviews)
The Room and the Resort were beautiful, however, all the workers there were not very welcoming or ignored us all together. The food at the buffet was always cold, not very tasty at all. The meats were dry not much flavor. I guess my amazing trip to Cancun Mexico will remain my favorite.
Reviewed on Feb 5, 2026
The Condado Plaza Hotel
Condado
Price was CA $1,735, price is now CA $1,201 per person
CA $1,201
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
out dated for the price re: the lighting electrical outlets tv furniture. bathroom fan,safe,didnt work shower handle falls off coffee shop and bar slow service over crowded no formal resturant in the resturant had to go across the street for meals. no free water or coffee in lobby. staff was great very helpful and friendly
Reviewed on Feb 6, 2026
5* Casino holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Grand Bavaro Princess - All Inclusive
Bávaro
Price was CA $1,841, price is now CA $1,337 per person
CA $1,337
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Punta Cana (PUJ)
8.2/10 Very Good! (3,836 reviews)
Room had not pillow and blankets for the 3rd person. Very damp. Bed sheets felt humid and towels wouldn't dry. Musty smell in the room. 2 people out of 3 were sick on the third day. Ground, beach and ocean were very nice and staff are very helpful and polite.
Reviewed on Feb 5, 2026
Excellence Punta Cana - Adults Only All Inclusive
Uvero Alto
Price was CA $2,934, price is now CA $1,823 per person
CA $1,823
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Punta Cana (PUJ)
9.2/10 Wonderful! (2,456 reviews)
Room was clean, the staff amazing… the layout was nice and relaxed, perfect for those needing wheelchair accessibility. The food and spa are about a 6/10 each. The beach is wildly dangerous with strong waves even on a nice day. Lots of pros and cons. It’s a very relaxed atmosphere.
Reviewed on Feb 4, 2026
Zoetry Curaçao Resort & Spa - All Inclusive
Piscadera
Price was CA $3,706, price is now CA $2,694 per person
CA $2,694
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Willemstad (CUR)
8.4/10 Very Good! (255 reviews)
Staff was amazing. They made you feel as if you were family. We were certainly sad to leave everyone
Having access to the other hotel properties was great giving you lots of options and the beach is fantastic
Reviewed on Jan 25, 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
Price was CA $1,646, price is now CA $891 per person
CA $891
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!
Reviewed on Feb 6, 2026
Excellence Punta Cana - Adults Only All Inclusive
Uvero Alto
Price was CA $2,934, price is now CA $1,823 per person
CA $1,823
per person
Mar 8 - Mar 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Punta Cana (PUJ)
9.2/10 Wonderful! (2,456 reviews)
Room was clean, the staff amazing… the layout was nice and relaxed, perfect for those needing wheelchair accessibility. The food and spa are about a 6/10 each. The beach is wildly dangerous with strong waves even on a nice day. Lots of pros and cons. It’s a very relaxed atmosphere.
Reviewed on Feb 4, 2026
Hotel Riu Palace Antillas - Adults Only - All Inclusive
Palm Beach
Price was CA $3,478, price is now CA $2,341 per person
CA $2,341
per person
Mar 15 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oranjestad (AUA)
8.6/10 Excellent! (1,420 reviews)
Friendly and helpful staff
Reviewed on Feb 5, 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
Price was CA $2,069, price is now CA $1,032 per person
CA $1,032
per person
Apr 9 - Apr 13
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!
Reviewed on Feb 6, 2026
Majestic Elegance Punta Cana - All Inclusive
Bávaro
Price was CA $2,585, price is now CA $1,467 per person
CA $1,467
per person
Apr 8 - Apr 12
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Punta Cana (PUJ)
9/10 Wonderful! (4,541 reviews)
The resort was perfect! The staff were great and I stay in the perfect room. I am looking forward to going back.
Reviewed on Feb 6, 2026
Excellence Punta Cana - Adults Only All Inclusive
Uvero Alto
Price was CA $3,672, price is now CA $2,196 per person
CA $2,196
per person
Mar 8 - Mar 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Punta Cana (PUJ)
9.2/10 Wonderful! (2,456 reviews)
Room was clean, the staff amazing… the layout was nice and relaxed, perfect for those needing wheelchair accessibility. The food and spa are about a 6/10 each. The beach is wildly dangerous with strong waves even on a nice day. Lots of pros and cons. It’s a very relaxed atmosphere.
Reviewed on Feb 4, 2026
Casino Hotels in Caribbean
San Juan Marriott Resort and Stellaris Casino
1309 Ashford Avenue San Juan
The price is CA $739 per night from Mar 9 to Mar 10
CA $739
CA $919 total
Mar 9 - Mar 10
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! (1,514 reviews)
The room was very clean and comfortable, the entire staff was very friendly and answered every question I asked them.
Reviewed on Jan 29, 2026
Embassy Suites by Hilton San Juan Hotel & Casino
8000 Tartak Street Carolina
The price is CA $437 per night from Mar 2 to Mar 3
CA $437
CA $554 total
Mar 2 - Mar 3
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! (4,394 reviews)
Clean friendly staff
Reviewed on Feb 3, 2026
Four Points by Sheraton Caguas Real Hotel & Casino
500 Alhambra En Granada Boulevard Caguas
The price is CA $364 per night from Feb 23 to Feb 24
CA $364
CA $472 total
Feb 23 - Feb 24
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 ...
8.6/10 Excellent! (1,000 reviews)
N/A
Reviewed on Dec 27, 2025
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
