Title: Roosevelt Roads Vacation Packages & Trips 2026 from CA $855 | Expedia.ca [Roosevelt Roads Travel Guide](https://expedia.ca/Roosevelt-Roads.dx6360451)[Hotels in Roosevelt Roads](https://expedia.ca/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[Vacation Rentals in Roosevelt Roads](https://expedia.ca/Roosevelt-Roads-Vacation-Rentals.d6360451.Travel-Guide-VacationRentals)[Flights to Roosevelt Roads](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[Roosevelt Roads Car Rentals](https://expedia.ca/Car-Rentals-In-Roosevelt-Roads.d6360451.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roosevelt Roads Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Shannon Willitts - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Roosevelt Roads Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $855 per person Feb 22 - Feb 27 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (500 reviews) Had to ask for facecloth and hand towel. Personnel was very useful. We could walk to the old San Juan. Reviewed on Jan 11, 2026 ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $1,438 per person Apr 2 - Apr 9 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Great! And highly recommended Reviewed on Jan 12, 2026 ![Lazy Parrot Inn](https://images.trvl-media.com/lodging/1000000/910000/900400/900306/77384e02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lazy Parrot Inn CA $921 per person Mar 2 - Mar 9 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (1,000 reviews) Great room with view of the property and sunset. The Thai restaurant was fantastic! The property was very well managed, cared for and cleaned, the grounds keeper does an amazing job. The clean pool and hot tub were winderful ways to end your day in Rincon. We'll be back! Reviewed on Jan 11, 2026 ![The Oliver Hotel](https://images.trvl-media.com/lodging/108000000/107090000/107083400/107083384/2b5683ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Oliver Hotel San Juan Antiguo CA $1,249 per person Apr 2 - Apr 9 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 9/10 Wonderful! (50 reviews) Definitely a different experience to not have a ton of amenities or staff on site at all times as they manage multiple properties. That being said, they were always a quick text or phone call away and everyone was extremely friendly and helpful. Great location and very clean room. I would definitely recommend this spot for the next traveler looking for a great (and walkable) place to stay near Old San Juan and/or Condado. Reviewed on Jan 5, 2026 ![Dorado Beach 5 Bedroom Villa](https://images.trvl-media.com/lodging/117000000/116020000/116013900/116013898/413e7713_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dorado Beach 5 Bedroom Villa Higuillar CA $3,190 per person Mar 1 - Mar 7 found 15 hours ago Roundtrip non-stop flight included Calgary (YYC) to San Juan (SJU) 10/10 Exceptional! (1 review) Space, location, private accommodations, modern kitchen, washer dryer Reviewed on Nov 27, 2025 ## Ready to book your vacation to Roosevelt Roads? Choose your dates ## Roosevelt Roads Hotel Deals ![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Grand Reserve Puerto Rico 200 Coco Beach Blvd. Highway 955-I Río Grande Fully refundableReserve now, pay when you stay CA $594 CA $764 total Jan 20 - Jan 21 includes taxes & fees 8.8/10 Excellent! (2,860 reviews) The stay was very enjoyable. Able to relax and enjoy the amenities. Service was good, everyone was friendly Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F01%2F2026&endDate=21%2F01%2F2026&selected=979694&PinnedHotelID=979694&HadPinnedHotel=true®ionId=6360451) ![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/926a31f3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### El Conquistador Resort 1000 Conquistador Avenue Fajardo Fully refundableReserve now, pay when you stay CA $437 CA $575 total Jan 19 - Jan 20 includes taxes & fees 9/10 Wonderful! (3,202 reviews) Very clean. Excellent staff. We love it Reviewed on Jan 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=447559&PinnedHotelID=447559&HadPinnedHotel=true®ionId=6360451) ![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/0558d37f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Grand Rio Mar Rainforest Beach and Golf Resort 6000 Rio Mar Boulevard Río Grande Fully refundableReserve now, pay when you stay CA $877 CA $1,206 total Feb 5 - Feb 6 includes taxes & fees 8.4/10 Very Good! (2,274 reviews) Clean room, good service Reviewed on Jan 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true®ionId=6360451) [See all 2,076 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F01%2F2026&endDate=14%2F01%2F2026®ionId=6360451) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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