Roosevelt Roads Cheap Vacations
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Flight and Cheap hotel deals in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes
Puerta de Tierra
Price was CA $2,952, price is now CA $1,740 per person
CA $1,740
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (755 reviews)
Staff was excellent and very helpful during our stay especially Hector. Unfortunately the shuttle has been out of service and the hot tub needed cleaning. There were several other issues we encountered that were rectified by the Hector as well as other staff members at the time of need.
Reviewed on Nov 7, 2026
WALD HAUS by DW
Price was CA $5,427, price is now CA $3,591 per person
CA $3,591
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (11 reviews)
The home itself is absolutely stunning but the road to the villa is not just narrow, it's washed out in many places, we struggled to navigate the potholes even with a jeep and an SUV, I would not drive it at night. There are great amenities like the fridge and bathroom downstairs, the coffee / cocktail bar is fabulous.The kitchen was well-stocked with basic spices and supplies but it was crawling with roaches. Wifi is spotty so be sure to have the guidebook downloaded and screenshots of the phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.
Reviewed on Aug 13, 2026
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Price found within the past 48 hours. Click for updated prices.
Residences at Dorado Beach, a Ritz-Carlton Reserve
Higuillar
Price was CA $43,269, price is now CA $34,323 per person
CA $34,323
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans.
Reviewed on Sep 1, 2025
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DoubleTree by Hilton San Juan
Santurce
Price was CA $1,566, price is now CA $1,288 per person
CA $1,288
per person
Jan 14 - Jan 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
9/10 Wonderful! (1,006 reviews)
The hotel nice and clean. The pool nice. The neighborhood nice with 24 hour supermarket across the street. The only thing I did not like was breakfast was not included in my package and not sure why. So when booking make sure breakfast is included in your package however overall I give it a 10. Thank you.
Reviewed on Nov 5, 2026
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