Caribbean Casino Holidays 2026

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Top flight + Casino hotel deals in Caribbean

Price found within the past 48 hours. Click for updated prices.

Hotel Rumbao, a Tribute Portfolio Hotel

Old San Juan

₹65,968

per person

20 Oct - 25 Oct

found 1 day ago

Return direct flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (1,815 reviews)

Clean room Nice staff Great food Great customer service Awesome location

Reviewed on 9 Aug 2026

Majestic Elegance Punta Cana - All Inclusive

Bávaro

Save 100% on your flight

₹109,123

per person

20 Oct - 25 Oct

found 1 day ago

Return direct flight included

Toronto (YYZ) to Punta Cana (PUJ)

9/10 Wonderful! (4,936 reviews)

Me encantó todo

Reviewed on 8 Aug 2026

Barceló Bávaro Beach - Adults Only - All Inclusive

Bávaro

Save 100% on your flight

₹129,611

per person

20 Oct - 25 Oct

found 1 day ago

Return direct flight included

Toronto (YYZ) to Punta Cana (PUJ)

8.6/10 Excellent! (3,664 reviews)

The hotel room was very spacious and clean. I love that there is a balcony that you can sit in. The breakfast was very tasty and had a great variety. The staff was great.

Reviewed on 9 Aug 2026

San Juan Marriott Resort and Stellaris Casino

Condado

₹88,749

per person

20 Oct - 25 Oct

found 1 day ago

Return direct flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (1,675 reviews)

Increíble

Reviewed on 8 Aug 2026

The Condado Plaza Hotel

Condado

₹73,619

per person

20 Oct - 25 Oct

found 1 day ago

Return direct flight included

Toronto (YYZ) to San Juan (SJU)

8/10 Very good! (2,651 reviews)

Hotel is a little outdated. Only one elevator worked.

Reviewed on 9 Aug 2026

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5* Casino holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II

₹89,421

per person

20 Oct - 25 Oct

found 1 day ago

Return direct flight included

Toronto (YYZ) to San Juan (SJU)

8.6/10 Excellent! (2,188 reviews)

Horrible experience! Lazy and extremely rude staff!! Lazy cleaning staff did not clean my room 4 days!!! Extremely unprofessional!!! Reception staff extremely rude unprofessional and big liars! The reception manager is a liar! Hotel is ok, very overpriced nothing special! This is not 5 star hotel! These guys service sucks! I travel around the world! This is one of my worst experience ever!!! Terrible horrible me and my family are very disappointed won’t go back there again!!!! NEVER DONT GO

Reviewed on 8 Aug 2026

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Top Casino Caribbean Hotels

San Juan Marriott Resort and Stellaris Casino

1309 Ashford Avenue San Juan

₹25,006

₹34,626 total

7 Sept - 8 Sept

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. ...

9/10 Wonderful! (1,668 reviews)

"Increíble"

Reviewed on 8 Aug 2026

Embassy Suites by Hilton San Juan Hotel & Casino

8000 Tartak Street Carolina

₹13,634

₹20,417 total

30 Aug - 31 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. ...

Four Points by Sheraton Caguas Real Hotel & Casino

500 Alhambra En Granada Boulevard Caguas

₹19,356

₹25,137 total

18 Aug - 19 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 ...

8.8/10 Excellent! (1,005 reviews)

"Espectacular tranquilo accesible tiene lo necesario desde un descaso hasta buena gastronomía"

Reviewed on 8 Aug 2026

See all 88,662 properties in Caribbean

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.